Diane Keaton, Oscar-Winning Comedy Star, Dies at 79

One of the film world’s signature stars of the last 50 years has died.

Diane Keaton died on Saturday, October 11th, in California, according to a report in *People Magazine*. Her family has requested privacy, and no further details about her death have been released. She was 79 years old.

Diane Keaton, born Diane Hall on January 5, 1946, was raised in Los Angeles. She adopted the stage name Keaton because another actress was already using her birth name with the actors’ union; Keaton was her mother’s family name. After studying acting in New York and performing on Broadway, she starred alongside Woody Allen in his 1969 play, *Play It Again, Sam*. The play was later adapted into a film directed by Herbert Ross, with Keaton repeating her stage role. Her performance earned her a Tony Award nomination for Best Supporting Actress.

Diane Keaton really started to gain recognition when she landed the role of Kay Adams in Francis Ford Coppola’s *The Godfather*. It was a fantastic performance, and she brought a real vulnerability to the character. What’s even more impressive is she wasn’t just a one-off; she came back for both *The Godfather Part II* and *The Godfather Part III*, really cementing her place in that iconic film saga.

Following her role in *The Godfather*, Diane Keaton became Woody Allen’s most frequent and recognizable co-star throughout the 1970s. She appeared in many of his most successful films from that era, including *Sleeper*, *Love and Death*, *Manhattan*, and his critically acclaimed romantic comedy, *Annie Hall*. Released in 1977, *Annie Hall* was a major award winner, taking home four Oscars: Best Picture (beating out the original *Star Wars*), Best Director, Best Original Screenplay, and Best Actress for Keaton’s performance as Annie Hall.

While Diane Keaton is best known for her iconic roles in *The Godfather* and *Annie Hall*, she consistently starred in films throughout her career, right up until last year. She appeared in a long list of beloved and critically successful movies, including *Looking for Mr. Goodbar*, *Interiors*, *Reds*, *The First Wives Club*, *Father of the Bride* and its sequel, *Marvin’s Room*, *Something’s Gotta Give*, *The Family Stone*, *Book Club* and its sequel, *Book Club: The Next Chapter*. She even received Best Actress nominations for her performances in *Reds*, *Marvin’s Room*, and *Something’s Gotta Give*.

Diane Keaton wasn’t just an actress; she also directed four movies, beginning with *Heaven* in 1987. Her last time in the director’s chair was with the 2000 film *Hanging Up*. As an actress, her final role was in the 2024 movie *Summer Camp*, where she starred alongside Kathy Bates and Alfre Woodard.

Diane Keaton was a remarkably versatile and beloved actress, captivating audiences across different generations. Her passing is a significant loss for film fans, and it’s difficult to picture the movies of the 1970s – or the years that followed – without her presence.

The 40 Best Movies of the Last 40 Years (1985-2024)

40. The Fugitive (1993)

When compiling lists of great films, it’s easy to overlook purely enjoyable movies that you can watch repeatedly just for fun, especially if they don’t deal with deep or complex ideas. However, *The Fugitive* makes seemingly simple action-thrillers look effortless. It’s actually remarkably challenging to create a film with such a gripping mystery, clear action, and strong performances – particularly from Tommy Lee Jones as the relentless U.S. Marshal Sam Gerard. This movie remains endlessly rewatchable because it’s crafted with a level of skill and attention to detail that was uncommon in 1993, and is even rarer today.

39. Holy Motors (2012)

Leos Carax’s *Holy Motors* feels like the most incredible dream you’ll ever experience while awake. It’s a wildly imaginative and moving tribute to film, acting, and life itself—suggesting they’re all interconnected. Denis Lavant delivers eleven fantastic performances as Oscar, a man driving around Paris in a limousine, constantly transforming into different characters, from a motion-capture performer to a gangster and a beggar. While the exact nature of Oscar’s work remains a mystery, the film powerfully demonstrates the enduring magic and unrealized possibilities of cinema, especially at a time when traditional moviegoing and distribution methods are changing.

38. Hard Boiled (1992)

John Woo’s *Hard Boiled* begins with a simple scene: a drink being made. Tequila and soda are poured into a glass, then the glass is slammed onto the bar, mixing the contents. This opening isn’t just about drinks; it hints at the film’s core idea. The movie explores what happens when two very different people are thrown together. Both Chow Yun-Fat and Tony Leung are great actors on their own, but when they work together, the result is explosive and unforgettable – pure movie magic.

37. Matinee (1993)

Joe Dante’s *Matinee* isn’t just a fun trip down memory lane; it cleverly examines the difference between genuine fear and the manufactured thrills offered by cheesy horror films – and by the film’s producer, Lawrence Woolsey (John Goodman). It’s surprising how insightful a movie about a low-budget filmmaker can be.

The film’s warm look back at 1960s B-movies is balanced by the understanding that the real world, both then and now, can be a difficult place. The story centers on Gene (Simon Fenton), a teenager living with his mother and brother on a military base while his father is away at sea during the Cuban Missile Crisis. Gene often takes care of his younger brother Dennis (Jesse Lee) as his mother (Lucinda Jenney) struggles to cope. Constant moves due to his father’s job leave the brothers feeling like outsiders at school. For them, the local movie theater offers a much-needed escape and a sense of happiness.

36. Back to the Future (1985)

At its heart, *Back to the Future* explores a question many teenagers have: What were my parents like when they were young? The film brilliantly builds a story around this idea. Marty McFly, played by Michael J. Fox, is a carefree teen who travels back to 1955 in a time-traveling DeLorean created by his eccentric scientist friend. Once there, he accidentally interferes with his parents’ first meeting, threatening his own existence and forcing him to fix the timeline. With its humor, unique style, beautiful visuals, and fast-paced editing, *Back to the Future* is a nearly flawless example of 1980s Hollywood entertainment.

35. Jackie Brown (1997)

What I really appreciate about *Jackie Brown* is how realistically flawed the characters are. Max Cherry isn’t a cool, intimidating gangster; he’s just a regular guy, a bit down on his luck. And Jackie Brown isn’t a criminal mastermind—she even practices her gun-drawing skills! Even Louis Gara has a relatable moment, forgetting where he parked during a robbery. They feel like real people, and I think some of Tarantino’s later films could benefit from that same level of humanity. When *Jackie Brown* first came out, some viewers were disappointed it wasn’t as flashy or intricate as *Pulp Fiction*, but Tarantino’s more subtle choices are exactly what make it work. The opening credits, reminiscent of *The Graduate*, immediately establish Jackie’s character, and scenes like the one with Ordell and Beaumont are phenomenal. Plus, the film concludes with a truly memorable kiss—not because it’s overtly sensual, but because it feels genuine and imperfect.

34. The Fabelmans (2022)

What strikes you most about *The Fabelmans* is how utterly, beautifully in love with movies Steven Spielberg still is. Seeing this film, you realize that little Sammy Fabelman, the boy captivated by *The Greatest Show on Earth*, never really left him. Spielberg’s clearly become a master filmmaker since then, learning how to wield visuals and sound to evoke every emotion imaginable. But he hasn’t lost sight of *why* he makes movies in the first place.

And *The Fabelmans* is, at its heart, his origin story – a look at the bright and shadowed sides of both filmmaking and life itself. For young Sammy, movies weren’t just entertainment; they were a way to deal with his anxieties and loneliness, though sometimes they also deepened his isolation. Directing became a way to connect with his incredibly artistic mother, brilliantly portrayed by Michelle Williams, but it also risked revealing a painful family secret. Now, decades later, Spielberg has crafted this incredible, deeply personal story, brimming with life, love, joy, and, yes, sadness – everything the best movies always are.

33. Barb and Star Go to Vista Del Mar (2021)

Kristen Wiig and Annie Mumolo, the creators of *Bridesmaids*, reunited for another hilarious comedy, *Barb and Star Go to Vista Del Mar*. They play two best friends who lose their jobs at a furniture store in Nebraska and decide to spend their severance packages on a Florida vacation. While there, they both fall for a handsome stranger (Jamie Dornan, playfully poking fun at his heartthrob image) who is secretly part of a ridiculous plot to unleash genetically engineered killer mosquitoes on the town. Wiig and Mumolo are fantastic, with witty dialogue covering everything from Tommy Bahama shirts to the power of the name Trish – their script is sure to become instantly quotable. In difficult times, *Barb and Star* arrived as a bright and joyful escape, offering a much-needed dose of fun and optimism.

32. Inside Out (2015)

Pete Docter was known as Pixar’s creative force even before becoming its chief creative officer. He contributed as a writer to beloved films like *Toy Story*, *Toy Story 2*, and *WALL-E*, and directed some of Pixar’s most acclaimed movies, including *Monsters, Inc.*, *Up*, and *Inside Out*. *Inside Out* is a remarkably imaginative story about the emotions inside the mind of an 11-year-old girl named Riley. When Riley moves from Minnesota to San Francisco, her life is disrupted, leading to a conflict between her personified emotions within her brain. The film’s depiction of Riley’s inner world is visually stunning and consistently engaging. Beyond its creativity, *Inside Out* is a profoundly insightful film about the vital role sadness and grief play in our lives.

31. The King of Kong: A Fistful of Quarters (2007)

The game *Donkey Kong* is a surprisingly accurate reflection of life. It’s incredibly challenging, often unfair, and success often feels like a matter of luck. You might triumph sometimes, but you’re just as likely to be crushed by unexpected obstacles – like a gorilla stealing your partner. Even achieving great things doesn’t offer lasting victory; ultimately, failure is inevitable. And sometimes, you even have to contend with strange, unpredictable people.

That’s why *The King of Kong* isn’t just a documentary about competitive *Donkey Kong*; it’s a film about the human experience.

30. Memento (2000)

Don’t dismiss *Memento* as just a clever trick. While it’s true the film has a very complex structure – arguably one of the most complicated ever created – the way the timelines jump around isn’t just for show. It deliberately disorients the viewer, putting them inside the mind of Leonard Shelby (Guy Pearce), the film’s protagonist, who suffers from a rare form of amnesia that prevents him from forming new memories.

Leonard is on a quest to find his wife’s killer, and the film begins by seemingly showing his success, then rewinds to reveal the truth. *Memento* quickly established Christopher Nolan as a promising director, but the film itself isn’t about coolness; it’s a tragic story about a man desperately trying to find meaning in his life. Though Nolan continued to experiment with filmmaking techniques and explore similar themes in his later work, he largely left behind the dark humor present in *Memento* – from the confusing chase scene where it’s unclear who’s chasing whom, to the ironic name of Leonard’s hotel, the “Discount Inn” (a nod to how Leonard constantly dismisses the story of another man with memory problems).

29. L.A. Confidential (1997)

Just how many layers of nostalgic reference are at play with *L.A. Confidential*? The film is set in the 1950s, clearly inspired by the 1970s classic *Chinatown*, and was made in the late 1990s – a time when large-scale, expensive crime dramas with mostly unknown actors were still feasible (with Kevin Spacey and Kim Basinger being the only established stars). Like the James Ellroy novel it’s based on, *L.A. Confidential* dismantles the idea that the 1950s were a simpler, more idyllic era in Los Angeles. As one character points out, that’s a manufactured image, and the real story was largely hidden until Ellroy and director Curtis Hanson brought it to light.

28. The Prestige (2006)

Christopher Nolan’s *The Prestige* perfectly blends his signature style—complex timelines, unexpected twists—with his recurring interests, like flawed heroes and the impact of loss, to create a truly powerful film. Set in Victorian London, the movie follows two competing magicians, played by Christian Bale and Hugh Jackman, whose rivalry escalates to dangerous levels, pushing them to both innovate and commit terrible acts. *The Prestige* is a story within a story, exploring the sacrifices artists make for their craft and the inherent duality of human nature. It remains incredibly rewarding to watch, even knowing the shocking twists, as each viewing reveals new details and the brilliance of Nolan’s carefully crafted foreshadowing—if you pay close attention.

27. The Social Network (2010)

Whether David Fincher’s and Aaron Sorkin’s depiction of Facebook’s beginnings is entirely accurate is open to discussion. However, they undeniably captured a specific personality type with Mark Zuckerberg, as played by Jesse Eisenberg: a brilliant, frustrated, privileged individual craving connection and validation. Many questioned Fincher’s choice to make a film about Facebook in 2010, but it’s now apparent it was a spiritual follow-up to *Fight Club*, another story of a resentful, isolated man whose outburst of anger has unforeseen results. A crucial element of the film is Justin Timberlake’s casting as Napster founder Sean Parker – essentially Zuckerberg’s rebellious alter ego. Timberlake and Eisenberg share a striking resemblance – they could be brothers if fortune had favored one over the other. Mark clearly admires Timberlake’s character and feels he’s almost within reach of that same success and power.

26. Nickel Boys (2024)

It’s rare to see a truly original film, one that feels genuinely new and pushes the boundaries of cinema. But sometimes, a movie like *Nickel Boys* comes along. This film is bold, unique, and offers a distinctive perspective – actually, two. Director and co-screenwriter RaMell Ross made a striking choice: to film almost the entire adaptation of Colson Whitehead’s Pulitzer Prize-winning novel from the viewpoints of the two main characters. The incredible camerawork by Ross and cinematographer Jomo Fray immerses you in the experiences of these young men as they struggle to survive at a Florida reform school in the 1960s. It’s baffling that Fray wasn’t nominated for an Oscar. This technique could easily feel gimmicky, but in Ross’s hands, it creates a genuinely fresh way of seeing the world – and perhaps a glimpse into the future of filmmaking.

25. Past Lives (2023)

This moving and poignant film explores the unseen connections that shape our lives – whether you call it fate or destiny. It focuses on Nora and Hae Sung, two people who feel deeply connected but struggle to stay together. They cross paths at different points in their lives – as children, in college, and as adults – and each time, life has changed, but their bond remains. However, by their final meeting, Nora is married to Arthur. The film delicately portrays this love triangle, leading to a heartbreaking conclusion that will leave you thinking about the defining moments and choices in your own life, and how their significance may only become clear with time.

24. Boyhood (2014)

For twelve years, director Richard Linklater secretly filmed scenes with the same actors – a boy (Ellar Coltrane), his mother (Patricia Arquette), and his sister (Lorelei Linklater) – a few days each year. While some might see this as a self-indulgent project, the result is a fascinating look at American life in the early 2000s, and a deeply moving portrayal of one family’s love, struggles, and sacrifices. Unlike most films, *Boyhood* has a truly special connection to time. Seeing the actors actually age on screen adds an extra layer of emotion to many scenes, making joyful moments sweeter and sad ones even more poignant. When Patricia Arquette reflects on her life at the film’s end, it’s informed by a full twelve years of genuine experiences. As the late film critic Roger Ebert once said, “Movies are windows into our world.” And *Boyhood* feels like a film that throws those windows wide open.

23. Catch Me If You Can (2002)

Despite being a fun and lighthearted film, *Catch Me If You Can* is also a surprisingly thoughtful look at loneliness and the importance of family. It features a fantastic cast, including Leonardo DiCaprio as the clever con artist Frank Abagnale Jr., Christopher Walken as his frustrated father, Jennifer Garner and Amy Adams as his romantic interests, and Tom Hanks as the determined, serious FBI agent Carl Hanratty.

22. Mad Max: Fury Road (2015)

Many consider *Mad Max: Fury Road* the best car chase movie made this century, and it’s easy to see why. Beyond the thrilling action, the film is surprisingly spiritual, echoing the Biblical story of Exodus. It’s like a journey away from a ruined world, seeking a new paradise, with Charlize Theron’s Furiosa leading a group of strong women. Tom Hardy’s Max acts as their guide, a flawed hero who helps them find safety but can’t share in their ultimate destination. George Miller’s film proves that action movies can be both incredibly exciting and intellectually engaging. Anyone who says otherwise is just trying to start an argument.

21. Killers of the Flower Moon (2023)

At over 80 years young, Martin Scorsese hasn’t lost a step. He’s still challenging himself – and us, the audience – and continues to get phenomenal performances from his actors. He keeps circling back to the ideas that define his best work: how wealth can both attract and destroy, and the grim underbelly of American history. This time, he tackles the horrific “Reign of Terror” inflicted on the Osage Nation in the 1920s, after oil was discovered on their Oklahoma land, making them targets for greedy neighbors. We see this play out through the story of Ernest Burkhart (Leonardo DiCaprio), who marries into an Osage family, specifically Mollie (Lily Gladstone), an oil millionaire. Honestly, I find myself saying this with each new Scorsese film, but it feels especially true with *Killers of the Flower Moon*: if this *is* his last movie, it’s a stunning and fitting end to an extraordinary career.

20. Chungking Express (1994)

Beyond its memorable soundtrack, striking visuals, and captivating love stories, *Chungking Express* brilliantly portrays the feeling of city life. It captures the loneliness you can experience even in a crowded place, the longing for open space, the fleeting nature of connections, the simple pleasure of a good song in a bar, and the curious nature of people you encounter late at night.

19. Boogie Nights (1997)

Paul Thomas Anderson’s film is a funny, sad, and nostalgic look at the California porn industry’s heyday. It moves quickly through the era, introducing a memorable cast of characters, including a filmmaker reminiscent of Burt Reynolds and a troubled mother figure played by Julianne Moore. The film isn’t just about these individuals, though; it’s a broader exploration of America in the late 1970s – its dreams, its flaws, and its hidden desires.

18. Ran (1985)

Akira Kurosawa’s *Ran* is my favorite film of his. It’s unique because it was made later in his career and, unlike most of his films, is in color. I especially love it because of how he uses color – particularly in the vibrant costumes – to powerfully emphasize key moments, like a dramatic finishing touch to each scene.

17. The Matrix (1999)

One of the few real perks of getting older is revisiting movies and seeing how well they stand the test of time. I remember seeing *The Matrix* when it first came out, and it was such a thrilling experience that I can still picture the exact theater, auditorium, and even my seat! The trailers were promising, but the movie itself was truly captivating.

More than 20 years later, it still is. My only complaint about *The Matrix*? Don’t try to watch it while you’re working – you’ll end up re-watching it for the 65th time and never get anything done.

16. The Diving Bell and the Butterfly (2007)

2007 was a fantastic year for movies, but the one that really stayed with me was *The Diving Bell & The Butterfly*. It’s Julian Schnabel’s beautiful adaptation of Jean-Dominique Bauby’s memoir about living with locked-in syndrome. Bauby’s story, and the way the film captures his message of embracing life, had a profound impact on me. I left the theater that day and knew I wanted to propose to my girlfriend – and 15 years and two kids later, I’m so glad I did! Revisiting the film recently, I was reminded of just how powerful it still is.

15. Die Hard (1988)

Does anyone really need convincing that *Die Hard* is one of the greatest movies ever made? It’s pretty obvious! Think about Bruce Willis’ amazing performance as John McClane, the New York cop just trying to enjoy a vacation, or the fantastic action direction by John McTiernan. Plus, it’s the perfect Christmas movie… with a lot of gunfire.

14. Close-Up (1990)

Considered a landmark film in Iranian cinema, *Close-Up* tells the true story of a man who pretended to be a famous filmmaker and conned a family in Tehran. Director Abbas Kiarostami uniquely cast the real people involved to play themselves, filming both parts of the legal proceedings and reenactments of events leading up to his involvement. The film’s innovative mix of documentary and fictional storytelling, and its exploration of themes like celebrity and social class, continues to be highly influential and original.

13. The Truman Show (1998)

It’s easy to wonder if we’re living in a simulation, especially when you consider how accurately the movie *The Truman Show* predicted our current world. It feels impossible that a film could have foreseen our loss of privacy, the constant advertising, and the general anxieties of modern life. But beyond the idea of a reality TV show, the first half of the movie is a surprisingly relatable story about having a mid-life crisis and questioning everything at around age 40 – that feeling of suddenly realizing, “Is this really my life?”

12. Zodiac (2007)

David Fincher is known for directing thrillers about serial killers, but *Zodiac* is more than just a crime story. It’s a look at San Francisco over several decades, seen through the perspectives of three men obsessed with solving the Zodiac Killer case. We follow a police inspector (Mark Ruffalo), rumored to have inspired the film *Bullitt*, a newspaper reporter (Robert Downey Jr.) who became a target of the Zodiac, and an amateur detective (Jake Gyllenhaal) unable to let the mystery go, even after the killings stop. What makes *Zodiac* stand out is its portrayal of how all-consuming an obsession can be. Fincher expertly pulls viewers into the complex investigation with dynamic camera work and editing. By the film’s ending—which cleverly circles back to the beginning after a tense two and a half hours—you’ll fully understand Robert Graysmith’s relentless drive.

11. Inside Llewyn Davis (2013)

The films of Joel and Ethan Coen often feel like collaborations between two voices, and *Inside Llewyn Davis* is particularly focused on this idea. The movie portrays the New York folk music scene of the early 1960s, but it’s also a story about the small misfortunes that happen to a talented musician (Oscar Isaac, in a career-defining role) after losing his musical partner. It’s fitting that the most beautiful song Llewyn plays, “Fare Thee Well,” sounds incomplete when performed solo – it truly needs another voice.

10.Lady Bird (2017)

Greta Gerwig’s *Lady Bird* really struck me with its focus on duality. Everything seems to come in pairs: our main character has two first names, navigates two romances, and even has two best friends. The film beautifully charts a school year filled with two semesters, two school plays, dances, and parties. But it’s more than just repetition; it’s a clever way to explore the weight of choice. As a teenager, every decision – which college to apply to, even which church to attend – feels monumental, and Gerwig really captures that feeling. It made me realize, in a lot of ways, those decisions *are* incredibly important.

9. Eternal Sunshine of the Spotless Mind (2004)

I can’t recall exactly when or where I first watched *Eternal Sunshine*, but it was around 20 years ago while I was living in New York City. The details of that initial viewing have faded with time, like so many memories do. Ironically, that makes me appreciate the film even more now than I did when it came out in 2004. What’s so brilliant about *Eternal Sunshine of the Spotless Mind* is that it uses a science fiction idea – a couple erasing each other from their memories – to explore how we naturally forget things. Jim Carrey and Kate Winslet create one of cinema’s most memorable couples, largely because their relationship is destined to fail. Ultimately, all relationships end somehow, like a beach house slowly being swallowed by the ocean.

8. Pulp Fiction (1994)

While *Pulp Fiction* might not be the most copied film of the ’90s today, it was hugely influential for a time. The poor quality of many attempts to copy it actually highlights just how talented Quentin Tarantino is, both then and now.

*Pulp Fiction* is a strange mix of things that somehow all fit together. It’s a grand story about crime in Los Angeles, but also a deep look at the people involved. It jumps between wildly fantastical elements – like mysterious briefcases and secret clubs – and incredibly ordinary moments, such as conversations about foot rubs and international fast food. It’s epic and intimate, funny and sad, violent and silly. It’s simply *Pulp Fiction*.

7. Do the Right Thing (1989)

Spike Lee’s film, set during a scorching summer day in Brooklyn, powerfully explores racial tensions – and sadly, its themes still resonate today. The story centers on a neighborhood where life revolves around an Italian-owned pizzeria, which becomes the focal point of a riot after a Black man is fatally shot by police. The film leaves viewers pondering whether Mookie, a key character, made the right decision by throwing a trash can through the pizzeria window, and perhaps the very act of questioning that decision is more important than finding a definitive answer.

6. American Movie (1999)

This charming and often humorous documentary follows Mark Borchardt, an aspiring filmmaker, as he tries to finish a film he’s been working on for years. It’s a surprisingly poignant look at chasing dreams and the frustration of not always reaching your goals. Mark is passionate about making movies, but constantly faces obstacles. The film is also a heartwarming story about the friendship between Mark and his friend Mike, who helps him with his low-budget projects. It’s an enjoyable film for younger viewers, but gains a deeper, more emotional resonance as you get older. Many consider it to be one of the best American films ever made.

5. Take Shelter (2011)

Having experienced panic attacks myself, I can confidently say that *Take Shelter* is a masterpiece in portraying the experience of anxiety. The film centers on Curtis LaForche (Michael Shannon), a family man plagued by terrifying nightmares of catastrophic storms and a growing sense of dread. Driven by a phenomenal performance from Shannon, and equally strong work from Jessica Chastain as his wife, the movie perfectly captures the vicious cycle of fear – Curtis worries he’s losing his mind, a fear worsened by his family history of mental illness, creating even more anxiety. While many find the ending open to interpretation, I see it as the only logical conclusion. The film demonstrates that this kind of anxiety can’t be overcome or blocked out, even when trying to protect those you love. It can only be managed with understanding and the help of supportive relationships.

4. Once Upon a Time in Hollywood (2019)

Actor Rick Dalton and his stuntman, Cliff Booth, have lunch with producer Marvin Schwarz at the Musso & Frank Grill. Marvin suggests Rick star in Italian Westerns, but Rick is unimpressed and feels deeply discouraged, believing his career is over. He breaks down crying as soon as he leaves the restaurant. The camera focuses on the Musso & Frank Grill sign, emphasizing its history as “Oldest in Hollywood.”

While Rick isn’t actually old news, he feels that way in this moment, realizing his time as a leading man is running short. *Once Upon a Time in Hollywood* is a brilliantly crafted film, full of subtle details like this one. It’s both a look back at a changing time in American history and a loving tribute to the golden age of filmmaking, which itself was facing an uncertain future.

3. Groundhog Day (1993)

Few comedies are as insightful as *Groundhog Day*. Bill Murray delivers a standout performance as Phil Connors, a self-centered TV weatherman who, while covering the Groundhog Day celebrations in a small Pennsylvania town, finds himself reliving the same day over and over. Essentially, the movie follows a man who initially believes he’s all-powerful, gradually transforms into someone truly good, and ultimately discovers what it means to be human.

2. Goodfellas (1990)

Even thirty years after its release, Martin Scorsese’s *Goodfellas* is widely considered one of the best and most influential films of the 1990s. It’s a fantastic pairing with his later film, *The Irishman*, if you’re up for a long movie marathon. The film chronicles the life of a young man, played by the late Ray Liotta, as he climbs the ranks of the mafia, experiencing both lavish feasts and simple, meager meals along the way. Everything about the movie – the acting, script, editing, cinematography, and music – is flawless. It’s still hard to believe that *Dances With Wolves* won the Best Picture Oscar instead of *Goodfellas*.

1. Hoop Dreams (1994)

The documentary *Hoop Dreams* is about far more than just basketball. It follows the boys not through their basketball careers, but to their high school graduations. As Spike Lee points out when visiting a college recruiting camp, the world of competitive sports is heavily influenced by money. The film leaves you feeling like there are actually two games happening: the one played on the court, and a separate, unfair game played by the adults involved. It makes you wonder what options William and Arthur had, and what else they could realistically dream of achieving.

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