20 Essential Episodes of It’s Always Sunny in Philadelphia

Originally released in 2022, the list now includes an additional episode as the gang from It’s Always Sunny in Philadelphia returns for their seventeenth season.

Among the numerous peculiar TV series, none quite match the charm of “It’s Always Sunny in Philadelphia.” This mostly plotless, vulgar sitcom revolves around a gang of unconventional bartenders, portrayed by a group of initially lesser-known actors (alongside Danny DeVito), who have been gracing our screens for almost as long as “Grey’s Anatomy.” Frankly, it seems improbable that such a show could thrive. Yet, against all odds, it does exist, and we are immensely grateful because “Sunny” is not just surviving but shining – it’s funnier, wittier, and more consistently surprising than most of its comedic counterparts.

Regarding the last section: Starting tonight, July 9, on FXX (with new episodes) and Hulu the next day, Sunny continues to surprise its audience with its audaciousness, much like in season one when the gang engaged in activities ranging from picketing abortion clinics to dating high-schoolers (they were 18!). The writers skillfully provide one surprising “I can’t believe they did that!” moment after another while preserving a relaxed, leisurely rhythm that mirrors Dennis’s comfort behind the bar.

It’s important to note that not all of Sunny’s 162 episodes have been successful; longtime fans are aware that several installments have fallen flat due to awkward jokes or misguided social commentary. Yet, loving Sunny means understanding and accepting its occasional shortcomings, as there’s always a trip to the Jersey Shore or a performance of “The Nightman Cometh” just waiting in the wings.

If you’re eager to relive some standout moments from the beloved series “Sunny” (or if you’re new here, welcome aboard! Get ready for the ride), we’ve compiled a list of must-watch episodes from this endearing little show before its 17th season kicks off.

“Charlie Gets Crippled” (Season 2, Episode 1)

In my opinion, the first season of the show Sunny isn’t its strongest. Don’t get me wrong, there are some memorable scenes, but overall, it’s too awkward and harsh to be genuinely funny. It’s not until Season 2 that Sunny truly becomes what fans recognize – when Frank (DeVito) enters the picture with a bang of blackmailing and vulgarity, forming the show’s well-known quintet. Even without Frank’s introduction, the episode is still quite enjoyable as Charlie (Charlie Day) exploits his so-called “disability” (Dennis ran him over with his car) to get special treatment at the mall, and Tiffany Haddish makes a brief, easy-to-miss appearance as a dancer.

“Dennis and Dee Go on Welfare” (Season 2, Episode 3)

One of Sunny’s standout features is its long-running jokes, which appear just frequently enough to elicit hearty laughter without becoming overly repetitive. For instance, consider Dennis (Glenn Howerton) and Dee’s (Kaitlin Olson) brief foray into crack addiction, an event confined to a single episode in season two but with repercussions that linger across subsequent seasons. Although it brought about significant disruption in their lives, lasting only a few days, it seems trivial in comparison to the long-term effects they experienced.

“Sweet Dee’s Dating a Retarded Person” (Season 3, Episode 9)

Absolutely, the title might seem outdated, but if you’re willing to look past that, this episode stands as a peak of early “It’s Always Sunny in Philadelphia.” The humor lies in Dee’s persistent denial about her boyfriend’s mental disability, which becomes funnier as she comes up with more absurd reasons. However, what truly makes this installment noteworthy is the introduction of “The Nightman,” a song by Charlie about a nocturnal creature that doesn’t molest him, and which would reappear in the subsequent season for one of “It’s Always Sunny in Philadelphia’s” best episodes.

“The Gang Solves the Gas Crisis” (Season 4, Episode 2)

In “The Gas Crisis,” Mac, Dennis, and Charlie endeavor to peddle gasoline, while a resentful Dee and Frank persistently claim her father is a terrorist due to his distribution of inheritance funds. The structure of this episode is robust, but a review by Rolling Stone eloquently explains why it’s crucial in the series It’s Always Sunny in Philadelphia: “This episode encapsulates the characters’ typical roles whenever they undertake an adventure akin to the A-Team, Ghostbusters, or Ocean’s 11. Mac (Rob McElhenney) is the brains, which is alarming in itself; Frank serves as the muscle; Dennis is the handsome one; Dee is the underachiever; and Charlie is the unpredictable factor.

“Sweet Dee Has a Heart Attack” (Season 4, Episode 10)

In this episode, Dee and Dennis trying to improve their health after a heart attack of Dee’s provides plenty of entertainment, along with a nod to DeVito’s “One Flew Over the Cuckoo’s Nest.” However, it’s Charlie’s wild, paranoid outburst that makes this episode a must-watch. It showcases the peculiar, unpredictable side of “Sunny” and even inspired a memorable meme that has been used by fans and non-fans for years afterward.

“The Nightman Cometh” (Season 4, Episode 13)

https://youtube.com/watch?v=watch?v=VCvr6tzZPTU

Among the musical episodes in “Sunny,” none has left as lasting an impression as “The Nightman Cometh.” It’s not just because it’s unique, but because of its brilliantly off-key elements that somehow manage to be perfectly imperfect. From the unforgettable tunes to the intricate sets, and let’s not forget Dennis’s Dayman codpiece, it’s a spectacle that’s so hilariously out of whack yet so captivatingly spot-on that we even took it on a mini cross-country tour.

“The Gang Hits the Road” (Season 5, Episode 2)

In the series, Sunny’s characters inflict such extensive destruction within the show’s main city that episodes set elsewhere are noticeable, including when they barely venture beyond the car. However, “The Gang Hits the Road” is unique because it’s the first time Charlie departs from Philadelphia, a significant milestone for the character and a source of numerous jokes not only in this episode but also throughout the series.

“The D.E.N.N.I.S. System” (Season 5, Episode 10)

Among all of Sunny’s romantic interests, Dennis stands out as the most challenging to embrace affectionately. At best, he exhibits narcissistic behavior; at worst, he is a suspected sexual predator who perceives himself as divine among women. The episode “The D.E.N.N.I.S. System” offers an unsettling glimpse into this intricate complexity, revealing the meticulous strategy behind his manipulative advances. It’s uncomfortable to witness, but it provides valuable insight into his character.

“Mac’s Big Break” (Season 6, Episode 4)

A significant aspect that keeps viewers captivated by Sunny is its knack for utilizing an array of unique, eccentric characters, whose complex personalities are intriguing enough to merit standalone stories. In the episode “Mac’s Big Break,” various cherished secondary personas (Rickety Cricket, Ben the Soldier, the Waitress) get their chance to shine, offering a delightful revisit of Sunny‘s exceptional talent for crafting rich and immersive settings.

“The Gang Goes to the Jersey Shore” (Season 7, Episode 2)

One standout episode for Sunny occurs at the Jersey Shore, but contrary to Dee and Dennis’ misguided idea to revisit their past, things turn out quite differently. Instead, events unfold around PCP, vomit, and “rum ham” – a notorious Sunny concoction that continues to be one of the show’s enduring jokes.

“Chardee MacDennis: The Game of Games” (Season 7, Episode 7)

https://youtube.com/watch?v=watch?v=QYGzf02qe3c

In a kennel, Frank resides. Dennis tosses beer bottles. Mac and Charlie’s game pieces are reduced to rubble by the triumphant, vengeful winners of their chaotic game, “Chardee MacDennis.” This episode of It’s Always Sunny in Philadelphia is undoubtedly one of its funniest, serving as a testament to the sheer enjoyment derived when the gang, and us viewers, decide to stay put at the bar instead of venturing elsewhere.

“The Gang Gets Analyzed” (Season 8, Episode 5)

As a film enthusiast, I must say that what truly sets this exceptional episode apart is the length it took for Sunny to finally have its flawed characters seek therapy. It’s not that we were shocked to learn just how deeply dysfunctional Dennis, Dee, Mac, Charlie, and Frank are, but witnessing each of them bare their souls (and I mean every last bit of it) in front of the unfortunate therapist offers us a deeper understanding of these absolutely absurd individuals than ever before.

“The Gang Dines Out” (Season 8, Episode 9)

Despite the ongoing harshness they exhibit towards each other, it’s the moments when this motley crew genuinely seems to appreciate one another that stand out most. Among these, “The Gang Dines Out” is particularly noteworthy. In this episode, Mac and Dennis, Charlie and Frank, and a solo-dining Dee all end up at Guigino’s, where they engage in escalating competition, only to eventually unite against an unsuspecting third party. As Larry Fitzmaurice put it when he ranked this episode as one of the best in the series, “this group of five dysfunctional, depraved, and interdependent misfits aren’t just suited for each other – they’re destined to be, whether it’s sharing a table or laughing at the same hurtful joke. It’s the most heartwarming episode in a show that has spent 12 seasons resisting the idea of ‘heartwarming.’

“The Gang Misses the Boat” (Season 10, Episode 6)

As a film enthusiast, I find that episodes where the whole crew embarks on a joint mission are equally thrilling as those where each member pursues their unique paths. In this captivating half-hour, for instance, Mac gets himself into romantic misadventures, Frank switches allegiance to another group, Dennis confronts his anger management challenges, while Charlie and Dee engage in exploring the world of “def poetry” and (perhaps, likely, certainly?) share a night together. The title “The Gang Misses the Boat” underscores that the show’s main characters are just as entertaining when they’re apart as they are when they’re together.

“Mac & Dennis Move to the Suburbs” (Season 11, Episode 5)

In some instances, Sunny’s most intelligent storylines push the group far beyond their accustomed environments, and undeniably, Mac and Dennis attempting to thrive in suburbia is a perfect example of this. The hilarious chemistry between McElhenney and Howerton as their characters increasingly frustrate each other is delightful to observe, but it’s the minor details – like the persistent beeping smoke detector, the Applebee’s photos, and the numerous trash bags accumulating throughout the house because perhaps neither man grasps how garbage collection works – that make this episode truly standout.

“Time’s Up for the Gang” (Season 13, Episode 4)

In my opinion, Sunny’s approach to contemporary social issues sometimes falls short, but I found the 2018 portrayal of the #MeToo movement particularly effective. When our local pub, Paddy’s, made a list of bars with poor treatment towards women, we decided to attend an anti-sexual harassment seminar. Frankly, it didn’t go smoothly, but each one of us had a revelation about our own less-than-perfect actions. It might not have led to significant change, but hey, every step forward counts as progress.

“Mac Finds His Pride” (Season 13, Episode 10)

https://youtube.com/watch?v=watch?v=3J6urFp8YZ0

Throughout the series “Sunny,” Mac’s continued concealment of his apparent sexual orientation is a recurring joke. However, in the season-13 finale, the tone shifts dramatically as he reveals his true identity to his father through an intricate and emotionally charged dance routine. This scene is powerful and impactful, standing out among other episodes, and it represents one of “Sunny”‘s most significant accomplishments to date, despite the sudden change in the episode’s overall mood.

“2020: A Year in Review” (Season 15, Episode 1)

During the pandemic, “Sunny” took a two-year break, leaving viewers mostly confined at home. However, the group surprisingly found themselves quite busy during this time. They were implicated in various mischievous activities such as delaying vote counts during the 2020 elections, coloring Rudy Giuliani’s hair, selling raccoon-fur costumes to QAnon followers, and being present at the January 6th Capitol riot. This amusing (even comical) episode is a must-watch, as it showcases the intricate ways in which this band of misfits found themselves entangled in significant political events during their break.

“The Gang Carries a Corpse Up a Mountain” (Season 15, Episode 8)

During their stay in Ireland, many events unfold within the group. Dee gets hit by a car, Mac temporarily becomes a priest, Frank discloses his friendship with Jeffrey Epstein – and that’s merely the beginning. However, the most poignant moment occurs when Charlie, having just met his father for the first time, carries his corpse and angrily reproaches him for not being there for him during his childhood. This emotional outburst from Charlie is quite unexpected – but typical of Sunny, he then (with the help of the gang) carelessly discards the body off a mountain into the rocks instead of the sea as originally intended, nonchalantly dismissing the incident before returning to America.

“Frank vs. Russia” (Season 16, Episode 4)

Among the outstanding episodes of the latest season of “Sunny,” titled “Frank vs. Russia,” stands out with its clever blend of nostalgia and novelty. It references beloved characters from the past (like Uncle Jack!), yet maintains a contemporary feel through a captivating chess-and-beads storyline inspired by recent events. However, it truly shines when it skillfully merges old and new elements, such as when Dennis modifies his notorious D.E.N.N.I.S. system to supposedly aid Mac, who is now dating men. Despite the change in target audience, the emotional manipulation remains a signature trait of “Sunny.

2025-07-09 19:55