It’s been a while since HBO Max became just Max, and it still doesn’t make any sense, and we’re still not used to it. It only makes sense because OF COURSE the same geniuses who innovated the practice of removing exclusive content from streamers would also want to distance that streamer from the most prestigious name in TV. We wouldn’t want anybody thinking Max was classy, would we? So dump the HBO from the name, focus more of the promotion on the bottom-feeding “reality” shows Discovery is known for, and, yes, try to charge even more for it after all of that. Let’s see how that goes. But hey: at least it still has a lot of great comedies to stream. And yes, that’s what this entire post is about: the best comedies on Max.
Despite all the turmoil and nonsensical corporate decisions, Max still has the best, deepest, and most varied selection of comedies of any streamer at the moment. Good luck finding this many classics or pre-’90s comedies on the other services. Max today feels like Netflix did a decade ago, before the streaming world splintered into a dozen different walled off rivals. That’s a good thing.
Also, my standard disclaimer for these comedy lists: I’m not judging these exclusively on their cinematic qualities. Acting, storytelling, and technique are all apart of the equation, but the most important single facet is how much it makes me laugh.
With that out of the way, let’s get to it. Here are the best comedies on Max today.
1. The Great Dictator
Year: 1940
Director: Charles Chaplin
Stars: Charles Chaplin, Paulette Goddard, Jack Oakie, Reginald Gardiner
Rating: G
Charlie Chaplin’s first “talkie” was a biting satire that he wrote, directed, produced, scored, and starred in-as both of the lead roles, a fascist despot who bears a rather marked resemblance to Adolf Hitler and a persecuted Jewish barber. Good satire can be powerful, and this film was: Released while the United States was still formally at peace with Germany, it stirred greater public attention and condemnation of the Nazis and Mussolini, anti-Semitism and fascism. (That said, Chaplin later recounted that he could never have made the satirical film even a year or two later, as the extent of the horrors in German concentration camps became clearer.) The choice to play both the tyrant and the oppressed man was an inspired one, underscoring the frightening but inescapable truth that we all contain a little bit of both characters. This is a strikingly pertinent film for our particular moment in history, and well worth dusting off and queueing up not only for its incredible craft but for its resonance as a study in projection. —Amy Glynn
2. Singin’ in the Rain
Year: 1952
Directors: Stanley Donen, Gene Kelly
Stars: Gene Kelly, Debbie Reynolds, Donald O’Connor, Jean Hagen, Rita Moreno
Rating: G
The most legendary of Hollywood musicals, Singin’ in the Rain is a warm, beautiful, feather-light look at Hollywood on the cusp of the talkie revolution, with timeless performances from Gene Kelly, Debbie Reynolds and Donald O’Connor. Musicals can be an acquired taste in the year 2020, but this is one of those legit classics that pretty much anybody interested in the movies should see at some point in their life. It’s a charming, romantic trifle that’s made with perfect precision, and one of the best comedies on Max.—Garrett Martin
3. Dr. Strangelove Or: How I Learned to Stop Worrying and Love the Bomb
Year: 1964
Director: Stanley Kubrick
Stars: Peter Sellers, George C. Scott, Sterling Hayden, Slim Pickens
Rating: PG
While attempting to adapt Peter George’s novel Red Alert for the big screen, director Stanley Kubrick found that he kept needing to cut out certain real-life details about the emergency nuclear bomb procedures because they were simply too absurd to work in a serious drama. Deciding to rewrite the project as a dark comedy, he recruited renowned satirist Terry Southern to help pen the script. From there, it’s all history. To this day, Peter Sellers’ three very different (and very funny) performances remain a feat by which few actors have matched. Moreover, the image of Slim Pickens riding the bomb to its destination as well as the final montage of destruction set to the wistful “We’ll Meet Again” are the stuff of movie legend. Worldwide Armageddon has never been so hilarious.—Mark Rozeman
4. A Shot in the DarkYear: 1964
Director: Blake Edwards
Stars: Peter Sellers, Elke Sommer, George Sanders, Herbert Lom
Rating: PG
Amazing to think that when the first film in the Pink Panther series was made, it was intended as a vehicle for its top-billed star David Niven. Wisely, director Blake Edwards realized the true star of the show was the bumbling French policeman Inspector Clouseau, as embodied by the brilliant Peter Sellers. So, they rushed another film into production (it was released in the States a mere three months after The Pink Panther) and comedy greatness was born. Ever the sport, Sellers quite literally threw himself into the part, crashing and stumbling through his investigation of murder and mangling the English language each step of the way. Try as they might to recapture the fire of this first sequel, nothing quite matched the freewheeling spirit of A Shot in the Dark. —Robert Ham
5. The Naked GunYear: 1988
Director: David Zucker
Stars: Leslie Nielsen, Priscilla Presley, Ricardo Montalban, George Kennedy
Rating: PG-13
The final hoorah from the comedy trio David Zucker, Jim Abrahams and Jerry Zucker—ZAZ for short—The Naked Gun is so stupid it’s hilarious. This, of course, was ZAZ’s secret weapon in films like Airplane!, and in Leslie Nielsen’s stone-faced imbecility they found their muse. A former dramatic actor, Nielsen rejuvenated his career by playing Frank Drebin, a hapless L.A. police detective trying to prevent the assassination of Queen Elizabeth. (And in his courting of possible femme fatale Priscilla Presley, he taught us the importance of wearing full-body condoms.) A wonder of slapstick and deadpan silliness, The Naked Gun makes jokes about terrorists, gay panic, boobs, even “The Star-Spangled Banner.” There’s a character named Pahpshmir. Good lord, it’s all so gloriously idiotic. —Tim Grierson
6. Modern Times
Year: 1936
Director: Charles Chaplin
Stars: Charles Chaplin, Paulette Goddard, Henry Bergman
Rating: G
If time is a flat circle, then Modern Times is like a flat sprocket—the travails of the Little Tramp navigating a mechanical world being so incessant and repetitive that elements like luck and hope only serve to spur along Chaplin’s farce even though they hold little grip on his characters’ futures. Not much changes for the Little Tramp throughout: He tries to survive, and yet the institutional system craps him back out to where he started, desperately hungry and penniless, left with nothing to do but try again. This was also Chaplin’s last go as the Tramp, and it’s easy to imagine that, throughout the film’s many misadventures—joined by equally good-natured partner in crime, the gamin (Paulette Goddard)—as he gets sucked up and sublimated into the modern industrial machine, this “disappearance” was kind of by design. It’s a weird way for Chaplin’s beloved character to go out, but so are the many ways in which Chaplin shows how the modern industrial machine becomes part of the Tramp, too. He may get squeezed through a giant, sprocket-speckled apparatus, becoming one with its schematics, but so too does the assembly line—with all that twisting, wrenching, and spinning—impress itself onto the Tramp, leaving him unable after a long shift to do anything but waggle his arms about as if he’s still on the assembly line. It’s no wonder, then, that the President of Modern Times’ factory setting bears a striking resemblance to Henry Ford: Chaplin, who toured the world following the success of City Lights, witnessed the conditions of automobile lines in Detroit, how the drudgery of our modern times weighed on young workers. The Great Depression, Chaplin seems to be saying, was the first sign of just how thoroughly technology can kill our spirits, not so much discarding us as absorbing our individuality. Modern Times, then, is a film with a conscious far beyond its time, a kind of seamless blending of special effects, sanguine silent film methods and radical fury.—Dom Sinacola
7. Safety Last!
Year: 1923
Directors: Fred C. Newmeyer, Sam Taylor
Stars: Harold Lloyd, Mildred Davis, Bill Strother
Rating: NR
“I shouldn’t have bothered scoring the last 15 minutes,” Rodney Sauer of the Mont Alto Motion Picture Orchestra told me after accompanying Safety Last! at the San Francisco Silent Film Festival. He said he and his ensemble couldn’t even hear themselves over the uproarious laughter in the Castro Theatre during Harold Lloyd’s famous building-scaling sequence. The scene, with its iconic clock-hanging finale—is such a perfect mix of suspense and comedy that it doesn’t much matter that the rest of the film seems to exist merely as a lead-up. Ultimately it’s one of the best comedies on Max. —Jeremy Mathews
8. A Serious ManYear: 2009
Directors: Joel and Ethan Coen
Stars: Michael Stuhlbarg, Richard Kind, Fred Melamed, Amy Landecker, Adam Arkin
Rating: R
Working with few recognizable stars, the Coens have made a funny but odd and inquisitive film about guilt. It’s also their most Jewish film to date, a film about physics professor Larry Gopnik and the Jewish subculture of a medium-sized late-’60s American town. Larry’s life begins to fall apart when his wife says she wants a divorce, and in the great unraveling that follows, the Coens have made Kafka’s implications explicit. The K word is often slapped onto any old symbolic nightmare, but Kafka’s own work was actually very funny, even though he could slip into gray areas without much warning. The Coens can, too. A Serious Man is one of the most fascinating, maybe even heartfelt, renderings of a Kafkaesque sensibility that I’ve seen. —Robert Davis
9. Office Space
Year: 1999
Directors: Mike Judge
Stars: Peter Gallagher, Jennifer Aniston, Gary Cole, David Herman, Ajay Naidu, Diedrich Bader, Stephen Root, Richard Riehle, John C. McGinley, Paul Willson
Rating: R
Great comedy almost always has a dark heart. (The flipside is also true of great horror: It almost always teeters on the edge of farce). But this makes sense: Laughter is our response to absurd and unexpected contradictions; comedy needs its darkness to fully flourish. Mike Judge, the writer/director of Office Space, knows this well. His humor concerns the lowest, saddest schmucks on the corporate ladder (thus 99% of us can relate) who mostly feel dead inside, turning to Kung Fu films and cheap beer to escape. It’s a subject as old as capitalism itself: Most of us are unhappy, not doing what we want, feeling our dreams escaping us more and more with each passing day. For protagonist Peter Gibbons (Ron Livingston), his goal is a subversive joy: Independently, from no wellspring of societal angst (unlike, say, The Graduate’s Benjamin Braddock), he wants to do nothing. And besides being a hilarious antidote to scores of predictable, cookie-cutter hyperactive hero-protagonists, his needs feel absolutely real, and is what the corporate rat race deserves in an anti-hero. The do-gooder replaced by the do-nothing. It also helps that Judge has a cast perfectly on board with his tone. Together, they turn caricature into depth, a cartoon into vivid life. —Harold Brodie
10. House
Year: 1977
Director: Nobuhiko Obayashi
Stars: Kimiko Ikegami, Miki Jinbo, Kumiko Ohba
Genre: Comedy, Horror
Rating: NR
Movies are rarely, if ever, as whirringly rich and strange as House. The 1977 fairy-tale-as-fever-dream from Japanese director Nobuhiko Obayashi was the debut of a guy who was known mostly for his TV commercials. Given a shot at making his first feature by a struggling studio that had nothing to lose, Obayashi did what any aspiring auteur would do: He went to his 11-year-old daughter Chigumi for ideas. What they came up with is a tragi-comic festival of the uncanny about a posse of seven Japanese schoolgirls, a maiden aunt with heartbreaking secret, her freaky-ass white cat named Snowflake and the house of the title, an ooky-spooky hallucination out of gothic myth and Japanese folklore, jazzed by an animated, ADD-afflicted spirit like something from the minds of Tex Avery and Busby Berkeley on crack. Though: No summary really does House justice, and every little thing about it demands attention, from the schoolgirls themselves—precocious archetypes who go by the nicknames Gorgeous, Melody, Fantasy, Prof, Sweet, Mac and Kung Fu—to the anything-goes flourishes of gimmick and technique, which evoke everything from silent film to children’s shows, classic surrealist cinema to Italian giallo. Obayashi crams every frame with a surplus of mad ideas, as if his background in 30-second spots demanded he never let the screen remain calm for an instant. House suggests that the nitrous-oxide hyperdrive of Japanese pop culture—as vivid now as ever—is a brilliantly imagined, if not in fact transcendental brand of therapy. —Steve Dollar
11. Eighth Grade
Year: 2018
Director: Bo Burnham
Stars: Elsie Fisher, Daniel Zolghadri, Fred Hechinger, Imani Lewis, Luke Prael, Catherine Oliviere, Josh Hamilton, Emily Robinson, Jake Ryan
Rating: R
In Eighth Grade, the feature debut of comedian-singer-songwriter Bo Burnham, and one of the best comedies on Max, you’re either a Kayla (Elsie Fisher) or you know a Kayla from your days as an over-it-all punk-ass. The distinction is key to your experience. The film stages a too-real reenactment of middle school’s rigors, but it’s the people we endure those rigors with who shape our turbulent pubescence. Sure, sitting through Ms. Hawking’s ornithology lessons was hell, but hell’s preferable to striking up conversation with your classmates. Burnham uses the awkward terrain of juvenile social interaction as Eighth Grade’s focal point, painting the daunting exercise of talking to other kids as a stairway to embarrassment. We meet Kayla pre-humiliation, recording clips for her YouTube channel in her room, dispensing life advice in the coltish manner of a newly minted teen. She’s extraordinarily inarticulate, but in her ramblings we find the profound insight only a 13-year-old can offer. “Aren’t I always being myself?” she says to her camera, the sage instructing the benighted. “Well, yeah, for sure.” She’s a self-help layman, but her sincerity is charming. Don’t change who you are to impress others. Words to live by. Kayla, like anyone else trying to stay afloat in the sometimes cutthroat world of middle school, sells out her ideals almost immediately, a defensive posture to deflect her loneliness. Being a teenage girl isn’t easy. Occasionally, it’s perilous. That Eighth Grade so genuinely conveys those difficulties and dangers is miraculous considering its source. Burnham invites us to recall our own adolescence, and also to consider how adolescence has changed in the time of social media. It’s compassionate, radiating retroactive kindness for the children we all were to soothe the adults we are now. —Andy Crump
12. Election
Year: 1999
Director: Alexander Payne
Stars: Matthew Broderick, Reese Witherspoon, Chris Klein
Rating: R
A high-school election for student body president turns into a darkly comic satire on politics and sexuality in one of Alexander Payne’s uproarious takedowns of Midwestern values. The election turns into a struggle of wills between Matthew Broderick’s wormy high-school teacher and Reese Witherspoon’s overbearing know-it-all Tracy Flick, but resentful mediocrity doesn’t stand a chance against relentless ambition. With a hyper-capable schoolkid surrounded by hilariously flawed characters, Election could be Rushmore’s cynical classmate.—Curt Holman
13. Metropolitan
Year: 1990
Director: Whit Stillman
Stars: Carolyn Farina, Edward Clements, Chris Eigeman, Taylor Nichols, Allison Parisi, Dylan Hundley
Rating: PG-13
There have been nearly as many “next Woody Allens” in film as there have been “next Michael Jordans” in basketball or “next Bob Dylans” in music, but sometimes the moniker fits. In Whit Stillman’s debut, he staked his claim as the Woody of the upper-class WASPy NYC set and won a whole army of loyal followers. For good reason, too—seldom has any director, regardless of experience, so deftly juggled dialogue that could so easily have delved into too-clever-by-half-isms, or trained such a sympathetic eye on a sometimes questionable nostalgia for the end of an age. Most of all, though, seeing Metropolitan just makes you feel smart and witty and somehow elevated. Not bad for the price of a movie ticket.—Michael Dunaway
14. Barbie
Year: 2023
Director: Greta Gerwig
Stars: Margot Robbie, Ryan Gosling, America Ferrera, Issa Rae, Hari Nef, Simu Liu, Will Ferrell
Rating: PG-13
Bursting with big ideas on the complexities surrounding womanhood, patriarchy and the legacy of its eponymous subject, Barbie scores a hat trick for its magnificent balance of comedy, emotional intelligence and cultural relevance. The picture begins with a playful homage to 2001: A Space Odyssey’s Dawn of Man sequence. Except, in Gerwig’s prelude, the apes are young girls and the wondrous discovery they make is not a monolith, but a 100-foot tall bathing-suit-wearing Barbie (Margot Robbie), who is there to put an end to Planet Earth’s sexism with her mere aspirationalism. Life is idyllic until Robbie’s Barbie, who refers to herself as Stereotypical Barbie, begins to experience an unprecedented existential crisis. These uncharacteristic anxieties, coupled with the fact that her once-permanently-tippy-toed feet have fallen flat, lead Barbie on a quest to the Real World in hopes of returning back to her normal, carefree self. When her adoring Ken (Ryan Gosling) joins her in her cross-realm voyage, ideologies are swapped, havoc is wreaked and major changes are brought upon Barbie Land. Gerwig is grappling with these heavy ideas of patriarchy and gender, but Barbie always maintains a delightful sense of play and lightheartedness. This is largely due to the pink, campy, absurd and absolutely bewitching set work created by Barbie’s production designer, Sarah Greenwood, and set decorator, Katie Spencer. The incredible sets that we see in the film are real, tangible places whose presence create a nostalgic desire to feel, grab and touch. The believability of the sets—“this is a real Barbie Dream House and Robbie is a real life Barbie doll,” we think—makes for an interesting meta layer for the film. This sense of self-awareness touches almost every aspect of Barbie, from the set design to the campy performances and even its handling of its source material. Writers Gerwig and Noah Baumbach obviously have a soft spot for Robbie’s character, and the beauty of humans in general, but they don’t allow their work with a large corporation like Mattel to prevent them from exploring Barbie’s complicated legacy throughout the film. Like its protagonist, Barbie is all the things all at once. Funny. Sentimental. Entertaining. Confrontational. Celebratory. Heartfelt. Heartbreaking. Kooky. Emotional. And, maybe most interestingly of all, a damn good time capsule for what was exciting and frightening in mainstream culture at this particular societal moment.—Kathy Michelle Chacón
15/16. Bill and Ted’s Excellent Adventure / Bill and Ted’s Bogus Journey
Year: 1989 / 1991
Director: Stephen Herek / Pete Hewett
Stars: Keanu Reeves, Alex Winter, George Carlin, Bernie Casey, Amy Stock-Poynton; William Sadler, Joss Ackland, Pam Grier
Rating: PG
Rating: PG
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In the end we just can’t pick between these two. Both movies are classics, but for different reasons. Both movies are part celebration and part knowing parody of the California party dude stereotype that was so popular in the ’80s, and although Excellent Adventure might be the more beloved movie today because of its historical set pieces and the simple fact that it came first, Bogus Journey is the stronger, smarter, and, yes, more challenging movie. It’s a surreal trip through the afterlife that at times feels like Tim Burton with more edge, succeeding at both low brow, crowd-pleasing humor and slightly deeper, more philosophical material. (Yeah, today’s pretentious Rick & Morty Redditors probably love this movie.) Both are far better than they need to be, two hilarious bookends that prove that sequels can be great, actually.–Garrett Martin
17. Legally Blonde
Year: 2001
Director: Robert Luketic
Stars: Reese Witherspoon, Luke Wilson, Selma Blair, Jennifer Coolidge, Victor Garber, Matthew Davis, Holland Taylor
Rating: PG-13
If you like the color pink and are currently between the ages of 25 and 45, there’s a good chance you’ve practiced the “Bend-and-Snap” at home at least once in your life. Legally Blonde, starring Reese Witherspoon as the lovable blonde-sorority-girl-turned-law-student who proves to her doubtful ex-boyfriend and all the other Harvard kids to be actually, like, really smart, is a perfect example of all of the girl power Rom-Coms released in the early 2000s. It’s smart, it’s quotable, and the outfits are downright iconic. There’s nothing high brow about it, it’s just pure, unadulterated fun. Just like the “Bend-and-Snap,” the film Legally Blonde works every time.–Annie Black
18. Major League
Year: 1989
Director: David S. Ward
Stars: Charlie Sheen, Tom Berenger, Corbin Bernsen, Margaret Whitton, James Gammon, Rene Russo, Wesley Snipes, Dennis Haysbert
Rating: R
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Many can laugh at this crazy cast of oddballs, but only a select few can look back and laugh. Because for those in Cleveland and northeastern Ohio, it’s all too real. Not until the second film’s release did the Cleveland Indians finally break out of their 30-year slump. Some will say it was the new stadium. Others, the even more superstitious ones (most baseball fans), may point to the dominance and swagger of Rick “Wild Thing” Vaughn, as portrayed by Charlie Sheen. (Fun fact: Sheen was actually a star pitcher in high school.) Whatever the case, the really bad times are in the past, and let’s hope, for the sake of another one of these movies popping up, they stay there. —Joe Shearer
19. SpaceballsYear: 1987
Director: Mel Brooks
Stars: John Candy, Rick Moranis, Bill Pullman, Joan Rivers, Mel Brooks, Daphne Zuniga
Genre: Comedy, Science Fiction & Fantasy
Rating: PG
Originally perceived as one of writer/director Mel Brooks’ lesser works, this loving send-up of the sci-fi/fantasy genre (specifically, Star Wars) has, over the years, wormed its way into the hearts of a new generation of fans catching it for the first time at home. “May the Schwartz be with you,” “Ludicrous Speed,” “Mawg”—if these are all terms that mean nothing to you then it’s high-time you checked this movie out and see what all the fuss is about. —Mark Rozeman
20. Down By Law
Year: 1986
Director: Jim Jarmusch
Stars: Tom Waits, John Lurie, Roberto Benigni, Ellen Barkin
Rating: R
What makes Down By Law the quintessential Jarmusch film is in the deliberate exclusion of a sequence most other directors would have turned into their calling card. Two innocent inmates (John Lurie and Tom Waits) are joined by a third prisoner (Roberto Benigni), who is guilty but has a pretty airtight argument for self-defense. While playing cards, they discuss various exciting prison break scenes in film history, which motivates Benigni’s character to mention that he has a foolproof plan of escape. After a scene that references such cinematic moments, Jarmusch directly cuts to the prisoners already running away from prison, having cut the escape sequence all together. Jarmusch succinctly demonstrates that he isn’t interested in action but is far more fascinated by the individual quirks and mannerisms of his characters, while the dialogue that references such other prison break films expresses how deeply American mainstream pop culture has defined a big part of his personality.—Oktay Ege Kozak
21. Dear White People
Year: 2014
Director: Justin Simien
Stars: Tyler James Williams, Tessa Thompson, Kyle Gallner, Teyonah Parris, Brandon P. Bell, Malcolm Barrett
Rating: R
While Dear White People anchors its perspective in the struggles of its black leads, it argues that racism is a universal issue—or that, at least, dealing with the implications of racism, rooting it out at its source, is a personal task for every single human being to undertake. Who hasn’t, at one point or another, felt like they didn’t fit in with their peers? Who doesn’t feel the tug of social pressure when they’re in school? These aren’t questions about racism, but they do inch us collectively closer to targeting the very deep-seated core of what it is that still makes racism so prevalent today. Simien stumbles in the third act thanks to an amalgam of plot complications (a stroke of simplicity could have smoothed over _Dear White People_’s landing), but maybe a diluted ending would have glossed over the truth at the film’s core: that race politics are more complex than pretty much any one of us realizes.—Andy Crump
22. American Splendor
Year: 2003
Directors: Robert Pulcini, Shari Springer Berman
Stars: Paul Giamatti, Hope Davis, Judah Friedlander, James Urbaniak
Rating: R
Harvey Pekar’s “American Splendor” books are fascinating: Pekar believed that even the most mundane and seemingly uncomplicated lives were worth documenting. American Splendor showcases this theory by combining real footage of Pekar, fictionalized versions of characters from his life—maintaining both stylized caricatures and naturalistic drama—and even animated segments pulled from the comics to create a cohesive whole that presents an ordinary life as a fascinating experience. —Ross Bonaime
23. Stranger Than Paradise
Year: 1984
Director: Jim Jarmusch
Stars: John Lurie, Eszter Balint, Richard Edson
Rating: R
Jarmusch has fashioned a wildly idiosyncratic, stylish and coherent body of work. In the early ’80s, right out of film school, Jarmusch inadvertently helped define the American independent movement when his second feature, Stranger Than Paradise, found an audience of people who enjoyed its hip-but-relaxed pace, deadpan humor and apparent awareness of world cinema. The film is stylistically simple, with even fewer shots than the film he made during school, Permanent Vacation, and it seemed to satisfy a hunger for movies that eschew Hollywood formula. That hunger didn’t go unnoticed by the industry, which has since created specialized subsidiaries of major studios, festivals like Sundance and cable channels that champion “independent” filmmakers.—Robert Davis
24. A Hard Day’s Night
Year: 1964
Director: Richard Lester
Stars: John Lennon, Paul McCartney, George Harrison, Ringo Starr, Wilfrid Brambell
Rating: G
That opening chord of “A Hard Day’s Night” is iconic on its own, but when it’s paired with scenes of the Fab Four gleefully outrunning a crowd of screaming fans? Forget about it. The first Beatles movie—a mockumentary filmed at the height of Beatlemania—also happens to be their best; it’s funny, silly, weirdly melancholy at times (it’s hard not to see the foreshadowing when Ringo temporarily quits the band after feeling unappreciated) and full of some fantastic early performances. It manages to poke fun at the fame machine from the inside, and we always get the sense that no one found it funnier than John, Paul, George and Ringo.—Bonnie Stiernberg
25. Sleepless in SeattleYear: 1993
Director: Nora Ephron
Stars Tom Hanks, Meg Ryan, Bill Pullman
Rating: PG
Sleepless in Seattle is essentially one giant love letter to 1957’s An Affair to Remember from writer/director Nora Ephron. Rita Wilson gives a memorable teary summary of the movie, and Annie (Meg Ryan) watches it before writing to Sam (Tom Hanks) inviting him to meet her at the top of the Empire State Building—the way Cary Grant and Deborah Kerr attempt to in their movie—on Valentine’s Day. When they finally meet on the observation deck, the theme from An Affair to Remember swells, setting the mood for anyone with an appreciation for good rom-coms. —Bonnie Stiernberg
26. City Lights
Year: 1931
Director: Charles Chaplin
Stars: Charles Chaplin, Virginia Cherrill, Harry Myers, Florence Lee
Rating: G
In his later years, Charlie Chaplin was known for bringing pathos into his comedy whenever he had the opportunity. City Lights is the movie where he earns every bit of it. While its structure resembles Chaplin’s usual picaresque format, there’s more of a deliberate purpose as the tramp tries to help a poor, blind flower girl, played adorably by Virginia Cherrill. Harry Myers also deserves a mention for his performance as the millionaire who’s generous when he’s drunk and can’t remember his good deeds when he’s sober. —Jeremy Mathews
27. Time Bandits
Year: 1981
Director: Terry Gilliam
Stars: John Cleese, Sean Connery, Shelley Duvall, Michael Palin, Katherine Helmond, Ian Holm
Rating: PG
The first in Terry Gilliam’s “Trilogy of Imagination,” Time Bandits breathes with the unfettered glee of cinematic magic. Told through the eyes of Kevin, a neglected 11 year-old (Craig Warnock), the film details a literal battle between Good and Evil, between God (Ralph Richardson) and the Devil (David Warner)—though they’re never explicitly referred to as such. What Gilliam accomplishes, as Kevin meets such luminaries as Robin Hood (John Cleese), Napoleon (Ian Holm) and an irrepressibly charming King Agamemnon (Sean Connery, of course), is the perfect ode to imagination, wherein a kid’s bedroom musings gain the seriousness and weight of world-shaking war. Like a much weirder step-cousin to Bill & Ted, Time Bandits employs nostalgia and pseudo-history in equal measure to capture, with boundless invention, what it feels like be 11 again.
28. The Gold Rush
Year: 1925
Director: Charlie Chaplin
Stars: Charlie Chaplin, Mack Swain, Tom Murray, Georgia Hale
Rating: NR
The Klondike gold rush made the perfect setting for Charles Chaplin’s tramp to run wild. Chaplin took all the motifs he could find from adventure novels, melodramas and other stories of the northern frontier, tossed them in a blender and served up a collection of what would become his most famous scenes. He finds humor in peril—with a suspenseful teetering cabin scene, as well as starvation (when he famously makes a meal of his boot) and of course finds time to show off with his dancing roll scene. However, no one has succeeded in finding any humor in the atrocious voiceover Chaplin added to the 1942 rerelease. Be sure to watch the original version. For a more serious take on the Klondike hardships, see Clarence Brown’s The Trail of ’98 (1928).
29. The Player
Year: 1992
Director: Robert Altman
Stars: Tim Robbins, Greta Scaachi, Fred Ward, Whoopi Goldberg
Rating: R
Robert Altman’s cameo-heavy Hollywood satire was rapturously received in 1992, and along with the next year’s Short Cuts it represents his late-career peak. Structured a bit like a film noir, albeit in the shallow, pampered world of movie executives, The Player’s mockery of the business gradually grows warmer until it seems to embrace the schmaltz and insincerity of Hollywood. It’s smart satire with a wicked bite and a couple of great performances from Robbins and Goldberg, and a bonus Burt Reynolds cameo for all you Gator fans.—Garrett Martin
30. Shiva Baby
Year: 2021
Director: Emma Seligman
Stars: Rachel Sennott, Molly Gordon, Polly Draper, Fred Melamed, Danny Deferrari, Dianna Agron
Rating: NR
Marvelously uncomfortable and cringe-inducingly hilarious, Emma Seligman’s Shiva Baby rides a fine line between comedy and horror that perfectly suits its premise—and feels immediately in step with its protagonist, the college-aged Danielle. Played by actress/comedian Rachel Sennott, already messy-millennial royalty by virtue of her extremely online comic sensibility, Danielle is first glimpsed mid-tryst, an unconvincing orgasm closing out her perfunctory dirty talk (“Yeah, daddy”) before she dismounts and collects a wad of cash from the older Max (Danny Deferrari). Though it’s transactional, as any sugar relationship tends to be, Danielle seems open to discussing her nebulous career aspirations with Max, and he gives her an expensive bracelet—suggesting a quasi-intimate familiarity to their dynamic, even if the encounter’s underlying awkwardness keeps either from getting too comfortable. As such, it’s a smart tease of what’s to come, as Danielle schleps from Max’s apartment to meet up with her parents, Debbie (Polly Draper) and Joel (Fred Melamed, naturally), and sit shiva in the home of a family friend or relative. That Danielle’s unclear on who exactly died is a recurring joke, and a consistently good one, but there’s little time to figure out the details before she’s plunged into the event: A disorienting minefield of small talk, thin smiles and self-serve schmear. You don’t have to be Jewish to appreciate the high anxiety and mortifying comedy of Seligman’s film, though it helps. Underneath all the best Jewish punchlines lies a weary acknowledgement of inevitable suffering; the Coen Brothers knew this in crafting A Serious Man, their riotous retelling of the Book of Job, and Seligman knows it in Shiva Baby. That the climax involves shattered glass, helpless tears and a few humiliations more marks this as one of the most confidently, winningly Jewish comedies in years.—Isaac Feldberg
31. Forgetting Sarah Marshall
Year: 2008
Director: Nicholas Stoller
Stars: Jason Segel, Kristen Bell, Mila Kunis, Bill Hader, Jack McBrayer, Paul Rudd, Jonah Hill
Rating: R
Following one of the standard romantic comedy tropes, a man (in this case played by Jason Segel) is tempted to chase the wrong girl (Kristen Bell), ignoring the soulmate (Mila Kunis) right in front him. But while we’d seen the set-up before, we’d seen nothing like Segal’s character Peter getting dumped while naked, Russell Brand as the lead singer for Infant Sorrow or Peter’s A Taste For Love Dracula-themed puppet-comedy-rock-opera. Everyone you’d expect (Jonah Hill, Paul Rudd, Kristen Wiig, Bill Hader) co-stars.—Josh Jackson
32. Spring BreakersYear: 2013
Director: Harmony Korine
Stars: Vanessa Hudgens, Selena Gomez, Ashley Benson, Rachel Korine, James Franco
Rating: R
Watching James Franco in _Spring Breakers_, one has to ask: Is this a put-on? But the scarier question is, What if it’s not? The brilliance of his portrayal of Alien, a Scarface-aspiring dirt-bag, is that no matter how outlandishly over-the-top it goes—“Look at my shit!”—there remains a deeply unsettling edge to the performance that suggests a white-trash nightmare who could do real damage to those around him. We laugh at Franco as Alien, but the laughs get stuck in our throat: Just like the movie, his performance is a wickedly satiric look at our worst impressions of youth culture—until it gets so frighteningly real that we’re left dazed and amazed.—Tim Grierson
33. Scott Pilgrim vs. the WorldYear: 2010
Director: Edgar Wright
Stars: Michael Cera, Mary Elizabeth Winstead, Brie Larson, Chris Evans, Alison Pill, Aubrey Plaza, Jason Schwartzman, Kieran Culkin
Rating: PG-13
In many ways, all of Edgar Wright’s films have been romantic comedies in some fashion. Shaun of the Dead just happens to have zombies and Hot Fuzz just happens to have two males as its romantic leads. In this way, Scott Pilgrim vs. The World is perhaps Wright’s most clear-cut attempt at a rom-com. The story deals in a situation that is all too familiar in the relationship world—that of dealing with your romantic partner’s past romantic baggage. However, to paraphrase Scott Pilgrim’s own words, this emotional baggage (i.e., his girlfriend’s evil ex-boyfriends) is actively trying to kill him every 30 seconds. Just as in a musical, where characters start singing when emotions run too high, Scott Pilgrim dishes out videogame-style duels whenever emotional conflict comes into play. As heightened as Scott Pilgrim may seem at times, its undertones are all too relatable. —Mark Rozeman
34. The Ruling Class
Year: 1972
Director: Peter Medak
Stars: Pete O’Toole
Rating: PG
Peter O’Toole is electrifying in this bitter satire of British social status and the treatment of mental health. The Ruling Class frequently switches tones with no warning—this the kind of movie where characters will occasionally break out into absurd songs despite not being a musical, but that also ends with a bleak final passage that is way more of a horror film than anything else. It’s not particularly subtle in its critique of capitalism and class structure, but satire doesn’t have to be subtle to be effective. O’Toole was nominated for an Oscar for this one, and it’s obvious why when you watch it.—Garrett Martin
35. Trainwreck
Year: 2015
Director: Judd Apatow
Stars: Amy Schumer, Bill Hader, Brie Larson, Colin Quinn, John Cena, Vanessa Bayer, Tilda Swinton, LeBron James, Mike Birbiglia
Rating: R
Think of Trainwreck as Amy Schumer’s comedy fed through Judd Apatow’s directorial dehydrator: It’s 124 minutes of everything we love about Schumer deprived of just enough bite and flavor to keep us tantalized, and not enough to make the experience special. To the credit of both Apatow and Schumer, who wrote the whole damn thing, they’ve made a funny film—and in fairness, “funny” is all that Trainwreck needs to be. When the picture clicks, you’ll be too busy bearing down and expelling laughter to catch any air or worry about politics. Schumer and her colossal supporting cast easily prove that all anyone needs to cut together a solid comedy is good old-fashioned chemistry, sharp delivery, and a surfeit of killer punchlines. —Andy Crump
36. Man Bites Dog
Year: 1992
Directors: Rémy Belvaux, André Bonzel, Benoît Poelvoorde
Stars: Rémy Belvaux, Benoît Poelvoorde, Andre Bonzel
Rating: NC-17
An undeniable forebear to Behind the Mask: The Rise of Leslie Vernon, Man Bites Dog won the International Critics’ Prize at the 1992 Cannes Film Festival, only to receive an NC-17 rating upon its US release, banned in Sweden altogether. One can understand the squeamishness: Man Bites Dog unflinchingly portrays serial murder in its graphic banality, victims ranging from children to the elderly to a gang-raped woman whose corpse is later photographed with her entrails spilling all over the table on which she was violated, the perpetrators lying in drunken post-revelry, heaped on the floor. Filmed as a mockumentary, Man Bites Dog goes to distressing lengths to portray the exigencies of murder as basely as possible, incorporating the reluctance of the crew filming such horrors to offer the audience a reflection of the ways they were probably reacting. The fascinated sorrow expressed by the documentary film’s director (Rémy Belvaux) as he realizes what making a documentary film about a serial killer actually means, becoming more and more complicit with the killings as the film goes on, explicitly points to our willingness as bystanders to stomach the horrors displayed. Still, we react viscerally while the film explores conceptual themes of true crime as pop culture commodity and reality TV as detrimental mitigation of truth, ultimately indicting viewers apt to enjoy this movie while simultaneously catering to them. Benoit (Benoît Poelvoorde), the subject of the faux film, is of course an incredibly intelligent societal outcast beset by xenophobia and misogyny, offering up countless neuroses to explore behind his psychopathy and serial murder, which he treats as a legitimate job. But Man Bites Dog is more about the ways in which we consume a movie like Man Bites Dog, concerned less about the flagrant killing it indulges for laughs than it is the laughs themselves, implying that the real blame for such well-known horror falls at our feet, in which each day we take big, basic steps to normalize the violence and hate that constantly surrounds us. —Dom Sinacola
37. The Beach Bum
Year: 2019
Director: Harmony Korine
Stars: Matthew McConaughey, Snoop Dogg, Isla Fisher, Martin Lawrence, Zac Efron, Jonah Hill
Rating: R
Witness Matthew McConaughey, transcending. Revel in it, because this has got to be as high as he goes. As Moondog, the opposite, arch nemesis perhaps, to the Matthew McConaughey of the Lincoln commercials—on TV the interstitial, nonchalant pool shark and connoisseur of fine leather everything, a man to whom one whispers courteously, in reverence between network shows—Matthew McConaughey realizes the full flat circle of his essence. The actor bears multitudes, and they all converge upon the befuddled Moondog, consummate inhuman and titular hobo of the southern sands of these United States. One could claim that Moondog’s hedonism represents a moral imperative to consume all that’s truly beautiful about life, and Moondog says as much even if he’s plagiarising D.H. Lawrence (which he admits to his best friend Lingerie, who’s carried on a long-time affair with Moondog’s wife, and who’s played by Snoop Dog in a career best performance). Speaking of Lawrence, Martin also gives a career-best performance as Captain Wack, dolphin lover; the film slides effortlessly into absurdity. One could claim, too, that Moondog’s little but a self-destructive addict somehow given a free pass to circumvent basic human responsibility altogether. One could claim that director Harmony Korine doesn’t believe in basic human responsibility anyway. He doesn’t claim much in the way of explicating Moondog’s whole way of being, doesn’t reserve any judgment for the man’s mantra and blissful lurch towards oblivion. Or annihilation. The uniform for which is casual, including JNCO jeans, brandished by Flicker (Zac Efron), with whom Moondog escapes the court-mandated rehab that seemingly does nothing to pierce the armor of intoxication Moondog’s spent his life reinforcing. Whether he’s protecting himself from any serious human connection or from the crass hellscape of capitalistic society—whether he’s deeply grieving a tragedy that occurs halfway through The Beach Bum, Harmony Korine’s masterpiece of feeling good in the face of feeling the worst, or avoiding all feeling completely—he’s still a bad dad. Or he’s an artist. Or a saint. Or he’s from a different dimension, as his wife (Isla Fisher) explains to their daughter, as she most likely always has, against a breathtaking vista followed not long after by a heartbreaking sunset, both photographed by Benoît Debie, in Miami of all places, all magnificent and hollow, the film a hagiography for the end of history. —Dom Sinacola
38. Observe and Report
Year: 2009
Director: Jody Hill
Stars: Seth Rogen, Ray Liotta, Michael Peña, Anna Faris, Jesse Plemons, Colette Wolfe
Rating: R
In 2009 comedy fans bought tickets for Observe and Report expecting Seth Rogen’s lovable stoner man-child schtick. Instead they had to confront the ugly, violent dark comedy that director Jody Hill perfected with his HBO shows Eastbound & Down and Vice Principals. Rogen is surprisingly good in a role that seems written for Danny McBride, a seething cocktail of confusion, depression, arrogance and anger. Anna Faris, Aziz Ansari, Michael Pena and a young Jesse Plemons round out a strong cast.–Garrett Martin
39. Baby Mama
Year: 2008
Director: Michael McCullers
Stars: Tina Fey, Amy Poehler, Greg Kinnear, Dax Shepard, Sigourney Weaver
Rating: PG-13
Baby Mama is not great. If you can get past the disappointment felt in the wake of high expectations for Tina Fey and Amy Poehler’s first big screen team-up, though, you’ll find a piece of Hollywood product that’s just charming enough to be worth your time. Fey and Poehler help elevate hit and miss material, and Steve Martin revives some of his early career absurdity in a great supporting role. It’s still not what we were hoping it would be back in 2008, but it’s far from a disaster.–Garrett Martin
40. Schizopolis
Year: 1996
Director: Steven Soderbergh
Stars: Steven Soderbergh, Dave Jensen, Betsy Brantley, Eddie Jemison
Rating: R
Everything and nothing at all, Schizopolis came about in the midst of a prolific period for Steven Soderbergh—though one could say that for practically any movie he’s made throughout his career. Released the same year as Gray’s Anatomy, and on the heels of King of the Hill and The Underneath, one an award-winning bildungsroman and the latter a remake of a Robert Siodmak noir, Schizopolis puts something of a cap on the notion of Soderbergh as auteur. Here he seems capable of making any kind of movie he wants to make—this time a largely improvised experimental comedy shot on a quick-and-dirty microbudget, pretty much between breakfast and dinner. And, as further testament to Soderbergh’s weird pandextrousness, Schizopolis feels inextricably of its time, mapping in broad, absurd strokes the way meaningful communication has become a lost privilege of a technologically advancing society. As Soderbergh himself (who also stars) states in a prelude to the actual film: “In the event that you find certain sequences or ideas confusing, please bear in mind that this is your fault, not ours.” As a director in full control of even his most tossed-off films, he’s probably right. —Dom Sinacola
