The 100 Best Simpsons Episodes

As someone who has spent countless hours glued to my television screen, I must say that the list you’ve provided is a testament to the sheer genius of “The Simpsons“. Each episode on this list is a masterpiece in its own right, showcasing the show’s unique blend of humor, satire, and pop culture references.

Originally, this tale appeared in October 2014. To celebrate the 35th anniversary of the premiere of The Simpsons’ TV show, we’ve given it a fresh new take.

25 years deep into my endless binge of “The Simpsons” back in 2014, Vulture put together a list of their top 100 essential episodes. This list was meant to highlight the show’s consistent quality throughout the decades, covering various stages of its run. It didn’t just focus on the golden age from the mid-’90s, but also included more recent, and admittedly controversial, additions to the series.

Over the past ten years, The Simpsons has continued to grow and change, and so must this ranking. Since its initial publication, television’s longest-running sitcom has entered a new period of creativity, as the current creative team seeks innovative ways to explore the legacy of a show they grew up watching. Similar to today’s version of The Simpsons, this list is now the result of contributions from multiple writers over many years, each with their unique ideas about what constitutes a great episode of The Simpsons. It aims to capture the full spectrum of the show’s excellence beyond the few seasons often considered the best, meaning that newer episodes that expand our understanding of what makes an essential episode of The Simpsons may be included instead of some presumed classics.

In recognition of over 35 years and still going strong of fantastic “The Simpsons” episodes, here’s a collection of 100 episodes showcasing everything that the series excels at.

100. “A Mid-Childhood Night’s Dream” (Season 35, 2023)

Drawing inspiration from an episode of “The Sopranos” where Tony experiences food poisoning and hallucinatory nightmares about treachery, we find ourselves in a similar narrative scenario with Marge. After consuming contaminated food, she becomes embroiled in her subconscious apprehensions about Bart’s growth and development. This psychological thriller serves as an ode to dream narratives, delving into the origins of Marge’s unease and illness by presenting a non-linear sequence of imaginative and vividly animated vignettes.

One key factor that contributed significantly to the revival of “The Simpsons” is the introduction of the co-runner system by primary showrunner Matt Selman. This system allows a longtime “Simpsons” writer to guide each episode from conception to air, ensuring meticulous attention to detail. This change empowers producers to develop their episodes with a tone that reflects their unique creative vision, fostering a spirit of continuous innovation reminiscent of the show’s golden age. For instance, “A Mid-Childhood Night’s Dream” is a clear representation of Carolyn Omine’s style, as it delves deeply into emotional themes, reflecting her personal experiences at the time of writing, such as sending her son off to college. As a result, this episode stands out as one of the most emotionally intense episodes in “The Simpsons”, perhaps even the least humorous one. However, while it’s not suggested that the show should solely consist of meditative tone poems, having episodes like these that challenge and broaden the show’s boundaries is crucial for its longevity. Now, we can expect episodes that might make you laugh a little less but cry a lot more.

99. “Homerpalooza” (Season 7, 1996)

In essence, “The Simpsons” started out as a typical sitcom but evolved into something more, much like “Saturday Night Live,” which is known for its cultural commentary. In this context, “Homerpalooza” serves the same purpose, offering a Gen-X perspective on the Lollapalooza-like music festival scene. However, in this episode, Homer isn’t just an attendee; he experiences a cannonball to his stomach at Hullabalooza.

The episode succeeds at both telling the story of Homer’s desire to still be cool and making fun of what was cool at that time. Take one scene: Homer gets onstage and a shirtless member of the audience comments to his buddy in the de rigueur ironic tone, “Here comes that cannonball guy. He’s cool.” His buddy asks, “Are you being sarcastic, dude?” He responds, “I don’t even know anymore.” The ’90s!

98. “A Totally Fun Thing That Bart Will Never Do Again” (Season 23, 2012)

Bart seldom takes interest in things, but once he does, he’s completely committed. In “A Totally Fun Thing That Bart Will Never Do Again,” Bart sells all his possessions to fund a family cruise. Despite falling short, Marge and Lisa help out, and before long, the Simpsons are on a ship (never forget!). Everyone has a fantastic time, with Bart particularly enjoying himself until he overhears the cruise director, played by Steve Coogan, sing a tune about how passengers should seize the moment because they’ll soon return to their ordinary lives.

Bart becomes terrified, with Treat Williams offering assistance, Bart manages to convince everyone on the ship that a deadly virus has swept across the mainland, and they are now responsible for preserving humanity. It’s typical of Bart’s mischievous nature: he’s playing a trick, but it’s all in an attempt to avoid returning to the monotony of everyday life. One might find this behavior immature if we didn’t suspect that under different circumstances, Homer would probably act similarly.

97. “The Haw-Hawed Couple” (Season 18, 2006)

The Simpsons” has consistently excelled in incorporating popular culture, be it through satire of movies or inviting fitting guest stars. This ability remains both a strength and sometimes a challenge for the show today. In the episode titled “The Haw-Hawed Couple“, which is a play on “The Odd Couple“, we see references to “Goodfellas“, “Brokeback Mountain“, and an entire plot line centered around a fabricated “Harry Potter” book series.

Bart and Nelson develop an unexpected friendship when Bart is the sole kid at Nelson’s birthday party, which features a fake Spider-Man and Doctor Octopus. Despite Bart not wanting to be friends, he pretends for protection and other advantages, but everything comes crashing down once Nelson realizes their friendship was one-sided. Their friendship is brief, but every moment showcasing Nelson’s sensitive side is worth it. The humorous touch, where Bart clings to his Nelson vest while Nelson laughs, “Haw haw, I touched your heart!”, perfectly encapsulates the blend of humor and emotion that characterizes The Simpsons.

96. “Lisa’s Rival” (Season 6, 1994)

In most episodes of “The Simpsons,” Lisa stands out as Springfield’s intelligent citizen. The episode titled “Lisa’s Rival” explores what transpires when she encounters someone equally smart. Originating from an idea Conan O’Brien had prior to his move to Late Night, “Lisa’s Rival” introduces us to the character Allison Taylor, superbly voiced by Winona Ryder. Not only does Allison excel in school and play saxophone similarly to Lisa, she was even advanced a grade and surpasses her in skill on the instrument. This triggers an unfamiliar side of Lisa to emerge – a jealous, darker side.

One significant accomplishment of the show is its depiction of intelligence in a relatable and unique manner. The Simpsons, in part, explores the perspective of the intelligent, with Lisa often serving as a stand-in for the writers. The episode “Lisa’s Rival” stands out because it emphasizes that Lisa is not an unreachable super genius; she’s simply a bright young girl yearning for ordinary connections. Few Simpsons episodes capture Lisa’s longing for human connection as effectively as this one does.

95. “In Marge We Trust” (Season 8, 1997)

The exceptional quality of “In Marge We Trust” is underscored by the fact that the secondary storyline stands out as the more memorable one. While Marge assumes her role as “The Listen Lady” at church, casting a shadow over a dejected Reverend Lovejoy, an adventure unfolds for Homer, Bart, and Lisa as they seek to uncover the reason behind Homer’s head appearing on a Japanese box.

It turns out that Mr. Sparkle’s logo – a seemingly strange mix of a fish and a lightbulb – was merely a coincidental design, humorously referred to as “fish-bulb” by Bart Simpson in the show. However, its absurd backstory has since become one of the most recognizable symbols in the series, standing alongside iconic images such as the “I Choo-Choo-Choose You” Valentine and the Inanimate Carbon Rod.

94. “Clan of the Cave Mom” (Season 35, 2024)

In simpler terms, this episode of “The Simpsons” feels incredibly intense, much like a heavy metal song. Bart gets Milhouse into trouble on a school trip, leading to Marge fiercely defending Bart, reminiscent of a movie scene where Josh Hartnett stands up against a bully’s mom. The episode also features animated sequences resembling cave drawings, depicting the Simpson family’s prehistoric ancestors and nodding to the work of Genndy Tartakovsky, particularly his series “Primal”. These scenes are violent and action-packed, with Marge and Homer protecting their cave-babies from a giant wolf. The episode is well-written, and the best parts come when the two timelines converge in a climactic split-screen presentation. In essence, it’s exciting to see “The Simpsons” pay tribute to one of its contemporaries and showcase some intense action scenes.

93. “Duffless” (Season 4, 1993)

At Moe’s Tavern, a frequent hangout on the show, Homer is frequently intoxicated. He drives while drunk, does many things under the influence, but it’s in the episode “Duffless” that his drinking problem is addressed. After visiting the Duff Brewery and failing a breathalyzer test, Homer gets arrested and loses his driver’s license. Marge urges him to abstain from alcohol for a month, unaware of the challenge ahead. Struggling to stay sober, Homer confesses during an Alcoholics Anonymous meeting that in desperation for a taste of Duff beer, he secretly ate soil from beneath the bleachers at a football stadium.

In thirty days, Homer intends to compete in a race at Moe’s, but then he discovers something he cherishes more than Larry, Barney, and the man who calls him Bill: spending time with Marge. This tender conclusion caps off an authentic episode that resonates with a genuine sentiment: although we may not know what it feels like to travel to space, we can relate to the concern for our loved ones. The show’s relatability keeps “Duffless” down-to-earth, despite a cameo from the Duff Blimp.

92. “Gone Maggie Gone” (Season 20, 2009)

In a playful twist on both “The Da Vinci Code” and “National Treasure”, the episode titled “Gone Maggie Gone” employs a similar puzzle-solving, mystery-conspiracy format, but with a fresh, captivating spin. Here, Lisa assumes the role of Robert Langdon, embarking on a quest to find an ancient gem in order to trace missing friend Maggie.

Over numerous seasons, “The Simpsons” has masterfully absorbed and refract culture in such a way that the original source material becomes secondary to the episode itself. An illustrative instance of this is the episode titled “Gone Maggie Gone,” which remains fresh and incredibly humorous even though some of its references may be slightly outdated.

91. “Sideshow Bob Roberts” (Season 6, 1994)

“The episode ‘Sideshow Bob Roberts’ in the series, considered the most politically charged, skillfully explores how simple it can be to sway a complacent and agreeable populace. The character Birch Barlow, standing in for Rush Limbaugh, influences Mayor Quimby to free Sideshow Bob from prison. With public support behind him, Bob, an ex-con with a history of attempting to harm a young boy, surprisingly decides to run for mayor in Springfield.

Title “Sideshow Bob Roberts” (a nod to the Tim Robbins film) is filled with numerous references spanning decades, such as a nod to the Kennedy vs. Nixon debate, where Bob takes on the role of JFK. However, despite this abundance of references, it never feels weighed down by outdated satire. The humor flows swiftly and effortlessly, and it’s always enjoyable when Bart and Lisa team up to unmask Bob, who manages to win the election, as a massive fraud. In fact, “Sideshow Bob Roberts,” which criticizes both “cold-hearted” Republicans and “culpable” Democrats equally, seems to have grown even better with time. And it was already quite impressive before.

90. “I Married Marge” (Season 3, 1991)

In all Simpsons backstories, there’s a recurring theme: Marge’s pregnancies always seem to come at unexpected times. This idea is effectively conveyed in the episode “And Maggie Makes Three,” where Homer pulls out chunks of his hair upon learning about each of his children’s pregnancies – first Bart, then Lisa, and finally Maggie. However, “I Married Marge” concentrates solely on the story of their first child together.

In this special episode, a blurry pregnancy test sparks a memory for Marge, leading Homer to share their heartwarming love story (which we know isn’t from Barnacle Bill). The episode “I Married Marge” excels at filling us in on how Homer transformed from a boy into a husband and father in no time, while showing the deep affection between them. Although other beginnings for the Simpsons characters exist within their universe, there’s no denying that Homer proposing to Marge with an onion ring aligns perfectly with his endearing personality.

89. “Any Given Sundance” (Season 19, 2008)

Following her newfound love for producing documentaries, Lisa is inspired by a seemingly knowledgeable Principal Skinner to craft a film about her own family (the primary source of drama he points out). This leads to an intriguing episode that manages to incorporate guest appearances from Jim Jarmusch and John C. Reilly, a memorable sequence set to Spoon’s “I Turn My Camera On,” and a witty reference to The Simpsons Movie (“No more Simpsons movies! One was enough.”).

Titled “Any Given Sundance,” this episode shares similarities with Season Six’s “A Star Is Burns” but delves deeper into Lisa’s perspective, emphasizing her critical view of her parents and brother, as well as her personal judgments. While we’ve caught glimpses of her thoughts throughout the seasons, this episode offers a more profound exploration. It also serves as an insightful critique of the film festival world, with lines like “I preferred this movie to that little girl’s because I saw it today.

88. “Springfield Up” (Season 18, 2007)

In the world of “The Simpsons”, the sequence of events leading up to Bart’s birth has been altered so frequently that it becomes challenging to distinguish truth from fiction. The latest perspective on Homer and Marge’s past is presented through Springfield Up, a documentary-style parody reminiscent of the U.K.’s Up series. This reinterpretation stands out as one of the more effective retellings in recent seasons.

Filmmaker Declan Desmond (portrayed by Eric Idle from Monty Python) periodically visits Springfield residents every eight years. His purpose is to document their transformation from childhood to adulthood, as it seems everyone in Springfield attended the same school. This storyline might not reflect the actual history of The Simpsons, but it presents an entertaining, alternate version that could have easily been accepted and convincing. The show often incorporates contradictory details into its background, which adds to the excitement of following the numerous seasons of The Simpsons.

87. “All’s Fair in Oven War” (Season 16, 2004)

As a die-hard movie buff, I can’t help but rave about “All’s Fair in Oven War,” a hysterical compilation of two classic Simpsons tales! The central narrative revolves around Marge, who resorts to deception to triumph in a baking competition. Her motivation? To break free from the label of “the spouse of a man who skips work.

Unlike traditional sitcoms, each episode of this show doesn’t follow a single format. An episode might focus on one story, two, or even three stories. The episode “All’s Fair in Oven War” exemplifies the series’ remarkable knack for weaving together two distinct yet wholly satisfying narratives.

86. “Natural Born Kissers” (Season 9, 1998)

In a new twist, “The Simpsons” delves into a more open and explicit discussion of sexuality. While it has been suggested through innuendo that Homer and Marge share a strong intimate relationship (or a “snuggle life,” as Marge might put it), the episode “Natural Born Kissers” makes this assumption more prominent by focusing on their rekindled passion, which involves enjoying their affection in public.

In a non-traditional manner, the series “The Simpsons” skillfully paints a picture of a marriage using various vignettes. The show deserves praise for its boldness in tackling mature themes. Interestingly, the censors were surprised by the frank depiction of adult content in one episode, but the producers bravely stood their ground. By the way, the episode also includes a side-splitting B plot where Bart and Lisa stumble upon an alternate ending to the classic film “Casablanca“.

85. “The Principal and the Pauper” (Season 9, 1997)

“The Principal and the Pauper” is the WORST. EPISODE. EVER. for many Simpsons fans who care too much about canon. That’s a shame, because it’s actually an interesting and vastly underrated exploration of a character we thought we knew for years. During a surprise party celebrating Seymour Skinner’s run as principal of Springfield Elementary for 20 years, a mysterious guest crashes the festivities. He claims he’s the REAL Seymour Skinner, and our Seymour is actually an impostor named Armin Tamzarian, a claim that’s later verified. They served together in Vietnam, but when Skinner goes missing, Tamzarian takes on his identity.

Before the era of “Mad Men,” there’s a plot twist in which Tamzarian takes on the role of Skinner out of affection to hide the truth about Seymour’s disappearance from Agnes, his mother. This episode also serves as a subtle commentary on fans of The Simpsons who often resist change. After the original Skinner is relocated, Judge Snyder forbids anyone from discussing the incident under threat of punishment. Interestingly enough, the “Pauper” episode, despite the judge’s warning, has become one of the MOST FREQUENTLY DEBATED EPISODES IN THE SERIES’ HISTORY.

84. “Grade School Confidential” (Season 8, 1997)

This episode showcases how The Simpsons excels in creating an intricate world of distinctive, funny characters, each with their own distinct personalities and driving forces. In this particular episode, the relationship between Principal Skinner and Miss Krabappel unfolds – a romantic entanglement that takes place fittingly at Martin’s disheartening birthday celebration. However, Bart witnesses the entire affair, causing the couple to offer him a bribe to stay quiet and act as an intermediary.

In a surprising twist, this mature installment doesn’t focus on Bart; instead, it delves into the emotional journey of the adult characters, Marge and Ned Flanders, as they find solace in each other’s sorrow. Though it includes familiar humor (like Homer mispronouncing Edna Krabappel’s name, Ralph witnessing their kiss, and the infamous “Sex Cauldron” scene), what truly sets this episode apart is its ability to elicit empathy for characters often relegated to supporting roles – characters who typically serve as targets for Bart’s antics.

83. “And Maggie Makes Three” (Season 6, 1995)

In another instance of Homer aspiring for an ideal job, he decides to leave his power plant position once all his debts are settled, opting instead to work at a bowling alley. Although the task is straightforward, he takes pleasure in it and excels at it. However, life takes an unexpected turn when Marge becomes pregnant with Maggie. This new role as a father forces him to juggle his aspirations with his parental duties. The finale of this particular episode delivers one of the series’ most poignant emotional blows, leaving viewers reflective – for those who have witnessed it, here’s a reminder; for the uninitiated, feel free to move on and revisit later.

Following a humbling plea to reclaim my job at the power plant, Mr. Burns reinstates me at my post, with a chilling sign that reads, “Remember, you’re here forever.” It’s a cruel and disheartening reminder. Yet, in the final scene, this sign is adorned with pictures of Maggie, some strategically placed to obscure certain letters, now reading, “Do It for Her.” This simple image carries profound meaning – life often demands us to undertake tasks we’d rather not, for the sake of those we cherish. And sometimes, it’s a sacrifice worth making.

82. “Moe Baby Blues” (Season 14, 2003)

Moe is often portrayed as The Simpsons’ most troubled character, but there are moments when his unique blend of darkness and humor can be particularly poignant. In a typical Moe scenario, the central plot of “Moe Baby Blues” unfolds with a suicide attempt, where he unexpectedly catches Maggie after she was propelled into the air following a car accident. This incident marks the beginning of an unusual yet endearing bond between the two characters that’s hard to ignore.

After discovering Alice in Underpants, a spin-off of the movie he’d recently watched – Alice in Wonderland, Moe admires, “It’s delightful being with someone who doesn’t grasp my harsh words.” The blend of darkness and lightness in this episode makes it captivating. In essence, The Simpsons’ world mirrors the cycle in Groundhog Day where Bill Murray continuously explores various methods to end his life. Despite knowing that Moe’s world will reset, his happiness is refreshing.

81. “Skinner’s Sense of Snow” (Season 12, 2000)

During a severe blizzard, an unusual situation unfolds at Springfield Elementary as Principal Skinner and Groundskeeper Willie are left with the students. The atmosphere turns chaotic. To preserve his record of keeping the school open, Skinner disregards the harsh weather conditions and insists students attend on the eve of Christmas break. Using tactics learned from his military background, Skinner attempts to maintain discipline, but the students, led by Bart and Nelson, defy him and end up confining their principal within a burlap sack.

Skinner’s Sense of Snow” transforms the dreadful reality for kids – attending school when all others are closed due to a storm – into an exhilarating fantasy instead. This is a charming throwback that The Simpsons, known for tackling mature themes, has seldom touched upon.

80. “Treehouse of Horror XXXIII” (Season 34, 2022)

The continued ability of “The Simpsons” to produce innovative and laugh-out-loud “Treehouse of Horror” episodes, even at episode 33, demonstrates just how much creative potential remains in animating these vibrant Springfield characters into fresh and unexpected scenarios. In this latest trio of spine-tingling tales, “The Pookadook,” a playful take on the horror film “The Babadook” with Marge being possessed by a dark creature from a picture book, and “Death Tome,” an homage to the manga series “Death Note” creatively transformed into a visually striking anime style, both explore literary horror themes and are filled with numerous Easter eggs. Bart Simpson makes a comeback in the Lisa-centric “Death Tome”; Maggie’s bookshelf in “The Pookadook” showcases classic childhood titles like “S’up Moon” and “Harold the Delusional Vandal,” which, in retrospect, would have been perfect for the 2024 movie adaptation.

What makes “Treehouse of Horror” a legend is the climax of the third act, “Simpsons World.” This creative parody of Westworld, set within a theme park for Simpsons enthusiasts named after the streaming platform dedicated to all things Simpsons (which ceased to exist due to Disney’s acquisition of Fox), is packed with references to earlier episodes that would delight hard-core fans. When a Simpsons World employee discusses her date with someone from the props department, she casually remarks, “He’s so arrogant. I mean, he manages Sideshow Bob’s rakes. We get it, there are plenty of rakes.” And when Lisa, in true Lisa fashion, is the first to recognize that she and her family have become robots, she exclaims, “We’re replicants for an ancient TV show that lost its luster after season 45!” Lines like these, and many others, are just as funny as anything written during the show’s ’90s and early 2000s heyday.

79. “The Saga of Carl” (Season 24, 2013)

At first glance, “The Saga of Carl” might appear to be an ordinary episode featuring the show’s characters traveling to a distant land and poking fun at it. However, this episode wouldn’t make our list if that were its only purpose. Although the storyline follows Homer, Moe, and Lenny as they pursue Carl who has run off with their lottery earnings to Iceland, the episode delves deeper into the nuances of male camaraderie, offering a thoughtful perspective on this topic.

Midway through the episode, Homer ponders, “Fellas, could it be that Carl was correct? Are we merely friends who share activities instead of truly confiding in each other, perhaps just lonely souls?” This thought is poignantly illustrated in a heart-wrenching 20-second sequence (accompanied by a Sigur Rós soundtrack) showcasing Homer, Moe, Lenny, and Carl sitting or standing side by side, their expressions unchanging as the backdrop transitions. This scene beautifully encapsulates the concept of ‘side-by-side’ camaraderie, where friends engage in shared activities without much verbal interaction. Once more, “The Saga of Carl” demonstrates that The Simpsons is capable of exploring deep, intimate narratives.

78. “When Flanders Failed” (Season 3, 1991)

Ned Flanders consistently excels in the universe of “The Simpsons,” unlike other characters who are often characterized by their imperfections such as Moe’s absent love life, Skinner’s overbearing relationship with his mother, and Homer’s inherent lack of intelligence. The episode “When Flanders Failed” presents a change in the dynamic between Homer and Flanders, marking the rare occasion where we witness Flanders experiencing difficulties instead of his typically steady neighbor.

In this episode, when Homer gets a wishbone and wishes for Ned’s new Leftorium to fail (which is preferable to him than facing death), we witness the same misfortunes that usually affect Homer befalling Ned instead. This storyline takes on a more melancholic tone compared to typical episodes. However, in a heartwarming turn of events reminiscent of “It’s a Wonderful Life“, Homer manages to make amends by rallying his friends together to help revive Ned’s business.

77. “Today, I Am a Clown” (Season 15, 2003)

Exploring further the Jewish heritage of Krusty in the episode titled “Today I Am a Clown,” we follow Krusty as he walks his new puppy along Springfield’s Jewish Walk of Fame, which he unexpectedly acquired through Lisa’s help. The narrative then unfolds into a humorous yet emotional odyssey reminiscent of “The Jazz Singer.” As the story progresses, Krusty discovers that his eligibility for the Walk of Fame was denied due to him never having had a Bar Mitzvah. Intrigued by this revelation, Bart and Lisa delve deeper into Krusty’s past and uncover that his father, Rabbi Hyman Krustofsky, refused to perform the ceremony because he feared that young Krusty (originally known as Herschel Krustofsky) would not take it seriously.

This episode carries both an emotional depth and a weighty theme, addressing the clash between different generational perspectives with as much gravity as the two adaptations of “The Jazz Singer” it satirizes. Some of the humor is sophisticated enough to approach the type of culturally-specific wit found in Woody Allen’s works; when Bart asks Lisa why she knows so much about Judaism, her response is cleverly witty: “I have an imaginary Jewish friend named Rachel Cohen who just got into Brandeis.

76. “Bart Sells His Soul” (Season 7, 1995)

In a bid to demonstrate that souls don’t exist, Bart decides to “auction off” his for an affordable $5 – just enough to get a mediocre set of inflatable toys. This transaction means nothing to Bart, but strange occurrences start happening: Electronic doors refuse to open, and he loses interest in Itchy & Scratchy cartoons. Desperate to regain what he’s sold, Bart attempts to repurchase his soul from Milhouse, only to discover that it was previously traded to the Comic Book Guy. The Comic Book Guy then reveals that someone else had already bought Bart’s soul from him.

In an exceptional episode titled “Bart Sells His Soul,” Bart discovers the concept of a soul in an unusual manner, leading him to feel humbled. Interestingly, Lisa, who often questions such matters, already understands the truth about souls. The storyline takes a chilling turn as Bart experiences a haunting nightmare where he’s the only child in Springfield without a soul. The blend of supernatural themes, emotional turmoil, and a touch of Uncle Moe’s Family Feedbag is what makes this episode one of Matt Groening’s favorites.

75. “Homer and Apu” (Season 5, 1994)

This episode sheds light on an apparent query: Who couldn’t use the Kwik-E-Mart? It’s clearly Apu. A recurring figure in the Simpsons world, Apu typically operates within the boundaries of the convenience store where he works. But when Apu is caught selling outdated meats, mainly to Homer, and is then dismissed, he finds himself beyond those limits. Unavoidably, this situation takes him to the house of the one who betrayed him.

One way to rephrase the given statement in a more natural and easy-to-read manner could be: “What makes ‘Homer and Apu’ a timeless tale is its unique approach where it places a secondary character squarely within the core group’s sphere, yet keeps Homer as the instigator of the ensuing chaos. The audience gains a deeper understanding of Apu’s life and dedication to his job, but it’s Homer who sets off the series of adventures. From crushing a tiny camera inside Kent Brockman’s enormous novelty hat to essentially ruining a journey to the summit of an Indian mountain, this episode is a standout for both characters.

74. “Treehouse of Horror VI” (Season 7, 1995)

One of the wonderful things about Treehouse of Horror episodes is that they allow the show’s writers to go absolutely nuts and indulge in the weirdest, cruelest, most cutting parts of their imaginations. The first segment in this sixth entry — “Attack of the 50-Foot Eyesores” — is the latter. An atmospheric storm brings giant fast-food and other capitalist mascots to life, and they go on a destructive tear through town. At story’s end, Kent Brockman intones portentously, “Even as I speak, the scourge of advertising could be headed towards your town!” Cut to commercial.

As a movie critic, I found “Nightmare on Evergreen Terrace” to be a chilling and innovative take on the classic horror trope made famous by Wes Craven: “dream if you dare, die if you must.” The episode takes a dark turn when Martin, a student, dies in class after being frightened in his dreams, only for the sheet covering his gurney to slip off, revealing his terror-stricken face. The ensuing screams are enough to make one’s hair stand on end. The gurney is then accidentally wheeled into the kindergarten class, adding another layer of horror to an already tense scene.

73. “How I Spent My Strummer Vacation” (Season 14, 2002)

One standout aspect of “The Simpsons” is its impressive roster of guest stars it’s managed to secure throughout its 25-year broadcast. This episode underscores that it’s not only great at attracting these stars, but also at integrating them effectively. Homer has had numerous jobs, yet if he could pick one permanent profession, he might opt for being a renowned musician. He appears to be quite happy living the life of a rock star, minus the sex and drugs, in “How I Spent My Strummer Vacation.” Following a quick tutorial in rock music from Mick Jagger, Keith Richards, Tom Petty, Lenny Kravitz, Elvis Costello, and Brian Setzer, Homer lands a gig as an opening act for these musicians at a charity concert.

As far as he’s concerned: Homer is merely a supporting act, yet when he spots his family applauding him from the crowd, he adopts an air of stardom. The plot twist is effective because it mirrors how “Strummer” portrays genuine rock legends. Mick and Keith, the camp counselors, are depicted as individuals more concerned with economizing on oatmeal and installing storm windows rather than indulging in their rock ‘n’ roll spirit.

72. “$pringfield (Or How I Learned to Stop Worrying and Love Legalized Gambling)” (Season 5, 1993)

As a movie critic, I found that “Springfield (Or, How I Learned to Stop Worrying and Love Legalized Gambling)” serves as a thought-provoking exploration of the far-reaching impacts gambling can have on a close-knit community. This narrative unfolds with Homer transitioning into a blackjack dealer, Marge succumbing to a compulsive gambling habit, Bart embarking on a venture to establish his own casino, Lisa experiencing neglect, and Mr. Burns spiraling into sheer insanity.

One of the initial episodes featuring a multitude of Springfield residents is titled “$pringfield”. This episode resembles the expansive feel and character-rich nature of “The Simpsons Movie“. However, “$pringfield” is particularly renowned for the episode where Mr. Burns transforms into Howard Hughes, which is arguably one of the most outrageous, absurd storylines in the show’s history.

71. “Moe’N’a Lisa” (Season 18, 2006)

In this episode, we find two longtime outcasts from Springfield – Moe and Lisa – unexpectedly forming a friendship. This happens when Lisa organizes Moe’s melancholic, potentially suicidal musings, which he refers to as “brain goo,” into a poem. Their collaboration results in a poem that becomes a hit, leading them to the satirical Wordloaf Literary Conference, a witty take on the Bread Loaf Conference. The ensuing events offer a humorous critique of the literary world.

In no shortage of references, only The Simpsons could manage an episode like this after an NFL game. Be it Gore Vidal admitting he named Burr from seeing it on a billboard for Eskimo Pie, Thomas Wolfe asking for everyone’s leftover garlic mashed potatoes, or the heated feud between Michael Chabon and Jonathan Franzen (all four lending their own voices), the show masterfully transforms these literary titans into comic figures. It’s this perfect blend of high culture, popular culture, and slapstick humor that we crave in the finest episodes.

70. “Hurricane Neddy” (Season 8, 1996)

Briefly: It takes Homer, the perpetual chaos, to make the normally composed Ned lose his cool.

In a surprising turn of events, we find ourselves delving into the unconventional backstory of Ned: How He Came to Embrace the Doodily. “Hurricane Neddy” might seem like a humorously perilous episode, yet it’s also a profound exploration of character development. As nonsensical musings start to align, we realize that Ned has been suppressing his feelings since childhood. The Simpsons may be an animated series, but its insights into human psychology are remarkably deep.

69. “Mr. Lisa Goes to Washington” (Season 3, 1991)

This installment serves as an early demonstration of Lisa’s relentless dedication when she latches onto a cause she passionately supports. In this case, the ’cause’ is none other than America itself, which she encounters head-on after winning an essay competition that sends her to Washington D.C. There, she witnesses her local congressman accepting a bribe to destroy a forest in Springfield, forcing her to confront the flaws and corruption within the nation.

Mr. Lisa” is similar to numerous episodes of “The Simpsons” where they travel to different cities or countries and engage with local attractions – like when Bart was told to get out of the Spirit of St. Louis – and serves as a precursor for a multitude of stories featuring Lisa in conflict, such as her battles against Malibu Stacy and her decision to become a vegetarian.

68. “Selma’s Choice” (Season 4, 1993)

In her final video message before passing away, Aunt Gladys advises Marge’s sisters, Patty and Selma, against dying without companionship. As a result, Selma embarks on a quest to find a compatible partner. Despite her efforts, she doesn’t succeed, but gets an opportunity to display her nurturing abilities when she takes Bart and Lisa to Duff Gardens. However, the trip turns out to be chaotic.

He finds himself trapped on a roller coaster, believing herself to be the Lizard Queen. In her moment of surrender, she understands: The “smaller version of me I could cradle in my arms” doesn’t necessarily have to be a child; it can also be a pet lizard named Jub-Jub. Patty and Selma embody qualities that are opposite from Marge’s – they are cynical, rude, and un-beehived. However, “Selma’s Choice” skillfully invites us to feel for one of the troublesome twins, demonstrating that even the extended Simpsons clan can be as intricate as the main family.

67. “The Seemingly Never-Ending Story” (Season 17, 2006)

During an apparently harmless stroll through some nearby caves, Homer carelessly touches a massive stalactite, causing a hole to appear beneath him, which leads to the entire family plummeting down. Trapped far underground, particularly Homer who is wedged in a tunnel due to his size, Lisa starts narrating a tale to him. In this narrative, Mr. Burns begins telling another story. Then, within Burns’ story, Moe starts spinning a yarn… and so the tales continue.

The situation turned out to be quite absurdly entertaining, culminating in a scene reminiscent of “Good, Bad and the Ugly” standoffs, but with a unique twist involving an aggressive goat and a bracelet that will leave you amazed – it’s one of the best jokes “The Simpsons” has produced in the past decade. This episode is remarkable for its intricacy, as its structure manages to be both foolishly amusing and stunningly elegant at the same time.

66. “Like Father Like Clown” (Season 3, 1991)

You could probably organize a wickedly entertaining marathon consisting only of episodes in which Krusty interacts with Bart and/or Lisa. This one follows up on season one’s “Krusty Gets Busted,” in which Bart saves Krusty from prison by revealing that it was Sideshow Bob who actually robbed the Kwik-E-Mart. (A key episode, it seems, as it would also kick off the Sideshow Bob story line that would result in our No. 1 pick, “Cape Feare.”) Here, after missing several dinners at the Simpsons’ house, promised to Bart after he got Krusty out of his jam, Krusty reveals that he is Jewish and that he is estranged from his rabbi father.

Jackie Mason portrays Rabbi Hyman Krustofsky in an episode overflowing with Jewish humor, delicately presented. The Lower East Side of Springfield serves as the backdrop, where a young Krusty is seen performing at a Catskills rabbi gathering, echoing elements from The Jazz Singer. Notably, “Like Father Like Clown” demonstrated that this animated family sitcom, centered on the Simpsons family, can also explore other characters’ histories, drawing laughter, emotion, and relatability.

65. “Homer Badman” (Season 6, 1994)

In the episode “Homer Badman,” every moment is packed with classic scenes. It starts with a visit to a candy expo, where Homer swipes a unique gummy. Later, the babysitter he hired for the kids accuses him of inappropriate behavior, despite his intention being to retrieve the gummy from her candy container labeled “sweet-sweet.” The media and a TV movie (Homer S.: Portrait of an Ass-Grabber) portray him as a monster.

The “Homer Badman” episode isn’t an easy feat to execute: For much of its duration, our apparent protagonist is branded as a pervert. However, despite the doubts harbored by his family, we, the audience, understand Homer’s innocence – after all, who could commit such heinous acts when one desires to live under the sea?

64. “Kamp Krusty” (Season 4, 1992)

Among the darker episodes of “The Simpsons,” “Kamp Krusty” portrays Bart and Lisa’s dismay at the dismal summer camp environment, bearing the title. The management of this lakeside inferno has been outsourced to Mr. Black, a bureaucratic functionary who then assigns tasks to his goons, Jimbo, Dolph, and Kearney. (Bart: “Aren’t we supposed to roast marshmallows?” Dolph: “Shut up and eat your pinecone!”) As the children are forced to consume Krusty Brand imitation porridge (“nine out of ten orphans can’t tell the difference”) and endure long hikes, factory work, they start a rebellion led by Bart.

In the beginning of “Kamp Krusty,” Bart scribbles on the chalkboard that this punishment isn’t dull and without purpose. This hints at the hardships to follow. Similar to many early episodes, it relentlessly pursues its main plot and maintains a consistent tone. If even one joke had gone wrong, the tone could have shifted drastically from darkly humorous to harshly unpleasant in an instant. However, none of the jokes miss their mark. Lisa says, “I feel like I’m going to die,” to which Bart replies, “We’re all going to die, Lise.” Later, Lisa clarifies, “I meant soon,” and Bart responds, “So did I.

63. “Whacking Day” (Season 4, 1993)

In Springfield, the strong sense of community, though powerful, often leads to a lack of questioning unusual customs like Whacking Day, an event modeled after a real annual event in Texas where people collectively hunt and harm snakes. Initially, animal lover Lisa voices her opposition, but it’s Bart who cleverly steps in to prevent the harmful actions.

Bart is kicked out of school for crashing a tractor into Superintendent Chalmers, leading him to be taught at home by Marge. He then develops a love for reading after discovering a book about a boy who goes off to war. When Bart uncovers the truth that Whacking Day is a fraud, he teams up with Lisa to entice the town’s snake population into their house by inviting Barry White over. Shocked and disgusted by the celebration (“You people make me sick!”), White uses his deep voice to create vibrations that draw the snakes. This outlandish storyline is typical of the type of plots that The Simpsons excels in.

62. “Trilogy of Error” (Season 12, 2001)

In one of the show’s most challenging and creatively inventive episodes, titled “Trilogy of Error,” the narrative is divided into Homer’s Day, Lisa’s Day, and Bart’s Day, with each segment intertwining. This storytelling approach resembles movies like “Run Lola Run” and “Go,” but it features poor grammar, fabricated addresses, bungling simpletons without thumbs, and hillbillies giving lifts to hitchhikers.

As a passionate film enthusiast, I can’t help but marvel at “The Trilogy of Error.” The story unfolds when I, in a familiar predicament, miss my bus due to tinkering with Linguo, my linguistics robot. In a twist of fate, Krusty and Teeny offer me a ride to the hitherto unmentioned West Springfield Elementary School. Despite the initial setback, the narrative doesn’t falter; instead, it gathers pace, culminating in a delightfully satisfying climax that keeps me hooked from start to finish. This episode is truly unique and stands out amongst its peers.

61. “Steal This Episode” (Season 25, 2014)

A person who says that “The Simpsons” hasn’t been good for years is likely not up-to-date with the show, as evidenced by their lack of knowledge about episodes like “Steal This Episode,” the 539th installment which feels just as relevant and engaging as the early episodes. In this particular episode, Homer grows tired of paying excessive amounts for movies that are preceded by lengthy commercials and trailers, so he resorts to downloading them illegally from the internet instead.

Homer’s time on the run didn’t stretch for long, and eventually he surrendered. His court case drew high-profile attendees like Judd Apatow, Seth Rogen, and other prominent figures from Hollywood who accused Homer of both creative and financial theft. In a heartfelt speech, Homer argued that everyone is simply trying to make as much money as they can, echoing Lisa’s words. “Steal This Episode” avoids taking a side in the pirates versus producers battle, it doesn’t need to. However, what makes this series stand out (in a positive way) is its ability to remain hilarious even at this late stage of the game.

60. “Bart’s Comet” (Season 6, 1995)

In a magazine called Time, writers speculated that if a comet struck Earth, it might resemble an episode of The Simpsons, where Bart accidentally finds out about a comet heading towards Springfield. Although the entire 22 minutes are enjoyable, the episode becomes extraordinary when the Simpsons and multiple recurring characters crowd into Ned’s bomb shelter. This scene recalls the crowded cabin from A Night at the Opera, but with everyone vying to show they deserve survival because the door won’t shut, and someone must be removed.

As a cinema enthusiast, I’d rephrase it as follows: In this crazy world we live in, it’s essential to find some laughter, and Krusty certainly delivers! Even the religious chatterboxes, the Lovejoys, make the cut. Unfortunately, Flanders is deemed as the odd one out, and he’s asked to leave. As Ned sings a melancholic “Que Será, Será (Whatever Will Be, Will Be)” in the background, things quickly spiral into turmoil, and Homer follows his neighbor out of the shelter. Before long, everyone else joins them. The message here is poignant: it’s better to exit peacefully than to endure discord. Springfield truly embodies a community, with its characters offering a mix of humor and familiarity that makes the show so delightful. “Bart’s Comet” is a testament to the wit that ensues when these unique personalities collide.

59. “Halloween of Horror” (Season 27, 2015)

After being on-air for as long as “The Simpsons” and covering as vast a landscape as it has, as well as having an impact comparable to that iconic series, it can be challenging to create something truly distinct. However, while the later seasons may not consistently churn out masterpieces, the rare gems are just as exceptional as the show ever was. “Halloween of Horror” is one such exceptional episode.

Correct: “Indeed, it’s not ‘Treehouse’ we’re discussing, but rather “Halloween of Horror.” After 27 seasons, the show opted for an authentic Halloween episode. Given the established tradition of “Treehouse of Horror,” there was a wealth of material for the writers to draw upon as they delved into making fun of the holiday. When we speak about The Simpsons at its peak, we refer to filling television with as many jokes, ideas, and parodies as it can accommodate, and this episode embodies that density, touching on eight different aspects of Halloween. As these events unfold, “Halloween of Horror” also tells two heartwarming stories about the bond between kids and Halloween, and the efforts of parents to shield their children from adult realities. The writing and direction effectively depict the world from both Bart and Lisa’s perspective as well as Homer and Marge’s within the same episode. No other show has managed big and small storytelling as seamlessly as The Simpsons, and this is a remarkable demonstration of that skill.

58. “Eternal Moonshine of a Spotless Mind” (Season 19, 2007)

2008 saw “Eternal Moonshine of the Simpsons Mind” take home the Emmy for Outstanding Animated Program (under an hour). However, it’s not just animation that makes it exceptional; its quality is worthy of an Outstanding Comedy Series nomination. The plot revolves around Homer, who, after taking a potent “Forget-Me-Shot” at Moe’s, finds himself unable to remember the previous day’s events. In a style reminiscent of “Eternal Sunshine of the Spotless Mind,” “Memento,” and even “El Viaje Misterioso de Nuestro Jomer,” Homer must piece together a painful memory he inadvertently erased through drinking. Hopefully, that’s clear!

It makes perfect sense in the actual episode, which includes a visually rich parody of those “Take a Photo of Yourself Once a Day for Five Years” videos. Although the multi-layered, mind-bending “Eternal Moonshine” is all about forgetting, it’s an episode whose delightful structure makes it a cinch to remember.

57. “The Last Temptation of Homer” (Season 5, 1993)

In terms of tone, “The Last Temptation of Homer” stands as one of the series’ most impressive accomplishments. Previous episodes like “Life on the Fast Lane” and “Colonel Homer” tackled infidelity, but this particular episode outshines them all. Here, Homer encounters Mindy, a new female coworker who seems to be his ideal match, elevating the show to new heights.

The show expertly portrays Mindy’s character, brilliantly brought to life by Michelle Pfeiffer. Instead of presenting her as a typical flirt or seductress, the writers make her relatable – she’s just as taken aback by the situation as Homer is. Unlike portrayals that might emphasize her being lustful or playful, there’s an undercurrent of nervousness and discomfort in her actions. The episode also avoids stereotyping Homer by allowing him to genuinely experience temptation. What’s striking about this episode is how it subtly communicates the idea that marriage isn’t about never feeling tempted, but recognizing that what you have is more valuable.

56. “Bartless” (Season 34, 2023)

The episode “Bartless” from The Simpsons has a heartwarming twist on the classic question: “Of course we love our son, but do we like him?” This episode presents Bart as a lovable character, despite his mischievous behavior. In this storyline, Bart gets into trouble for vandalizing library books, leading Homer and Marge to ponder what their lives would be like if Bart had never existed. In an alternate reality, they find themselves in improved circumstances – Marge is a successful veterinarian at an animal hospital reminiscent of Grey’s Anatomy, while Homer operates the scoreboard at Isotope Stadium. They adopt an orphaned Bart, who continues to cause chaos but also brings joy and enrichment to their lives. The alternate reality setting offers fresh jokes, but the real appeal lies in the subtle details, such as Bart’s reinterpretation of a Richard Scarry-style picture book and a humorous background gag involving Ralph and the purple crayon.

55. “Mr. Plow” (Season 4, 1992)

To those who initially watched “The Simpsons” as young children, countless cultural references were subtly embedded within their minds, ready to be recalled later. Who among 10-year-olds recognized that the rope bridge scene alluded to William Friedkin’s Sorcerer, or that the flashback to sober Barney borrowed its slow-dissolve montage from Dr. Jekyll and Mr. Hyde, or that Bart getting hit by a snowball was a tribute to the end of Bonnie and Clyde? Naturally, though, it’s the song in this episode that everyone recalls most vividly.

After the Springfield Auto Show, Homer purchases a large plow. Earning money by clearing snow from driveways and roads, he coins himself as “Mr. Plow.” Soon after, Barney acquires a larger truck, sparking a friendly rivalry between the two. The narrative is clear and includes several self-referential jokes, such as Homer’s comment about his late-night commercial: “It might be on a terrible channel, but The Simpsons are on TV!” The catchy slogan “I’m Mr. Plow” is easy for children to remember and has a simple, palindromic quality.

54. “Lisa’s Wedding” (Season 6, 1995)

2010 finds us here, while for those watching “Lisa’s Wedding” in 1995, it might have seemed an unreachable future, one where The Simpsons may no longer be on television. (A chuckle!) However, not much has evolved: Homer and Marge remain a couple, Maggie continues to stay mum, Bart wreaks havoc, but now in his career rather than at home, and Lisa retains her intelligence. She’s enrolled as a student at Eastern University, where she encounters Hugh (played by Mandy Patinkin). He is intelligent, handsome, and appreciates the charm of Jim Carrey, so when he proposes to Lisa, she promptly agrees.

I, filled with joy, journey alongside Lisa and Hugh to Springfield for their upcoming nuptials, feeling as lighthearted as a breeze. However, this seemingly alike duo soon discovers the profound differences that lie beneath their surface. The captivating film, “Lisa’s Wedding,” is brimming with witty predictions of what may come, but it delves deeper into the profound love one little girl harbors for her father, despite his occasional challenges.

53. “Brick Like Me” (Season 25, 2014)

Initially, when news broke about a Lego episode, it was challenging not to harbor doubts, considering its apparent connection to product promotion. However, any reservations proved unwarranted. The episode titled “Brick Like Me” is endearing and visionary, demonstrating impressive production quality and storytelling prowess. It narrates the tale of Homer, who inadvertently travels to a fictional Lego-Springfield when Lisa chooses to spend time with her friends instead of joining him in a Lego competition.

Homer and Lisa’s stories are often the most heartwarming, as you can see from this list filled with them. In this particular case, “Brick Like Me” does a fantastic job of making us reflect on the deepest aspects of parenthood – the journey of watching your child grow up. Beneath all the Lego sounds and visuals lies an episode exploring one of life’s most profound experiences.

52. “Who Shot Mr. Burns?: Part 1” (Season 6, 1995)

Back in the day, it’s simple to overlook the immense impact of the “Who Shot Mr. Burns?” saga when it originally aired. This storyline was modeled after Dallas’s “Who shot J.R.?” plot twist, but it certainly held its own weight. The first part, airing as the season six finale, skillfully established that nearly every character in Springfield had a valid reason to want to take down Mr. Burns. He had transformed from an ordinary villain into a cartoonish supervillain, going so far as to steal oil from the school and block out the sun.

In the first episode of season seven, Lisa teamed up with Chief Wiggum to track down the villain, drawing inspiration from the style of “Twin Peaks” throughout the process. The show aimed to generate excitement around its cliffhanger from season six, and it certainly achieved that goal. Over the summer, viewers engaged in heated discussions, trying to predict the identity of the culprit and win the contest. They also frequented the newly established Springfield.com (this episode is often recognized as one of the earliest successful internet integrations by a television show). The mystery was surprisingly well-crafted, and it concluded in a way that felt true to the Simpsons’ unique style.

51. “The Way We Was” (Season 2, 1991)

In this rendition, we find that origin stories are by no means fresh concepts. However, here, we’re discussing one that carries significance. If you consider early Simpsons episodes as narratives about a family, whereas later ones expanded to encompass a town, then “The Way We Was” marked the initial phase in the lengthy journey leading up to Bart, Lisa, and Maggie.

In high school for the first time, Marge finds herself in detention. This is familiar territory for Homer, who upon seeing her walk in, experiences an immediate romantic attraction. After a session of French tutoring, some deceitful maneuvers, and a disastrous prom night orchestrated by the know-it-all Artie Ziff (voiced by Jon Lovitz), Homer confesses one of the most heartfelt statements he’s ever made on the show: “I have a confession. Once we pull over, I plan to give you a hug and a kiss. After that, I won’t be able to let go.

50. “Rosebud” (Season 5, 1993)

In “Rosebud,” I found a side of Mr. Burns that wasn’t purely malicious. There were moments when he displayed kindness, albeit in unusual circumstances. For instance, when he discovered that Maggie had his beloved teddy bear, I saw him at his most generous and ruthless simultaneously. He offered the Simpsons an enormous sum of money and three Hawaiian islands for the toy, but as much as it hurt me to turn down such a deal, I knew how much my daughter cherished that stuffed animal. So, in this instance, Mr. Burns wasn’t just a monster, he was complex, displaying both his best and worst traits.

Following a string of failed heists, Burns instead intercepts all the beer deliveries bound for Springfield, ensuring it stays “bone-dry” until Homer surrenders the bear. In a surprising turn of events, a compassionate Burns allows Maggie to keep Bobo, offering her some wisdom: “Avoid making the same mistake I did.” This instance showcases an uncommon act of kindness from a character typically portrayed as malevolent. The Simpsons is a gracious series, enabling audiences to connect with numerous characters on an emotional level. In this case, Burns takes center stage.

49. “Bart of Darkness” (Season 6, 1994)

As the sweltering heat takes over Springfield, the Simpsons decide to splurge on a swimming pool, instantly elevating Bart and Lisa to the most admired kids in town. However, misfortune strikes when Bart injures himself (Nelson chuckles maliciously, Milhouse interjects with concern, “Hey Nelson, he’s genuinely hurt! I think he’s broken his leg.” Nelson responds callously, “I said ha-ha.”), leaving him confined to a cast for the remainder of the summer. With the pool off-limits, Bart retreats to his room, and in an attempt to fill the void, Lisa lends him her telescope. Through this lens, he witnesses one of our neighbors committing a heinous act.

A tribute to the film “Rear Window” – in this episode, Bart experiences two instances where he seems to be looking at an injured character (much like Jimmy Stewart) through his telescope. The stories in “Bart of Darkness” intertwine effectively. The pool story teaches Lisa (and poor Martin without pants) a lesson about the fleeting nature of popularity, while the Bart plot provides its own independent humor, such as the clever visual joke where Bart’s leg is in a trashcan and on a patch of grass. Additionally, there’s a scene where Bart calls a service similar to Moviefone that still manages to work on two levels even though Moviefone is no longer popular. But when you add the word “regicide” into the mix, it keeps being funny long after the reference has faded.

48. “Mayored to the Mob” (Season 10, 1998)

In the yearly “Two Month Science Fiction Convention,” Homer bravely rescues Mark Hamill from a horde of voracious fans by whisking him away. Mayor Quimby is moved by this act of bravery and recruits Homer as his personal bodyguard, an unusual match but one that seems to fit well here: They both are driven by their desires, whether it’s women (Quimby) or freebies (Homer). However, their bond almost crumbles when Homer discovers Quimby is partnering with Fat Tony to peddle rat “malk” to the kids of Springfield Elementary. Despite this, Homer decides to continue working alongside the mayor, but only on the condition that he’ll apprehend the mobster.

In a surprising turn of events, Quimby is the one who takes action, but Fat Tony manages to break free swiftly and plots to take revenge on the person who had him imprisoned. This plot twist unfolds during a dinner-theater performance of “Guys and Dolls,” featuring Mark Hamill. This creative link between the initial act and the final one gives “Mayored to the Mob” an impressive sense of conceptual unity, setting it apart from other episodes where Homer acquires a new job.

47. “Itchy & Scratchy Land” (Season 6, 1994)

Itchy & Scratchy World: A Place Where Nothing Could Potentially Go Right, Except for a Few Exceptions Like Killer Robots

The story begins smoothly, but the Simpson family trait eventually surfaces, leading Bart and Homer into trouble due to several misdeeds. A group of robots modeled after Itchy and Scratchy are poised for destruction. This episode abounds with film allusions such as Jurassic Park, Westworld, The Birds, and even Walt Disney, yet it also includes one of the series’ most memorable jokes: “No, my son is not called Homer, but Bort!

46. “Scenes From the Class Struggle in Springfield” (Season 7, 1996)

In this episode, it appears that our list of 100 may have underestimated Marge significantly, as we delve straight into her emotional struggles. On discovering a Chanel suit reduced from $2,800 to just $90, Marge becomes quite fond of it and starts wearing it frequently, even on trips like the one to the Kwik-E-Mart. Here, she bumps into an old high school friend, Evelyn, who is both wealthy and snobbish. Evelyn admires Marge’s unique style, and extends an invitation to the Simpson family to visit the Springfield Country Club, where they rub shoulders with the elite of society.

Marge yearns to fit in despite being an outsider at the exclusive country club, which seems filled with snobs and social climbers. She’s anxious about her appearance, fearing rejection if she doesn’t dress appropriately. However, thanks to a sponsorship from Evelyn, the Simpsons become members. While this is what Marge desired, it comes at a price – she becomes harsh with Lisa, and Homer comments bitterly that now they can see how unrefined they truly are. This sharp remark is one of the more poignant lines from the show’s early years.

45. “Bart the Daredevil” (Season 2, 1990)

In the eighth episode of the second season of “The Simpsons,” titled “Bart the Daredevil,” something shifted. This episode revolves around Bart being captivated by Captain Lance Murdoch, who resembles Evel Knievel, and attempting to perform stunts on his skateboard. This showcases Bart’s character as a modern-day Dennis the Menace, which resonated strongly with the nation that was soon to be infatuated with “Bartman.” Beyond this, the episode delves into the relationship between Homer and Bart, and the extraordinary measures Homer takes to impart a fatherly lesson.

The episode that Matt Groening fondly refers to as his favorite, titled “Bart the Daredevil,” is particularly renowned for a joke that significantly shaped its future. If you haven’t had the chance to watch this episode yet, I encourage you to do so before continuing here. In this episode, after preventing Bart from attempting a skateboard jump over Springfield Gorge, Homer inadvertently hurtles down the ramp himself. This incident doesn’t have a happy ending. Homer experiences an extended, comically violent fall. He is eventually rescued by helicopter and placed inside an ambulance, but unfortunately, the ambulance crashes into a tree immediately, causing his stretcher to roll out the back. Homer continues to tumble down the Gorge in the same painful manner. The blend of absurdity and repetition in this scene felt revolutionary, and it became one of the show’s distinctive traits, similar to the iconic Sideshow Bob vs. Rakes scenes from “Cape Feare.

44. “Homer to the Max” (Season 10, 1999)

During the fall television season, numerous new shows are introduced by networks. It wasn’t until Lisa explained, “Dad, the initial episode is essentially a pilot. Producers often tinker with shows, modifying characters, eliminating certain ones, and moving others to the sidelines,” that we understood many early episodes were unnecessary.

As a devoted fan, I’m right in the thick of TV’s midseason and there’s only one show that grabs my attention: Police Cops, starring none other than… yes, you guessed it, Homer Simpson! But this isn’t our regular ol’ Homer; he’s cool, composed, and not just a cop but a POLICE cop. For the next week, I find myself strutting around Springfield, basking in the unexpected fame, but alas, Cool Homer soon gets demoted to Bumbling Sidekick Homer in the following episode. His catchphrase? “Uh-oh, SpaghettiOs.

43. “Homer at the Bat” (Season 3, 1992)

Homer at the Bat” serves as a pivotal episode, airing towards the end of Season 3 (although it was actually written earlier and took longer to produce). Often considered the most surreal episode from the show’s early era (Seasons 1-4), it’s when Homer plays for the power plant’s softball team that things start off simply. However, chaos ensues when Mr. Burns hires nine real baseball players as reinforcements.

The song “Talkin’ Softball” by Terry Cashman, heard during the closing credits (a revised version of his 1981 hit “Talkin’ Baseball”), is one of the series’ most memorable features. It gained fame for its humorous listing of misfortunes that befell the talented players, which grew progressively absurd over time. From Roger Clemens believing he was a chicken to Ken Griffey Jr.’s sudden growth spurt and Ozzie Smith falling into an endless void, these misadventures added a unique quirkiness that became synonymous with the show following season five.

42. “El Viaje Misterioso de Nuestro Jomer” (Season 8, 1997)

In “The Mysterious Journey”, instead of eating a super hot chili grown deep within the jungle by the inmates of a Guatemalan insane asylum, Homer consumes a bowl of peyote. However, if you were to partake in the same psychedelic substance yourself, you’d have a similar experience – an inventive and beautifully illustrated episode unfolds, where Homer experiences hallucinations, including a talking coyote (voiced by Johnny Cash) and a distorted version of Marge without a face.

Beneath its vibrant and captivating exterior lies a poignant tale about Homer’s fear that Marge might not be his true soulmate due to a misunderstanding. This episode is like a beautiful gift wrapper hiding a heartfelt message inside. It also includes one of the series’ more melancholic (and somewhat whiny) lines from Homer, where he says, “I’m just a tiny, insignificant dot on an aging planet, circled by a distant, uncaring sun.

41. “Much Apu About Nothing” (Season 7, 1996)

The people of Springfield aren’t inherently cruel or malicious; they simply get worked up quickly and are prone to rioting. Despite their fear of bears wandering the streets, their joy often turns sour when their taxes increase to fund the Bear Patrol that ensures their safety. To shield himself from criticism, Mayor Quimby scapegoats illegal immigrants. Initially, Homer joins in this blame game, but his perspective shifts when he discovers Apu isn’t originally from their country and should not be living there. “Much Apu About Nothing” illustrates the consequences of letting ignorance guide us.

As a passionate admirer, I find myself vehemently opposing the idea of expelling foreigners from our nation, as I’m faced with an additional $5 monthly fee. However, when I grasp that this measure could potentially force my dear friend to depart, I fiercely challenge Proposition 24. Meanwhile, Apu tirelessly strives to remain here, even enduring a subpar education at my hands – a man who cherishes America more profoundly than a refreshing beer on a scorching Christmas morning ever could.

40. “Homer the Great” (Season 6, 1995)

In 2000, Patrick Stewart stated to the BBC that his appearances on “The Simpsons” and “Sesame Street” might be the most notable roles he performed in the United States. Indeed, this seems accurate.

Stewart infuses Number One, head of a secret society reminiscent of Freemasons, called the Stonecutters, with an undeniable authority. However, it’s eventually unveiled that Homer is the Chosen One, causing things to take a positive turn for him. Yet, as Lisa puts it, “You’re feeling spiritually empty because your newfound power has distanced you from other people.” In an attempt to do good in the world, Homer sets up a Stonecutters Daycare Center and engages in other uplifting activities. Unfortunately, his brothers soon tire of their leader’s new morality, causing them all to depart and create the No Homers’ Club. The episode “Homer the Great” revolves around Homer, showcasing his uncommon selflessness as he asks more of himself and others. By the end of the episode, he returns to the Simpsons, who are still the best family in town.

39. “Homer’s Phobia” (Season 8, 1997)

Frequently, particularly during later seasons, the show The Simpsons tackles contemporary issues with precision. Episodes like “Homer’s Phobia” and “Much Apu Nothing” are among the most notable examples. In “Homer’s Phobia,” the Simpson family develop a friendship with John (voiced brilliantly by John Waters), the proprietor of a kitschy trinket store. Initially, Homer, along with the rest of his family, takes a liking to John. However, when he discovers that John is gay, Homer becomes apprehensive. The remainder of the episode showcases Homer’s ineffective attempts to prevent Bart from adopting homosexuality, most notably by taking him to a highly stereotypical steel mill.

The success of the episode lies in Homer serving as an ideal scapegoat for satire. Homer isn’t politically savvy; rather, he reacts impulsively, often demonstrating a lack of intelligence. He overstates his incorrect views so dramatically that they expose the absurdity of those viewpoints, even subtly. It becomes more engaging when Homer eventually recognizes his mistakes. While it may seem evident today what stance the show is taking on gay rights, it’s crucial to remember the context and audience – many may have been experiencing their first exposure to the topic through the show at that time.

38. “The Book Job” (Season 23, 2011)

In ‘The Simpsons’, the series continues to be worth watching beyond season 20, as the plot of ‘The Book Job’ is exceptionally well-crafted. In this episode, Lisa is taken aback when she learns that her beloved children’s book author is a fraud – the woman on the cover is actually an actress, and the team behind the marketing concocted the book. This revelation becomes Homer and Bart’s latest get-rich-quick scheme, leading them to recruit Skinner, Patty, Moe, Frink, and even special guest-star Neil Gaiman to collaborate on the Ultimate Young Adult Novel.

The story titled “The Troll Twins of Underbridge Academy” is successful, but the publishing company refuses to release it unless they can find an author with a compelling backstory. This episode is filled with satire and pokes fun at various popular works such as the “Twilights” and “Ocean’s Eleven.” In this case, Andy García portrays the struggling publisher. The title “The Book Job” demonstrates that even after more than two decades, “The Simpsons” continues to be sharp and relevant.

37. “Homer’s Barbershop Quartet” (Season 5, 1993)

As early as 1993, it was challenging to find a fresh perspective on the Beatles. However, “Homer’s Barbershop Quartet,” where John, Paul, George, and Ringo are replaced by the Be Sharps (comprising Homer, Skinner, Wiggum, Barney, and Apu de Beaumarchais), while it heavily borrows from the Beatles’ origins and subsequent rise and fall, introduces one significant change: It goes bigger in scale.

Instead of John Lennon saying the Beatles were “more popular than Jesus,” the Be Sharps named their second album, Bigger Than Jesus. Instead of Homer putting down his dessert so he could be appropriately starstruck by George Harrison, he eats an endless stream of brownies. Instead of Ringo, something something Burt Ward? “Homer’s Barbershop Quartet” could have been a lazy parody of the world’s most famous band, but the writers were self-aware enough to sprinkle some welcome weirdness around the references.

36. “Lisa on Ice” (Season 6, 1994)

At its peak, “The Simpsons” skillfully combines tender emotions with uproarious chaos. For instance, the episode titled “Lisa on Ice” demonstrates this perfectly – it begins with dramatic explosions on Kent Brockman’s “Action News” and concludes with a heartwarming scene between Bart and Lisa, one of the show’s most touching moments. This story revolves around sibling rivalry, triggered by Lisa’s fear of failing gym class. (It’s also worth mentioning Ralph’s famous quote, “Me, fail English? That’s unpossible!”)

As Apu recognizes Lisa’s talent for being an exceptional goalie, she becomes part of his hockey team and quickly surpasses Bart. Homer’s inept parenting adds fuel to the fire, causing chaos when he turns on the lights and shouts “FIGHT! FIGHT! FIGHT!” upon discovering that Bart and Lisa will play against each other in a game. In the end, neither of them wins Homer’s approval as a deciding penalty shot leads to their realization that love overcomes all (even though it leaves everyone else in disarray due to the ensuing riot).

35. “That ’90s Show” (Season 19, 2008)

“The episode ‘That ’90s Episode’ from The Simpsons is a subject of debate among fans due to its departure from the established storyline. However, as demonstrated by this list, many controversial episodes turn out to be excellent because they dare to challenge our assumptions about the show. Reminiscent of a traditional sitcom flashback episode, ‘That ’90s Episode’ effectively satirizes the ’90s and offers valuable insights into Marge and Homer’s relationship by depicting how Marge attended college and became infatuated with one of her professors.

The episode presents a striking contrast by the witty irony that the one constant of the ’90s, “The Simpsons,” is absent: “That ’90s Episode.” This episode illustrates what popular culture might have been like without the series, filled with skepticism and arrogance. At the time, “The Simpsons” served as a comforting commentary for many. Some viewers criticize “That ’90s Episode” for overlooking the show’s history, but I believe there are few episodes more respectful of its legacy.

34. “Lisa’s First Word” (Season 4, 1992)

Lisa’s First Word” isn’t really a lengthy episode; it’s more like a treasure trove of memorable quotes. Just about every line from this season-four favorite, which mainly unfolds after Lisa is born, has become a catchphrase, ranging from the classic “I can’t sleep, clown will eat me” to the self-adoring “everybody loves me, I am so great” and the heartfelt “a baby and a free burger, could this be the best day of my life?” to the endearing “iron helps us play.” (Hey there, Joe!)

In my humble opinion, this heartwarming film revolves around the family’s quest to prompt their child, Maggie, to utter her first word. The scenes are filled with a sweetness and charm that outshine any nostalgic flashback episode from an animated series. Remarkably, even after twenty-two years, Maggie has only spoken one word – “daddy,” voiced by the legendary Elizabeth Taylor herself. Yet, it’s this solitary utterance that encapsulates the essence of their bond beautifully.

33. “King-Size Homer” (Season 7, 1995)

In “King-Size Homer,” our protagonist finally achieves all his lifelong desires, but then finds himself struggling to locate an essential item – the ‘ANY’ key, symbolizing his inability to find satisfaction or purpose in his new lifestyle. Essentially, Homer transforms into a precursor of modern bloggers by working from home due to his excessive weight gain, which is an unusual portrayal of pride associated with weight increase on television.

This episode employs an ingenious tactic: despite its theme of a father motivating his son to clean himself using a stick and rag, it’s remarkably vibrant. Homer finds it hard to stay put while working at home, and the climax features his thrilling ascent up the power plant tower to thwart a potential disaster reminiscent of Chernobyl. This is juxtaposed with Mr. Burns’ unexpectedly energetic “groove out, let love in” fitness class.

32. “Krusty Gets Kancelled” (Season 4, 1993)

Across Springfield and its broadcast channels, there’s been plenty of chatter about the enigmatic character Gabbo, who turns out to be a children’s television host – a ventriloquist’s dummy known for his outrageous behavior and catchphrase “I’m a bad widdle boy!”. This character manages to undermine Krusty’s popularity ratings, leading the network to cancel him. As Krusty grapples with despair, Bart, Lisa, and Luke Perry (playing himself) offer their support. In the end, the kids manage to defeat Gabbo by exposing him on a live feed that was intended to go off-air during commercial breaks – a tactic similar to the one used in 1957’s film ‘A Face in the Crowd’ to take down a reactive talk show host.

Krusty is at his funniest when he’s drowning in self-pity, and the episode “Krusty Gets Kancelled” offers him a huge pool to do just that. He ends up working at a fast-food joint, gains a lot of weight, and complains about his life constantly. (Krusty: “Yuck, 35 years in show business and already no one remembers me, just like that guy and the other one, you know, the one who always wore a shirt?” Bart: “Ed Sullivan?”) And similar to many episodes of The Simpsons, this one enjoys making fun of people being easily swayed by grand advertising schemes, with a hint of mind-control tactics. (“Gabbo! Gabbo! Gabbo!” flashes the enigmatic ads.)

31. “Homer vs. the Eighteenth Amendment” (Season 8, 1997)

The comedy in “The Simpsons” is layered, encompassing situational, character-specific, visual, auditory, and self-contained joke elements. When these components work together seamlessly at their best, it’s quite a spectacle to witness. An instance like this can be found in the episode where Prohibition is reintroduced in Springfield, leading Homer to become an underground brewer known as the Beer Baron, pursued by a character reminiscent of Elliot Ness named Rex Banner. This particular episode is well-known for its closing remark, which has stood the test of time (“To alcohol: the cause and the cure of all life’s problems.”), but “Homer vs. the 18th Amendment” is filled with witty lines throughout.

The voice acting in “The Simpsons,” particularly Dave Thomas’s portrayal of the humorless Banner, is so remarkably reminiscent of The Untouchables and Dragnet that it’s tough to envision the episode thriving without it. He even tells Marge, “Now wait just a moment, ma’am.” “It’s not for us to decide which rules we follow,” he continues. “If we could, I’d eliminate everyone who gave me a sideways glance!

30. “Lisa the Boy Scout” (Season 34, 2022)

In recent seasons, The Simpsons sometimes struggle with their own self-awareness, as they cannot ignore the cultural impact they’ve made over the years but can come off as defensive when directly addressing audience expectations. However, this is one of the show’s strengths – starting an episode with a false premise and eventually leading to an entirely unrelated main plot. This episode takes it a step further by initially focusing on Lisa joining the Boy Scouts, which triggers a competitive dynamic between her and Bart, but then swiftly shifts to a group of anarchist hackers infiltrating Disney’s servers to reveal “lost” Simpsons episodes that were buried due to their poor quality. This leads to a series of hilarious sketches featuring supporting characters like Martin, Groundskeeper Willie, and Professor Frink, while also offering sharp satire on various topics such as cryptocurrency enthusiasts, intellectual property acquisitions, and the annoying trend of people claiming The Simpsons predicted everything. In some cases, the Rick and Morty effect isn’t a bad thing at all.

29. “Homie the Clown” (Season 6, 1995)

In a twist of fate, Homer’s likeness to Krusty – sporting a bald pate and a doughy frame – becomes beneficial when he joins Krusty’s clown college and lands a job as a Krusty doppelganger. Lisa praises this development by saying, “If there had to be a clone of Krusty, I’m glad it’s you.” However, Homer’s performance is so authentic that he falls prey to the Springfield Mafia, who are seeking reimbursement for a debt that Krusty incurred when opening his clown college. (The opening scenes depict Krusty lighting a cigarette from an Action Comics #1.)

Among the series’ most hilarious episodes, this one stands out. The large-scale jokes are entertaining (the climax has Don telling Homer, “You’ve brought great joy to this old Italian stereotype!”), but the subtleties like Krusty’s furtive glances and expressions are even funnier. For instance, Krusty’s shifty-eyed look when Homer exclaims, “You came here to save me!” never fails to amuse. Homer endures a lot of hardship in his degrading tasks such as hosting kids’ parties, swap meets, and other insignificant chores that Krusty describes as “the kind I wouldn’t touch with a ten-foot clown pole.” Despite the dire situation, the fake Krusty never turns cruel like the original, nor as desperate as Dick Cavett (who played himself), who casually drops names as if he’s being compensated per anecdote. By the way, Krusty owes $48. He pays with a $50; the Don gives him change.

28. “HOMR” (Season 12, 2001)

A tribute to “Flowers for Algernon” that surpasses its original in humor and emotional depth is presented here. Rather than an intelligence-enhancing operation, the story revolves around Homer, who gains intellect when a deeply implanted crayon is extracted from his brain. As Homer comes to understand more about the world, he realizes how challenging and alienating life can be for intelligent individuals.

It’s a theme that runs through a series that is written by a bunch of Harvard nerds, but is especially well-articulated here. (The episode was written by Al Jean, one of the original Harvard nerds and showrunner for the past 13 seasons.) The episode’s ending is one of the series’ most poignant moments ever. When he got smarter, Homer and Lisa grew instantly closer, and when he decides to reverse the procedure and become dumb again, Homer first writes his daughter a note that is truly tear-jerking.

27. “Lisa vs. Malibu Stacy” (Season 5, 1994)

In the show “The Simpsons,” characters Lisa and Abe are often portrayed as dull or boring. However, an interesting episode demonstrates that they can be just as entertaining as Homer or Bart. The plot cleverly highlights Lisa’s strong activism and Abe’s bumbling old age, creating storylines where these traits become the focus.

Lisa’s fight against the sexist Malibu Stacy doll company may have hit a dead end when her rival was replaced by a last-minute hat upgrade, but it still marks one of the strongest feminist statements on the show. Meanwhile, Abe attempts to regain his youthfulness through a part-time fast-food job, only to find that he doesn’t want to be on the other side of the counter. In this case, Abe’s confusing monologues push people away, but they also make him stand out in many iconic episodes. While Lisa and Abe are known for their grumpiness, there is merit in being different.

26. “Bart on the Road” (Season 7, 1996)

The classic road trip episode is a long-standing tradition in sitcoms, similar to arranging simultaneous dates with two distinct women. However, “Bart on the Road” subverts this trope by abandoning the usual coming-of-age storyline and instead presenting an utterly preposterous scenario – a plot involving Nelson threatening to fight Bart, Milhouse, and Martin unless they attend an Andy Williams concert (“Bam, second encore!”). Moreover, it explores the notion that being an adult isn’t as glamorous as it’s often portrayed. Yes, you can watch Naked Lunch whenever you desire, but you might well question if there aren’t at least two things odd about that title.

Even Homer needs the imagination of Lisa, who’s sent to the power planet for Go to Work With Your Parents Day, to reveal the magic in the mundane — it’s amazing how easily radiation suits can make you feel like you’re an astronaut. Cherish your youth, “Bart on the Road” brilliantly suggests, because before too long, you’re working as a courier, hauling a cooler labeled “HUMAN EYES” through an airport in Hong Kong.

25. “I Love Lisa” (Season 4, 1993)

The exact moment audiences become smitten with “I Love Lisa” is unmistakable: It’s when Ralph, exasperated by Lisa’s frustration over his affections, grabs his chest in dismay as she angrily declares, “Hear me now, I don’t fancy you! I’ve never fancied you!” This pivotal scene takes viewers on a journey through the early stages of romance, encompassing infatuation, heartache, and ultimately, the heartwarming restoration of friendship.

That scene in “The Simpsons,” particularly the episode “I Love Lisa,” is not only remembered as one of its most significant moments, but the entire heartwarming narrative has left an indelible mark on viewers. The popular phrase “I Choo-Choo-Choose You” is undeniably one of the show’s most frequently repeated quotes.

24. “Homer’s Enemy” (Season 8, 1997)

“Did you really go into outer space? Really?” translates to “Were you actually in space? Is that true?

In contrast to the self-made man character Frank Grimes, who debuts as the latest employee at the plant in “Homer’s Enemy,” he doesn’t have a lavish lifestyle. Instead, he lives in a small room above a bowling alley and beneath another one. Remarkably, he manages to avoid going insane under these conditions, but his encounter with Homer is like a crumbling factory, partly due to jealousy but mainly because he can’t fathom how one man could live such a fortunate life without much effort. This episode has a unique tone and humor that differs from any preceding one, and no other episodes have matched its dark wit since. Despite the fact that Grimes essentially commits suicide due to Homer, it’s hard not to feel affectionately towards him because of his innocent, sweet, and somewhat foolish nature.

23. “Secrets of a Successful Marriage” (Season 5, 1994)

In a fresh turn of events, Homer now holds the position of an adult educator, teaching a class named after this very storyline. However, what was meant to be secret classroom material, unfortunately, reveals some underlying marital issues and intimate aspects of Homer and Marge’s relationship. Matters become more complicated, leading to Homer’s expulsion. In a peculiar twist, he forms a union with a plant, only to then make an earnest attempt at rekindling his relationship with his human spouse.

This episode is a clear demonstration of the show’s skill at cramming numerous elements into just 22 minutes. It’s not only filled with well-known jokes, such as Homer’s rapid-fire quotes mimicking Jack Nicholson, but also in the narrative itself. The story begins by focusing on Homer’s slow-wittedness, then takes us on a tour of various adult education classes, including Moe teaching “Funk Dancing for Self-Defense”. It evolves further with Homer becoming a teacher, followed by Marge kicking him out, leading to his insanity, homelessness, and becoming as filthy as a typical Frenchman. Each of these stories could have sustained an entire show on its own, but The Simpsons masterfully combines them all smoothly.

22. “Simpsons Roasting on an Open Fire” (Season 1, 1989)

The story kicks off here, as Bart required a tattoo removal and depleted the family’s savings, while Homer missed out on his Christmas bonus and had to save the holiday celebrations. This episode not only marked its debut but also set the stage for a common type of Simpsons storyline: an instance where Homer switches jobs, in this scenario taking up the role as a mall Santa.

Although ‘Simpsons Roasting on an Open Fire’ was the first episode aired during the Christmas special, it wasn’t the very first episode produced. In fact, it was the eighth one. This doesn’t diminish the quality of the episode in any way. On the contrary, it is a superior episode compared to the following seven episodes that struggled to establish the show’s tone and pace. The characters in those early episodes were still finding their footing. With its unique blend of intellectual humor and emotional depth, ‘Simpsons Roasting on an Open Fire’ feels remarkably complete. A subtle joke at the end of the episode, where Homer brings home a dog as a Christmas surprise for the family, showcases the essence of The Simpsons so perfectly that it could have fit seamlessly in any subsequent season.

21. “The City of New York vs. Homer” (Season 9, 1997)

When Homer discovers his vehicle is unlawfully impounded in New York City, the Simpson family chooses to make a joint journey there. However, there’s a snag: Homer detests New York City. As he struggles to free the boot from his car, which only solidifies his dislike of the city, the rest of the family appears to enjoy their trip. This episode was always popular among viewers. Unfortunately, following the 9/11 attacks, it was removed from syndication.

Initially, the decision appeared logical given a significant portion of the episode unfolded at the World Trade Center. However, it sparked debate among fans, particularly those from New York, because in many aspects, the episode was a tribute to the city, showcasing both its incredible and incredibly challenging aspects through the series’ exaggerations. Scenes like Homer attempting to remove his car boot by chewing off one of the bolts are rarely matched in their portrayal of NYC on television or film. In one scene, a man from one of the towers quips, “After you finish that, I’ve got something up here for you to bite on.” Another man then scolds the first, saying, “Why don’t you be polite, you filthy cur!” before offering Homer assistance, all while maintaining the distinctive New York accent and combative demeanor.

20. “Radioactive Man” (Season 7, 1995)

The much-anticipated live-action film adaptation of “Radioactive Man” is set to be filmed in Springfield during springtime, with Rainier Wolfcastle playing the lead character. Bart attempts to secure the part of Fallout Boy, the hero’s sidekick, but ultimately loses out to Milhouse due to his slight height advantage. However, Milhouse remains discontented in the role as he had only accepted it to please his greedy parents.

One unforgettable episode from “The Simpsons” – and this is quite a claim – is “Radioactive Man.” This episode brilliantly combines several recurring themes in the show, such as rivalry among friends, fascination with comic books, changing pop culture trends (as seen when the old Radioactive Man series mirrors the 1960s Batman starring Adam West), and the distortion of innocence, as Moe reminisces about his difficult days as a Little Rascal known as “Smelly.” This episode also propelled Rainier Wolfcastle, a regular guest star, into stardom. He delivers the hero’s iconic phrase “Up and atom!” with a unique twist, saying “Up and at dem,” and reacts to an incoming tidal wave of acid with a deadpan, “My eyes… they do nothing!

19. “Holidays of Future Passed” (Season 23, 2011)

Originally, “Holidays of Future Passed” was penned as a potential finale for The Simpsons, should contract negotiations with the cast not succeed. This is evident in its tone, which looks back wistfully at the past, focusing on Bart and Lisa’s struggles with parenthood as a reflection of their relationships with their own parents. Furthermore, by placing it in the future, the episode allows for a variety of absurd scenes, such as Bart’s treehouse tree coming to life and expressing its resentment.

Discussing the treehouse, it’s where Bart and Lisa, both grown up and slightly intoxicated, have a profound, mature talk about their mutual respect and unique bond, having lived in the same house. This is one of the most emotionally stirring scenes from the entire series (with 25 seasons to consider), largely due to Bart’s sincerity enforced by a court-ordered chip. The episode “Holidays of Future Passed” truly showcases the show at its peak performance, offering heart, satire, absurdity, and witty one-liners in a way that only the best episodes of The Simpsons can, making it feel like more than just a great TV episode; it’s a testament to something extraordinary. If this had been the finale, it would have been a fitting conclusion.

18. “You Only Move Twice” (Season 8, 1996)

In a playful imitation of James Bond, particularly the film “You Only Live Twice,” this story takes an outrageously humorous turn, concocting global events that are soon to be overshadowed by next week’s news. Homer secures employment at the enigmatic Globex Corporation, helmed by a hidden villain, Hank Scorpio, who surprisingly appreciates Homer. However, his family – Marge and the kids – find life in Cypress Creek unpleasant and yearn to return to Springfield. A disagreement over this arises between Homer and his employer, but is abruptly halted when government forces assault Scorpio’s headquarters. The absurdity only escalates from there.

In a humorous take reminiscent of Mel Brooks’ middle-era comedies, “You Only Move Twice” is a comical spin on Bond themes. The titular character himself appears and experiences a Goldfinger-like ordeal, rechristened as “James Bont.” Albert Brooks, a frequent Simpsons guest star, voices Scorpio, a character who sounds like an Albert Brooks creation – talkative, self-promoting, and always boasting about his ideas. In the scene, Marge expresses her amazement at their luxurious house, to which Scorpio replies, “We don’t have homeless people in our town, Marge, and if we did, they wouldn’t be rushed. They’d be allowed to go at their own pace.” The villainous menace of Bond films is humorously portrayed here. For instance, Scorpio asks Homer about his preference between France and Italy, then fires a missile at his second choice, France, saying, “Nobody ever says Italy.

17. “22 Short Films About Springfield” (Season 7, 1996)

This episode of “The Simpsons” is remarkably innovative, drawing inspiration from movies like “32 Short Films About Glenn Gould“, “Pulp Fiction“, and the free-flowing works of directors such as Robert Altman and Richard Linklater. It’s a collection of short stories or vignettes, not tied together by a conventional plot, but rather by common themes. At times, it also employs unconventional filmmaking techniques in its transitions, making them particularly clever.

Additionally, there’s the unforgettable moment when Principal Skinner extends an invitation to Superintendent Chalmers for dinner at his home, only to botch it up by serving him Krusty Burgers disguised as “steamed hams.” This blunder would surely win the approval of the Marx Brothers.

16. “Lisa’s Sax” (Season 9, 1997)

Following Bart’s impulsive action of throwing his saxophone out the window, Lisa feels deeply saddened. She expresses that she can hardly recall her life before it, which surprises Homer and Marge enough to share the story of how the instrument came into their possession. According to them, this event transpired in 1990. At the time, Bart was unhappy at kindergarten, Lisa was yearning for mental stimulation, and Homer and Marge were saving up $200 for an air conditioner. It wasn’t until a small Lisa walked past a music store that things took a turn. Homer prayed for guidance, and lo and behold, a sign appeared in the window: “Musical instruments: the key to nurturing a gifted child.” They ventured inside and left with a saxophone.

Each character reveals their authentic essence beautifully: Homer may seem dim-witted, yet he’s profoundly devoted; Marge provides a balanced perspective without being overly rigid; Bart exhibits mischief and naughtiness as a search for validation and friendship; Lisa experiences a sense of underappreciation but learns about her parents’ deep affection. The baby versions of Lisa, Bart, and especially Milhouse are an added delight!

15. “A Milhouse Divided” (Season 8, 1996)

As a passionate film lover, I decided to shake off one of my creative dips by hosting a grand gathering at the Simpsons’ abode, inviting esteemed guests such as the Flanderses, Hibberts, Lovejoys, and Van Houtens. However, the harmonious atmosphere was abruptly disrupted when Milhouse’s parents found themselves embroiled in a heated argument, deepening the cracks that eventually led to their divorce.

Title “A Milhouse Divided” effectively accomplishes The Simpsons’ unique knack for exploring intensely raw, real-life issues with just enough humor to prevent discomfort. At its heart lies the depiction of people neglecting or misinterpreting their partners’ distress until it’s too late. The episode concludes with one of Homer’s characteristic brilliant-yet-foolish last-ditch attempts, this time secretly divorcing Marge to propose anew and redo their lackluster wedding, as shown in flashback when they ate a Carvel cake at a truck stop instead of having a formal reception.

14. “Home Sweet Homediddly-Dum-Doodily” (Season 7, 1995)

This episode of The Simpsons, for the first time in a more authentic manner, delved into the chaotic household life of the kids. Homer and Marge go on a spa retreat, leaving Bart, Lisa, and Maggie with Grandpa Abe. His care proves to be disastrous, leading Child Protective Services to remove them from the house and place them with the Flanders as foster parents. The Simpsons are told they can only get their children back after completing a parenting class. Bart resents the Flanders’ religious fervor and strictness, while Lisa finds comfort in their structured lifestyle.

The whimsical and heartfelt phrase ‘Home Sweet Homediddly-Dum-Doodily’ encapsulates many beloved episodes with its blend of emotion and humor. This specific episode carries an undertone of fear tempered by absurdity, as seen when Lisa and Bart return home from school, the former barefoot due to bullies and the latter wrapped in a burlap sack after his clothes were burned to prevent lice. Although amusing, this situation is distressing because the children are genuinely upset. Ultimately, we hope for Marge and Homer’s successful reunion with their kids, not just because the Flanders overstep boundaries by attempting to baptize them in a suspenseful scene that could be offensive, but also because the climactic joke—Homer reacting to the baptism water like a vampire—implies that, in a way, God is on the side of the righteous.

13. “A Streetcar Named Marge” (Season 4, 1992)

Everyone remembers the A plot of this one — Marge somehow wins the role of Blanche DuBois in a community-theater production of a musical version of A Streetcar Named Desire, written and directed by Llewlyn Sinclair (guest-star Jon Lovitz) — and deservedly so. But the B plot, which finds Maggie getting socked away in day care and plotting a prison-movie-style escape, is just as strong, sweet, and funny.

This episode of the show was especially dedicated to its writers and musical director, Alf Clausen. The nursery room scenes featured a rearrangement of Elmer Bernstein’s music from The Great Escape. Among the catchy yet absurd tunes in the musical were “You Can Always Depend on the Kindness of Strangers” and “New Orleans.” The latter’s lyrics, which painted a hyperbolic picture of New Orleans as “stinking, rotten, vomity, vile,” stirred up controversy in the city. In response to the outcry, the series issued an apology the following week by having Bart write “I will not defame New Orleans” on the chalkboard that appeared during the opening credits.

12. “Behind the Laughter” (Season 11, 2000)

Despite typically being more relaxed about continuity than many TV series, “Behind the Laughter” surpassed expectations. Mimicking the VH1 show Behind the Music, it’s a tale of rise and fall that appears to unfold not within the Simpsons universe, but parallel to it. It shares a level of self-awareness with “The Itchy & Scratchy & Poochie Show,” although in a distinct manner.

It seems that the family behind this show initially made their break by creating a pilot which ultimately led to its current success. However, they faced internal disputes over finances, broke up, struggled financially, and eventually reunited at the Iowa State Fair. The show is filled with subtle references (some requiring insider knowledge like the Simpsons posters promoting real shows), while others are more universally understood (such as when Bart gets fired for attacking flight attendants and is replaced by Richie Rich). The show also offers a relatable portrayal of the challenges faced in the entertainment industry; Homer becomes dependent on painkillers, Marge loses a significant amount of their wealth through poor investments, and Lisa eventually writes a memoir titled “Where Are My Residuals?”.

11. “Summer of 4 Ft. 2” (Season 7, 1996)

On the dismal last day of school – one of many alike in this time and place-shifting scenario – Lisa feels hollow when no one takes the time to sign her yearbook. Overwhelmed by feelings of unpopularity, she decides to transform herself during a family trip to a coastal town, adding an empty suitcase to the mix for dramatic effect. Her new identity becomes a carefree, popular “cool” girl, distancing herself from her intellectual self.

Similar to many episodes focusing on Lisa, this one delves deep into the challenges faced by a young girl as she tries to shape her own identity truthfully. This might be why it contains fewer big laughs compared to other episodes, but it still includes some subtle humor, such as when Lisa sadly looks at a photo of Gore Vidal and laments that he’s “kissed more boys than I ever will.” Her mother responds with, “Girls, Lisa. Boys kiss girls.

10. “Bart’s Birthday” (Season 35, 2024)

After years decades of speculation, The Simpsons finally airs its series finale. As it is a finale, there are a variety of conclusory, spinoff-establishing notes: Comic Book Guy becomes a father, Moe closes Moe’s, Chief Wiggum moves towns to lead the Chicago Police Department’s All Decapitation Unit. Most shockingly, Bart is finally aging and inviting people to his 11th birthday party. Except, of course, not. It was all a Bart-esque prank, inspired by Renaissance-era showrunner Matt Selman’s frustration with constantly being asked in interviews when the show would end and what would a series finale be. To be specific, “Bart’s Birthday” starts as an event hosted by Conan O’Brien celebrating the show airing its finale, which O’Brien explains was generated by an artificial intelligence. As a result, the episode within the episode is filled with series-finale clichés (every scene ends with a character leaving a room, turning off a light, and saying, “I’m going to miss this place”). “Bart’s Birthday” is in the style of a series finale, parodying series finales, commenting upon why The Simpsons was designed not to ever have a finale, but it aired as the season premiere.

Bart’s Birthday” stands out as the most daring episode in the history of daring episodes on The Simpsons. It manages to feel fresh yet true to the show’s character, employing its unique blend of respect and disrespect for TV conventions and its own legacy. With a James L. Brooks-esque emotional depth that is sincere yet immune to sentimentality, it pushes the boundaries of television storytelling, demonstrating what can be achieved in an episode and how a tale can be crafted. The recent Simpsons renaissance, marked by bolder moves, lofty ideas, playful trolling, disregard for established lore, and a reevaluation or even deconstruction of characters, is at its peak in this modern masterpiece. This episode will forever remain a perfect 10, just like Bart himself.

9. “A Star Is Burns” (Season 6, 1995)

In the series, “A Star Is Burns” is one of the few episodes that blend elements from different shows, specifically with “The Critic,” a short-lived series produced by Al Jean and Mike Reiss from The Simpsons team. This show was moved to Fox after it was canceled on ABC. However, any discomfort arising from the fusion of creative minds fades away when Jay Sherman, the critic character played by Jon Lovitz, arrives in Springfield for its first-ever film festival.

In this episode of “The Simpsons,” you’ll find yourself laughing and feeling uncomfortable due to its sharp critique of Springfield’s insensitivity, even as it uses it for humor. It also serves as a witty satire of almost every film festival imaginable, exposing the creators’ mindsets in sometimes unfavorable ways. For instance, Bart submits cruel hidden-camera footage of his father struggling to fit into tight pants, Ned Flanders creates an amateurish movie about Moses that sends one of his children drifting down a river, and Hans Moleman’s “Man Getting Hit in the Groin by Football” speaks for itself. As usual, Barney demonstrates hidden sophistication with his black-and-white psychodrama about alcoholism, but Homer, who’s on the judging panel, prefers the one with the football to the groin. In the end, Barney wins, but Homer is correct in a way: Hans Moleman’s short film is later remade with George C. Scott and earns an Oscar.

8. “Deep Space Homer” (Season 5, 1994)

To generate excitement about their space program, NASA selects an everyday person, specifically Homer Simpson, to join astronauts Race Banyon and Buzz Aldrin from Apollo 11 on a mission. This move presents the writers of “The Simpsons” with countless opportunities for science-fiction humor. The training phase necessitates Homer’s fellow crew member Barney to abstain from alcohol, revealing his hidden talents as a gymnast and opera singer (he sings two lines from the Major General’s song in “The Pirates of Penzance”; reminiscent of “Cape Feare”). Homer’s apprehensions about space travel become a reality when he opens a bag of smuggled potato chips in zero gravity, causing an incident similar to Apollo 1.

From beginning to end, “Deep Space Homer” is a delightfully absurd spectacle, primarily serving as a platform to highlight Homer’s foolishness, clumsiness, greed, cowardice, and seemingly endless good fortune. It’s a timeless classic, filled with hilarious spoof moments. For instance, the scene where Homer munches chips zero-gravity style to “The Blue Danube” stands out as one of the best tributes to Stanley Kubrick in The Simpsons. The show’s knack for casually surreal details is also evident, as is the case when an inanimate carbon rod steals Homer’s space hero glory, winning him a ticker-tape parade and a magazine cover that reads “In Rod We Trust.

7. “Lisa the Vegetarian” (Season 7, 1995)

After caring for a lamb at a petting zoo, Lisa chooses to stop eating meat; however, everyone in town, even her own family, teases or resists her change. “What’s the distinction between this lamb and the one I cuddled?” Lisa questions her family, pushing her dinner plate aside. “This one was cooked for two hours in the oven!” Homer retorts. Yet, she stands firm in her convictions. The episode “Lisa the Vegetarian” on The Simpsons has a clear and undeniable political message, with Lisa continuing to be a vegetarian throughout the series.

6. “Treehouse of Horror V” (Season 6, 1994)

Among the outstanding “Treehouse of Horror V” episodes from The Simpsons’ annual Halloween series, this one cleverly references “The Shining,” time travel tales, and Soylent Green. It also features a condensed library of pop-culture humor and intensely violent visual gags as expected.

In “The Shining,” I find myself residing in Mr. Burns’s mansion during his absence, only for his decision to restrict Homer’s TV and beer causes a Jack Torrance-like descent into madness, allowing Dan Castellanata and the animators to deliver an outstanding performance as a hambone-mode Homer emulating Jack Nicholson. In “Time and Punishment,” a mishap while repairing a toaster turns out to be a time machine, resulting in rapid succession of jokes about time travel logic, many referencing Ray Bradbury’s short story “A Sound of Thunder.” One alternate reality I stumble upon delights me as it means my dreaded sisters-in-law Patty and Selma are deceased, but the world lacks doughnuts. The third installment, “Nightmare Cafeteria,” unveils that the subpar meat served by Lunchlady Doris is actually made from children ground up in a giant blender. The unexpected finale, where our family becomes distorted by a creepy blue fog (inspired by an old-time radio episode), is the most grotesque touch; it’s said that producer David Mirkin intentionally increased the violence in this one following network feedback suggesting the previous Treehouses were too gruesome.

5. “Lisa’s Substitute” (Season 2, 1991)

In place of Miss Hoover, who falls ill with Lyme disease, a temporary teacher named Mr. Bergstrom (played by Dustin Hoffman) takes over. He’s a kind, humorous man who enjoys playing the guitar and is well-liked by everyone. This new instructor seems to fulfill emotional needs that Lisa’s father, who can be rough and unsupportive of intellectual pursuits, doesn’t satisfy. Consequently, Lisa finds herself drawn to Mr. Bergstrom, her feelings largely stemming from his compassionate nature and shared love for learning.

Approaching towards the end of Season 2, “Lisa’s Substitute” stands out as one of the most heartwarming early episodes of The Simpsons. Despite incorporating its usual dose of pop-culture references, such as Miss Krabappel attempting to woo Mr. Bergstrom in a manner reminiscent of Anne Bancroft’s character in The Graduate, it predominantly operates in a “sweet” tone. What makes this episode unusual is its reserved nature, and the final sequence, where Homer acknowledges his shortcomings as a father and tries to connect with Lisa, is genuinely moving. Additionally, this is the first regular Simpsons episode to abbreviate its opening credits and immediately follow with the couch gag (in this instance, a repetition of the one from Season 2’s “Itchy and Scratchy and Marge,” where the family enters the living room only to find the couch missing).

4. “The Itchy & Scratchy & Poochie Show” (Season 8, 1997)

When Krusty the Clown complains that the fatigue of Itchy and Scratchy is causing his ratings to drop, the producers attempt to breathe new life into the violent cartoon by introducing a fresh character named Poochie. This canine character is portrayed as a surfer and rapper who lives on the edge, a product of network interference and brainstorming sessions with children who may not fully understand their own preferences.

In the realm of television, I found an exceptionally self-reflective episode of “The Itchy and Scratchie and Poochie Show,” a series already known for its insightful introspection, comparable to T.S. Eliot’s “The Waste Land.” This episode seems to anticipate and address criticism as it unfolds, making traditional critique somewhat redundant. It’s a veiled critique of commercial influence on art, with the character voiced by Homer ultimately sabotaging his own role by offering unwise suggestions. However, this harsh commentary is softened by the endearing characters of Lisa and Bart, who remind us that even the most beloved shows can become monotonous if they stay too long in the limelight, and that we should appreciate the free entertainment provided to us by their creators. (“Worst episode ever,” the Comic Book Guy repeats, unfazed.) Poochie’s short-lived career ends tragically yet comically: Homer’s voiceover is replaced mid-episode by another actor, and we witness animators physically tearing away the animation cel bearing the problematic pooch. The episode concludes with a surprising twist, as a teenager named Roy, resembling Poochie, mysteriously appears in the Simpsons household, adopting a Fonzie-like behavior towards Homer and eventually announcing his move to an apartment with two “very sexy” women.

3. “Marge vs. the Monorail” (Season 4, 1993)

Over and over again, this episode serves as a prime example of Springfield’s naivety when it comes to public works projects. The legendary Phil Hartman makes a guest appearance as con artist Lyle Lanley, who successfully convinces the townsfolk to invest their windfall in a monorail system. This tale will undoubtedly be referenced again and again whenever similar situations arise.

In the spirit of blending pop culture spoofs and biting social commentary, reminiscent of “The Simpsons,” the episode “Marge vs. the Monorail” abounds with memorable quotes and unforgettable scenes that verge on the surreal. At a town gathering, Lanyard makes his entrance dressed as Professor Harold Hill, leading the crowd in a song-and-response number akin to “The Music Man’s” “(Ya Got) Trouble,” with lines like “Are you here from the devil?” “No, good sir, I’m on the up and up!

2. “Last Exit to Springfield” (Season 4, 1993)

Lisa’s requirement for braces happens at the same time as Mr. Burns’s efforts to eliminate the nuclear power plant union’s dental coverage. Homer decides to run for union president and manages to win; Burns, who always tries to exert too much control, is portrayed as the villain he truly is, while mistaking Homer’s simplicity for strategic genius.

In simpler terms, this episode is another masterfully constructed one, gradually leading to a hilarious Dr. Seuss-inspired storyline where Burns becomes the Grinch, cutting off Springfield’s power, while the workers on strike, encouraged by Lisa playing like Woody Guthrie, act as the Whos from Whoville. Throughout, the episode includes some of the show’s funniest aside jokes (such as Homer’s predecessor mysteriously disappearing like Jimmy Hoffa, Lisa’s anesthesia fantasy reminiscent of Yellow Submarine, and a sequence showing what happens when Burns and Smithers replace the strikers with robots).

1. “Cape Feare” (Season 5, 1993)

In a nearly flawless half-hour of TV, the episode “Cape Feare” brings back Sideshow Bob, the large-footed maniac (portrayed by Kelsey Grammer), from prison and sends him to Springfield on a quest for vengeance, complete with musical interludes. While it’s a humorous take on the thriller Cape Fear (specifically, the 1991 Martin Scorsese remake rather than the 1962 J. Lee Thompson original), it follows the film’s structure closely, giving the episode an exciting momentum that’s rare for this show known for its digressions.

Although the episode is filled with terrifying moments reminiscent of films like Psycho, A Nightmare on Elm Street, and Cape Fear, causing the family to seek protection in a houseboat on Terror Lake and reenacting the show’s opening credits as “The Thompsons,” it manages to accommodate numerous, delightful visual jokes and dialogues. Ranging from Mel Brooks-esque humor (Sideshow Bob telling the parole board that his tattoo saying “Die, Bart, Die” is actually German for “The Bart, the”) to subtle jokes (Bob’s Night of the Hunter-inspired tattoos read “luv” and “hat,” as Simpsons characters only have four fingers), to ones that border on anti-humor (Bob repeatedly stepping on rakes), there is a wide variety. By the end, with Bart delaying the climax by persuading the vain Bob to perform the entire score of Gilbert & Sullivan’s “H.M.S. Pinafore,” the episode transcends into the realm of the extraordinary. Anne Washburn’s 2013 experimental play Mr. Burns imagines a post-apocalyptic world where the plot of Cape Fear is passed down with great reverence, as if it were Oedipus Rex or the story of Cain and Abel. This sounds quite believable to us.

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2024-12-17 22:05