The 50 Best Comedies on HBO Max Right Now (May 2021)

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The 50 Best Comedies on HBO Max Right Now (May 2021)

Can a streaming service have too much content?

Probably not, but HBO Max is determined to find out. Warner’s streamer has an overwhelming variety of movies, cartoons and TV shows from the last century of entertainment, and although I love that as a customer, it’s beyond daunting as a guy whose job involves making lists of the stuff you can stream on services like this. But after poring over the hundreds of movies currently available through HBO Max, I’ve been able to strip it down to the 50 funniest, and you can find those results below.

As far as comedy movies goes, HBO Max has the best, deepest, and most varied selection of any streamer at the moment. Good luck finding this many classics or pre-’90s comedies on the other services. HBO 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 50 funniest movies on HBO Max today.

1. Walk Hard: The Dewey Cox Story

walk-hard-poster.jpg
Year: 2007
Director: Jake Kasdan
Stars: John C. Reilly, Jenna Fischer, Raymond J. Barry, Kristen Wiig, Tim Meadows, Margo Martindale
Rotten Tomatoes Score: 74%
Rating: R
Runtime: 96 minutes

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Although Walk Hard: The Dewey Cox Story claims to be a spoof of biopics and their extreme depictions of artists—especially musicians—biopics’ exaggerations are a reflection of the frailties and eccentricities of the artists which they profile, so it’s hard to distinguish a satire about biopics from a satire about musicians. Regardless of what category the film falls into, Walk Hard does not really tow the fine line of being clever so much as it provides a fun and absurd romp with heaps of laughs. John C. Reilly, who plays rising and troubled music star Dewey Cox, skillfully presents a dopey-yet-conniving and shallow-but-sincere character with a heart of fool’s gold. Looking something like Johnny Cash crossed with Tom Waits, Cox has multiple addictions, wives and musical phases. Aspiring to a level beyond greatness after he accidentally kills his brother by splitting him in half with a machete when they are young boys growing up in Alabama, Cox is compelled to compensate for the loss of his brother, leading to a life of excess and indulgence. But Reilly isn’t the only star of the film. Kristen Wiig shines as Cox’s frustrated wife and the mother of their seemingly infinite amount of children; as Cox’s other frustrated wife and duet partner, Jenna Fischer is superb. Tim Meadows is hysterical with a stand out performance as Cox’s bandmate who can’t seem to stop doing or introducing Cox to increasingly heavy drugs. Additionally, cameos from Jack White (Elvis Presley), Jack Black (Paul McCartney), Paul Rudd (John Lennon), Jason Schwartzman (Ringo Starr), Justin Long (George Harrison), Eddie Vedder, Jackson Browne and Lyle Lovett make the film even more ridiculous. Like most films of its ilk, Walk Hard may go too over-the-top to prove itself, but there is something charming about it, underscored by its genuine love of music and affinity for musicians. It is also obvious from one of the first lines in the film (“Guys, I need Cox!”) that this project neither takes itself too seriously nor asks the same of its viewers. —Pamela Chelin



2. Best in Show

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Year: 2000
Director: Christopher Guest
Stars: Eugene Levy, Catherine O’Hara, Christopher Guest, Parker Posey, Jennifer Coolidge, Jane Lynch, Michael Hitchcock, John Michael Higgins, Michael McKean, Bob Balaban, Ed Begley Jr., Fred Willard
Rotten Tomatoes Score: 94%
Rating: PG-13
Runtime: 91 minutes

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The genius of Christopher Guest’s particular style of mockumentary is in his cast’s complete commitment to character, and none of his films are inhabited by a more hilarious ensemble than Best in Show. Parker Posey and Michael Hitchcock as Meg and Hamilton Swan project their own neuroses on their poor Weimaraner. Eugene Levy’s Gerry Fleck is outrageously outmatched by his wife Cookie, played by Catherine O’Hara—the secret weapon of most Guest films. The director himself plays Harlan Pepper, a Southern gentleman with no self-awareness and an ability to name all kinds of nuts. The more inane his rambling gets, the harder it is to keep from laughing. Finding the ridiculousness in something like the world of dog shows might not be difficult, but there’s no mocking tone to the subject, just to the quirks of human nature. The improvisation and dead-pan delivery from Jane Lynch, Bob Balaban, Jennifer Coolidge, Michael McKean and especially Fred Willard as the sports announcer who knows nothing about the subject he’s paid to talk about, elevate the medium by giving surprising dimension to their characters. It’s a symphony of creation from a troupe of performers at their peak. —Josh Jackson



3. This Is Spinal Tap


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Year: 1984
Director: Rob Reiner
Stars: Christopher Guest, Michael McKean, Harry Shearer, Rob Reiner
Rotten Tomatoes Score: 95%
Rating: R
Runtime: 82 minutes

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The only rock documentary worth watching, according to Kurt Cobain and Dave Grohl—next to Pennebaker’s Dont Look BackThis Is Spinal Tap isn’t really a documentary at all, though it aspires to so much more truth than any countless, beatific biopic that’s come out in the past couple decades or so. The story of a fictional metal/cock rock band told through talking head interviews that chronicle their iconic ups and downs, Spinal Tap is our best, early glimpse at the team who’d go on to make Waiting for Guffman, A Mighty Wind and Best in Show. While it isn’t the first of its kind, it feels like it could be: So deeply does it understand the world it parodies, Spinal Tap knows that a mockumentary is best a biopic of people who never existed, taking the personalities that define this starfucking realm and then, ever so slightly, ever so lovingly, cranking them to 11. —Dom Sinacola



4. The Great Dictator

chaplin_Great_dictator.jpg
Year: 1940
Director: Charles Chaplin
Stars: Charles Chaplin, Paulette Goddard, Jack Oakie, Reginald Gardiner
Rotten Tomatoes Score: 93%
Rating: G
Runtime: 126 minutes

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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



5. The Philadelphia Story

philadelphia_story_poster.jpg
Year: 1940
Director: George Cukor
Stars: Katharine Hepburn, Cary Grant, James Stewart, Ruth Hussey, John Howard
Rotten Tomatoes Score: 100%
Rating: NR
Runtime: 112 minutes

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Can you believe there was a time when Katharine Hepburn was known in Hollywood as “box office poison”? This adaptation of a Broadway hit was a vehicle to get her career back on track after a series of flops. Her performance as icy heiress Tracy Lord in this “remarriage” comedy is a force of nature. Happily, her no-longer-drunken ex is played by Cary Grant, who is a fabulous foil. Jimmy Stewart and Ruth Hussey round out the cast as reporters in not-so-clever disguise. Pretty much everything about this movie is a pure delight, and the script is a masterpiece. —Amy Glynn



6. Caddyshack

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Year: 1980
Director: Harold Ramis
Stars: Chevy Chase, Rodney Dangerfield, Ted Knight, Bill Murray, Michael O’Keefe
Rotten Tomatoes Score: 73%
Rating: R
Runtime: 98 minutes

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There are four faces on that poster to the left, and all of them are equally crucial to Caddyshack’s enduring popularity. From Ted Knight’s aristocratic bluster, to Rodney Dangerfield’s irreverent populism, to the glib playboy Chevy Chase, to Bill Murray’s iconic idiot, Caddyshack has one of the greatest casts of any comedy in memory. Add in a sharp script from National Lampoon co-founder Doug Kenney and amiably shaggy direction from Harold Ramis, and you have an all-time classic.—Garrett Martin



7. The Graduate


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Year: 1967
Director: Mike Nichols
Stars: Dustin Hoffman, Anne Bancroft, Katherine Ross, William Daniels
Rotten Tomatoes Score: 87%
Rating: R
Runtime: 105 minutes

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In the undisputed king of movies for those headed out into the real world, a hyper-accomplished recent grad (Dustin Hoffman) panics at the prospect of his future and falls into an affair with the much older wife of his father’s business partner (Anne Bancroft). It helped define a generation long since embalmed by history, but the sense of longing for an alternative hasn’t aged. —Jeffrey Bloomer



8. Shaun of the Dead

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Year: 2004
Director: Edgar Wright
Stars: Simon Pegg, Kate Ashfield, Lucy Davis, Nick Frost, Dylan Moran, Bill Nighy
Rotten Tomatoes Score: 92%
Rating: R
Runtime: 97 minutes

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Together, 28 Days Later and Shaun of the Dead established precedents for the “modern” zombie film that have more or less continued to this day. The former made “zombies” scary again, and the latter showed that the cultural zeitgeist of zombiedom (which was picking up around this point) could be mined for huge laughs as well. Most importantly, the two types of films could exist side by side. Shaun of the Dead makes a wry, totally valid criticism of modern, digital, white-collar life through its wonderful build-up and tracking shots, which show slacker Shaun wandering his neighborhood failing to even realize that a zombie apocalypse has happened. Once he and his oaf of a friend finally realize what’s happening and take up arms to protect their friends and loved ones, the film becomes a fast-paced, funny and surprisingly emotional action-comedy. Few horror comedies have actually combined the elements of humor and serious horror the way this one does in certain scenes—just go back and watch the part where David is dragged through the window of The Winchester by zombies and literally torn to pieces. It’s a film that works on so many levels, and manages to be uproariously funny while still being quite faithful to the fidelity of Romero-style zombies. Much in the same way as Zombieland (a definite spiritual successor), it shows that whether the zombies are “scary” is ultimately a matter of how everyone reacts to them. Shaun of the Dead was so momentous that it’s next to impossible to make a zombie comedy at this point without being accused of ripping it off—take Fido, a film that seems based entirely on the “domesticated zombie” gag at the end of this film. —Jim Vorel



9. Waiting for Guffman

waiting_for_guffman_poster.jpg Year: 1996
Director: Christopher Guest
Stars: Christopher Guest, Eugene Levy, Catherine O’Hara, Parker Posey, Bob Balaban, Fred Willard, Larry Miller, Paul Benedict
Rotten Tomatoes Score: 91%
Rating: R
Runtime: 84 minutes

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The first of Christopher Guest’s mockumentaries co-written with Eugene Levy, Waiting for Guffman introduced the world to a cast that would form the backbone of their other projects. The film picked up on This is Spinal Tap’s tradition while bringing a decidedly sweeter tone to the table. Corky St. Clair leads the lovable bunch of misfits who comprise the small-town theater group. They are determined to catch the eye of Broadway producer Mort Guffman, as they put on a play about their town’s history, Red, White and Blaine. Needless to say, things go wrong in all the right ways. —Amanda Wicks



10. Modern Times

modern-times.jpg Year: 1936
Director: Charles Chaplin
Stars: Charles Chaplin, Paulette Goddard, Henry Bergman
Rotten Tomatoes Score: 100%
Rating: G
Runtime: 88 minutes

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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



11. The Thin Man

the_thin_man_poster.jpg Year: 1934
Director: W. S. Van Dyke II
Stars: William Powell, Myrna Loy, Maureen O’Sullivan, Nat Pendleton, Minna Gombell, Porter Hall
Rotten Tomatoes Score: 98%
Rating: NR
Runtime: 93 minutes

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Sequels are far from a recent development. Hollywood pumped out six movies in the ‘30s and ‘40s starring William Powell and Myrna Loy as the bantering sleuths Nick and Nora Charles. The first—and maybe the best—of them is 1934’s The Thin Man, where the retired detective and his heiress wife investigate a murder in between bon mots and many, many cocktails. The Thin Man is a sterling example of the slick, high society confections that Hollywood excelled at during the Depression, and Nick and Nora have influenced pretty much every hyper-verbal cinematic couple that followed.—Garrett Martin



12. Pee-Wee’s Big Adventure

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Year: 1985
Director: Tim Burton
Stars: Paul Reubens, E.G. Daily, Mark Holton, Diane Salinger, Jan Hooks, Cassandra Peterson
Rotten Tomatoes Score: 87%
Rating: PG
Runtime: 90 minutes

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Tim Burton’s full-length directorial debut is also one of his best. Pee-wee’s Big Adventure brings us into the bizarro world of Pee-wee Herman, the excitable, ageless protagonist that’s hopelessly attached to his bike. After it’s stolen in broad daylight, we see Herman travel across the U.S. to reclaim his baby. And through the adventure and its ongoing discoveries (who knew the Alamo didn’t have a basement?) we’re introduced to unforgettable characters like Herman; his (sort-of) love interest, Dottie; the horrifying trucker ghost Large Marge; the snotty, rich Francis; and Herman’s dog, Speck. Herman’s wacky world is fully realized through the eye of Burton, and this one stands alone as a film that kids and adults can both get a kick out of.—Tyler Kane



13. Hot Fuzz


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Year: 2007
Director: Edgar Wright
Stars: Simon Pegg, Nick Frost, Jim Broadbent, Paddy Considine, Timothy Dalton, Olivia Colman
Rotten Tomatoes Score: 91%
Rating: R
Runtime: 121 minutes

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The second chapter in the Three Flavours Cornetto trilogy (before there was ever such a thing), Hot Fuzz is clear evidence that Edgar Wright is capable of anything. A blockbuster action flick, a thriller, a pulp plot, a winking noir, a commentary on classism in an increasingly urbanized society—the movie is all of these things, down to the marrow of its very existence. Moreso than Shaun of the Dead or The World’s End, Hot Fuzz inhabits its influences with the kind of aplomb to which any cinephile can relate: Somewhere between fascination, revulsion and pure visceral joy there walks the Michael Bays, the Don Simpsons, the John Woos, the Jerry Bruckheimers, and Wright gives each stalwart his due. Plus, he does so with total respect, showing that he understands their films inside and out. And in that intimate knowledge he knows even better that filmmaking is a conflagration: Best to burn it all down and see what remains than build it from the ground up. —Dom Sinacola



14. When Harry Met Sally

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Year: 1989
Director: Rob Reiner
Stars: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby
Rotten Tomatoes Score: 90%
Rating: R
Runtime: 96 minutes

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Easily the most beloved romantic comedy of its decade, the story of Harry (Billy Crystal), Sally (Meg Ryan) and their 12-year journey to couple-hood boasts a solid script by Nora Ephron that feeds and feeds off of the unexpected chemistry between its leads. (And with each new generation of lovers watching the diner scene for the first time, another woman laughs and another man sits silently, wondering what’s so funny.) —Michael Burgin



15. Women on the Verge of a Nervous Breakdown

women_on_the_verge_poster.jpg Year: 1988
Director: Pedro Almodóvar
Stars: Carmen Maura, Antonio Banderas, Julieta Serrano, María Barranco, Rossy de Palma, Fernando Guillén
Rotten Tomatoes Score: 90%
Rating: R
Runtime: 88 minutes

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Women on the Verge of a Nervous Breakdown put Spanish director Pedro Almodóvar on the international map. Part melodrama, part dark-yet-screwball comedy, the film tells the story of Pepa (Carmen Maura), whose suicide attempt is interrupted, with bizarre and hilarious consequences, Almodóvar mounting an investigation of the human, and particularly female, psyche. A rivetingly directed ensemble cast (including Antonio Banderas) and lush visual style make this film every bit as compelling as it was in 1988. —Amy Glynn



16. Happy Gilmore

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Year: 1996
Director: Dennis Dugan
Stars: Adam Sandler, Christopher McDonald, Julie Bowen, Frances Bay, Carl Weathers
Rotten Tomatoes Score: 61%
Rating: PG-13
Runtime: 92 minutes

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Adam Sandler could’ve retired in 1998, after his first three movies, and his comedy legacy would’ve been secured. (He maybe should’ve retired then, but let’s not get into that.) It’s hard to pick between The Wedding Singer, Billy Madison and Happy Gilmore, but let’s talk about that last one right now. The tale of a failed hockey player becoming a champion golfer is an ideal vehicle for Sandler’s inchoate frat boy rage, and the absurd streak that elevated Madison above most Hollywood comedies of the day is even more visible here. It has some of the same problems as most Sandler movies—an underwritten, unbelievable love interest (here played by Modern Family’s Julie Bowen), a bare bones story that’s little more than a launching pad for jokes—but Gilmore is an ideal character for Sandler, and a great supporting cast (including Carl Weathers, Ben Stiller, Richard Kiel, Joe Flaherty, and Christopher McDonald as the iconic villain Shooter McGavin) help turn this into a legitimate classic. Also there’s a great chance this is the main thing younger people know Bob Barker from, which is actually kind of sad.—Garrett Martin



17. Safety Last!

safety-last-poster.jpg Year: 1923
Directors: Fred C. Newmeyer, Sam Taylor
Stars: Harold Lloyd, Mildred Davis, Bill Strother
Rotten Tomatoes Score: 97%
Rating: NR
Runtime: 80 minutes

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“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. —Jeremy Mathews



18. Gremlins 2: The New Batch

gremlins-2-movie-poster.jpg Year: 1990
Director: Joe Dante
Stars: Zack Galligan, Phoebe Cates, John Glover, Robert Prosky
Rating: PG-13
Runtime: 107 minutes

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Joe Dante didn’t want to make a sequel to Gremlins. The first film exhausted him and was wrapped up so nicely, he didn’t see a need to carry the story forward. The studio, however, refused to give up and, out of desperation, gave him complete creative control. They sure got what they paid for, as the cult classic sequel throws absolutely everything at the viewer with zero interest in whether it will stick or not. It’s a slapstick comedy wrapped up in cartoonish violence and some sharp-edged satire about corporations and capitalism. Oh, and there’s a cameo by Hulk Hogan to boot. —Robert Ham



19. House

house.jpg Year: 1977
Director: Nobuhiko Obayashi
Stars: Kimiko Ikegami, Miki Jinbo, Kumiko Ohba
Genre: Comedy, Horror
Rotten Tomatoes Score: 90%
Rating: NR
Runtime: 88 minutes

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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



20. Midnight Run

midnight_run_poster.jpg Year: 1988
Director: Martin Brest
Stars: Robert De Niro, Charles Grodin, Yaphet Kotto, Dennis Farina, John Ashton
Rotten Tomatoes Score: 94%
Rating: R
Runtime: 122 minutes

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The ’80s created the textbook action/comedy formula, and director Martin Brest was smack dab in the middle of it. His Beverly Hills Cop was originally written as a straight action movie, until Eddie Murphy was cast in the lead role. Instead of keeping the overall self-serious tone of the film and just inserting some out-of-place comedy set pieces into the narrative, Murphy and Brest infused a lighthearted tone across the entire project, while keeping the basic requirements of an action structure in place. Midnight Run, Brest’s follow-up to Beverly Hills Cop, perfects this fusion. None of the action sequences take themselves too seriously, and none of comedy comes across as mugging, desperate to extract easy chuckles. The premise and structure are very simple and fairly predictable: It’s a traditional road movie wherein a grizzled bounty hunter (Robert DeNiro) has to transport a mob accountant (Charles Grodin) across the country, with the mob and the police squarely on their tail. What makes Midnight Run still feel fresh after 30 years is Brest’s aforementioned handle on tone, and the terrific chemistry between DeNiro and Grodin, so on point it’s surprising they weren’t reunited for other similar flicks after this. Usually the rough masculine bounty hunter would be the wild card against the accountant’s stuffy straight man, yet DeNiro and Grodin find refreshing ways of tinkering with that formula, with DeNiro’s character eventually coming across as a regular good guy who was dealt more than a few bad hands, and Grodin as a lovable but sometimes infuriating weirdo. —Oktay Ege Kozak



21. Billy Madison

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Year: 1995
Director: Tamra Davis
Stars: Adam Sandler, Darren McGavin, Bridgette Wilson-Sampras, Bradley Whitford, Norm MacDonald
Rotten Tomatoes Score: 42%
Rating: PG-13
Runtime: 89 minutes

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There’s a strong case to be made that Billy Madison is the best Adan Sandler movie. Sure, it’s not as human as The Wedding Singer, and it’s hard to vote against Happy Gilmore, but Madison so thoroughly exceeded the abominably low expectations I had for it in 1995 that it wound up being one of the most memorable movies of the decade. It’s still hilarious today, a perfect vehicle for Sandler’s man-child persona, and one that surrounds him with a fantastic supporting cast, including Bradley Whitford, Darren McGavin, Norm Macdonald, Chris Farley, and a giant penguin, among others. It’s not the story or even the jokes that make Billy Madison so funny—it’s the surreal flourishes, the way lines are delivered, how Tamra Davis (both a woman and an outsider to the small circle of men who have directed most of Sandler’s movies since) is able to contrast Sandler’s weirdness with a world that feels recognizable in its everyday mundanity. Later Sandler movies feel lazy and untethered from the real world, but Madison doesn’t suffer from either flaw. It’s dumb comedy done with enough weirdness and intelligence to become a true classic.—Garrett Martin



22. City Slickers

city-slickers.jpg Year:
Director: Ron Underwood
Stars: Billy Crystal, Daniel Stern, Bruno Kirby
Rotten Tomatoes Score: 88%
Rating: PG-13
Runtime: 114 minutes

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If you’re like me, City Slickers falls into the category of movies you liked when they came out, but you’re not sure if they hold up. Are the jokes dated? Were they funny when I was 22, but not so much now? Well, rest easy. Sure, there are a few jokes that might be a little juvenile and Billy Crystal’s shtick is a tad over the top now and then, but for the most part, this is a film with a well-crafted screenplay and actors who know when to improvise to great effect. Daniel Stern reminds one why he’s one of the best (and most underused) comedic actors around (the birthday party scene is side-splittingly funny), and the late Bruno Kirby (whose life was tragically cut short at 57 due to Leukemia) was simply one of the most versatile actors of his generation. —Michael Burgin


23. Metropolitan

Metropolitan_movie_poster.jpg
Year: 1990
Director: Whit Stillman
Stars: Carolyn Farina, Edward Clements, Chris Eigeman, Taylor Nichols, Allison Parisi, Dylan Hundley
Rotten Tomatoes Score: 93%
Rating: PG-13
Runtime: 98 minutes

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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



24. Down By Law

down_by_law_poster.jpg
Year: 1986
Director: Jim Jarmusch
Stars: Tom Waits, John Lurie, Roberto Benigni, Ellen Barkin
Rotten Tomatoes Score: 87%
Rating: R
Runtime: 107 minutes

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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



25. The Cable Guy


the_cable_guy_poster.jpg Year: 1996
Directors: Ben Stiller
Stars: Matthew Broderick, Jim Carrey, Leslie Mann, Jack Black, George Segal
Rotten Tomatoes Score: 53%
Rating: PG-13
Runtime: 91 minutes

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Ben Stiller’s dark comedy was a flop in ‘96, but it’s become a minor cult classic over the years due to its subversive wit and post-modern satire of television’s influence on the culture. At first Carrey seems like he’s in the wrong movie—his over-the-top schtick and ostentatious character decisions stick out in a movie that’s otherwise fairly subdued and full of ‘90s alt-comedy faves (like half of the Mr. Show cast pops up throughout)—but ultimately his gung ho approach fits both his character and the movie’s broader message about how TV’s first three decades effectively warped the sensibility of an entire generation. Also, it has one of Bob Odenkirk’s very best yelling scenes, which should make it an instant must-watch for all discerning viewers.—Garrett Martin




26. American Splendor

american-splendor.jpg Year: 2003
Directors: Robert Pulcini, Shari Springer Berman
Stars: Paul Giamatti, Hope Davis, Judah Friedlander, James Urbaniak
Rotten Tomatoes Score: 94%
Rating: R
Runtime: 100 minutes

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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



27. The Longest Yard

the_longest_yard_netflix.jpg Year: 1974
Director: Robert Aldrich
Stars: Burt Reynolds, Eddie Albert, Ed Lauter, Michael Conrad
Rotten Tomatoes Score: 79%
Rating: R
Runtime: 125 minutes

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It goes without saying that we’re talking about the original version of the film starring Burt Reynolds, not Adam Sandler’s 2005 debacle of a remake. Paul Crewe is an ex-football-player-turned-convict who fills the classic role of an inmate/protagonist who is initially despised by his fellow prisoners but ends up winning their favor. He leads a football team of inmates against the team of guards whom Crewe refused to coach. Not often are comedies set inside a jailhouse, but it works with The Longest Yard.—Paste Staff



28. A Christmas Story

A_Christmas_Story_film_poster.jpg Year: 1983
Directors: Bob Clark
Stars: Peter Billingsley, Darren McGavin, Melinda Dillon, Ian Petrella, Scotty Schwartz, R.D. Robb
Rotten Tomatoes Score: 89%
Rating: PG
Runtime: 93 minutes

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To wring something as genuinely warm and heartfelt as it is hilarious from a central theme of rampant consumerism is a rare thing. To supplant Christmas Day TV scheduling previously reserved only for classics like It’s a Wonderful Life and Miracle on 34th Street is quite another. Director Bob Clark assembles a pool of onscreen talent who were clearly born to inhabit Jean Shepherd’s treasured story of childhood amidst Major Awards, first swear words, cynical Mall Santas, and—of course—the ruminations on what it truly means to shoot your eye out. —Scott Wold



29. Dumb and Dumber

dumb_and_dumber_poster.jpg Year: 1994
Director: Peter and Bobby Farrelly
Stars: Jim Carrey, Jeff Daniels, Lauren Holly, Teri Garr, Karen Duffy, Mike Starr
Rotten Tomatoes Score: 68%
Rating: PG-13
Runtime: 106 minutes

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There is a special brand of nihilism at play in the Farrelly Brothers’ debut, one which vaunts stupidity above all else, not because the Farrellys want to celebrate being dumb over being smart, but because they seem to find no real consequences in the kind of ignorance inhabited by Lloyd (Jim Carrey, beloved) and Harry (Jeff Daniels, best role of his career) to the extent that morality for these characters is moot. Devoid of the brain power required to fully comprehend the vast world around them, operating on little more than teenage horniness and threats of unemployment (plus the image of a decapitated parakeet), Harry and Lloyd blissfully become involved in a kidnapping caper concerning the husband of wealthy heiress Mary Swanson (Lauren Holly). It works out as one might expect—in that it doesn’t work out, and that doesn’t matter—but not without developing a lot to love in these two dipshits, making its sequel feel unrelentingly mean-spirited by comparison. It shouldn’t be surprising then that pretty much every other Farrelly movie (sans There’s Something About Mary) has aged poorly: America doesn’t need any more movies that seem to actually honor our dumbest assholes. —Dom Sinacola



30. Down and Out in Beverly Hills

down_and_out_poster.jpg Year: 1986
Director: Paul Mazursky
Stars: Nick Nolte, Richard Dreyfuss, Bette Midler, Little Richard, Tracy Nelson, Elizabeth Peña
Rotten Tomatoes Score: 79%
Rating: R
Runtime: 103 minutes

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Anyone who’s seen a handful of Jean Renoir films will attest to the famous auteur’s fascination with examining unfair class structures, mocking the bourgeoisie all the while. And Boudu Saved from Drowning is an underseen work from Renoir that covers his favorite themes with a slightly lighter tone from, say, The Rules of the Game, about a well-to-do family rescuing a drowning vagrant (Michel Simon) and growing fond of him, enough to “civilize” him into becoming part of the bourgeoisie. Co-writer/director Paul Mazursky takes Renoir’s biting but levelheaded comedy and turns it into a bug-eyed, mocking satire about the vast class and income inequality in Los Angeles, a city that’s become even more ravaged by the gap between the rich and poor since the remake’s release in 1986. The well-meaning but clueless rich family in the original turn into raging narcissists played spectacularly by Bette Midler and Richard Dreyfuss. Simon’s lovable Chaplin-like tramp in the French version is turned into Nick Nolte’s raving, drunken, sometimes incomprehensible bum. Down and Out in Beverly Hills isn’t necessarily a better film than Boudu, but the stark difference in tonal and satirical approach make them different enough experiences to warrant such a solid remake.—Oktay Ege Kozak



31. 13 Going on 30

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Year: 2004
Director: Gary Winick
Stars: Jennifer Garner, Mark Ruffalo, Judy Greer, Andy Serkis, Kathy Baker
Rotten Tomatoes Score: 79%
Rating: PG-13
Runtime: 97 minutes

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What could’ve been easily dismissed as a shameless Big ripoff might be even better than that Tom Hanks classic. Jennifer Garner is at her most charming as a 13-year-old in a grown-up’s body, and perennially underrated Judy Greer shines in her finest film role as Garner’s best frenemy. The gently nostalgic script might deserve the most credit, though—a movie like this could have been ruined by lethal levels of cheese, but 13 Going on 30 has the exact right amount of crowd-pleasing schmaltz. —Allyn Moore



32. Desperately Seeking Susan

desperately_seeking_susan_poster.jpg Year: 1985
Director: Susan Seidelman
Stars: Rosanna Arquette, Madonna, Aidan Quinn, Mark Blum, Robert Joy, Laurie Metcalf
Rotten Tomatoes Score: 83%
Rating: PG-13
Runtime: 104 minutes

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At the height of her mid ‘80s ubiquity Madonna made an auspicious jump into acting with Desperately Seeking Susan, a cool, pleasant trifle about a bored suburban housewife (Rosanna Arquette) who tries to live vicariously through Madonna’s bohemian Susan before becoming directly entangled in her life. Despite various antics involving stolen ancient jewelry and shady mobsters, Susan is a pleasant, low-key snapshot of a long-gone New York. Look for cameos from Steven Wright, John Turturro and Giancarlo Esposito, along with a who’s who of Lower East Side musicians and performers, including Richard Hell, Ann Magnuson, John Lurie, Richard Edson, Annie Golden and Arto Lindsay.—Garrett Martin



33. Stranger Than Paradise

stranger_than_paradise_poster.jpg Year: 1984
Director: Jim Jarmusch
Stars: John Lurie, Eszter Balint, Richard Edson
Rotten Tomatoes Score: 96%
Rating: R
Runtime: 90 minutes

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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



34. A Hard Day’s Night

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Year: 1964
Director: Richard Lester
Stars: John Lennon, Paul McCartney, George Harrison, Ringo Starr, Wilfrid Brambell
Rotten Tomatoes Score: 98%
Rating: G
Runtime: 87 minutes

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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



35. City Lights

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Year: 1931
Director: Charles Chaplin
Stars: Charles Chaplin, Virginia Cherrill, Harry Myers, Florence Lee
Rotten Tomatoes Score: 98%
Rating: G
Runtime: 90 minutes

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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



36. Time Bandits

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Year: 1981
Director: Terry Gilliam
Stars: John Cleese, Sean Connery, Shelley Duvall, Michael Palin, Katherine Helmond, Ian Holm
Rotten Tomatoes Score: 89%
Rating: PG
Runtime: 110 minutes

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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.



37. Bill and Ted’s Excellent Adventure / Bill and Ted’s Bogus Journey

movie poster bill and ted.jpg 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
Rotten Tomatoes Score: 81% / 57%
Rating: PG
Runtime: 90 minutes / 98 minutes

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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




38. Babe: Pig in the City

babe-pig-in-the-city-movie-poster.jpg Year: 1998
Director: George Miller
Stars: James Cromwell, Elizabeth Daily, Magda Szubanski, Mickey Rooney, Mary Stein
Rotten Tomatoes Score: 65%
Rating: G
Runtime: 90 minutes

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Three franchises mostly define George Miller’s almost five-decade career: Mad Max, Happy Feet and Babe—the latter comprised by the two films Miller wrote about the talking pig who thinks he’s a sheepdog. Miller has kept such a distinct visual language throughout these 50-some years, we can draw a direct aesthetic line between Fury Road’s lavish colors depicting the grotesque beauty of a post-apocalyptic hellscape, and Babe: Pig in the City’s old-school fairy-tale world, equally enchanting and deadly. It’s is a textbook example of solid sequel-making: Instead of blindly recreating the charming family drama of Babe, following the titular pig hell-bent on defying his social place in his world, Miller dials the story’s fantasy to 11 to take us to an awe-inspiring metropolitan city that’s a hodgepodge of the most beautiful and recognizable urban spots in the world. Pushing human characters even more to the background, Miller’s film tells of Babe’s latest exploit leading a group of plucky and downtrodden animals in their quests for freedom and dignity. Like so many classic children’s entertainments, in Pig in the City, horrors lurk around every corner but the possibilities of life’s wonders similarly shine. —Oktay Ege Kozak



39. The Gold Rush

chaplin_gold_rush_poster.jpg Year: 1925
Director: Charlie Chaplin
Stars: Charlie Chaplin, Mack Swain, Tom Murray, Georgia Hale
Rotten Tomatoes Score: 100%
Rating: NR
Runtime: 82 minutes

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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).



40. Elf


elf_poster.jpg Year: 2003
Director: Jon Favreau
Stars: Will Ferrell, James Caan, Bob Newhart, Zooey Deschanel, Mary Steenburgen, Ed Asner
Rotten Tomatoes Score: 84%
Rating: PG
Runtime: 97 minutes

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In a sense, making Christmas “funny” can be as easy as responding to something meant to be sincere and joyful with cynicism and darkness. Is there any comedic Christmas character that embodies a genuine love of Christmas? Thankfully, we have Will Ferrell’s fearlessly committed performance as the titular elf to answer this question with a resounding yes. Nothing represents Christmas cheer better than Will Ferrell in yellow tights, a green parka and cone-shaped cap. He wrings a ton of comedy out of responding to everything with wide-eyed, childlike wonder. Arguably our generation’s classic Christmas movie, watching Buddy the Elf makes you laugh, makes you smile and, to paraphrase from the Grinch, makes your heart grow three sizes bigger. Even if the movie devolves into a formulaic, race-against-the-clock flick in the last 30 minutes, its myriad gifts outweigh its problems. From endlessly quotable nuggets like “cotton-headed ninnymuggins”; the hysterical fruit spray scene; Zooey Deschanel showcasing her pre-She & Him singing chops; Mr. Narhwal and the arctic puppets (a band name if I ever heard one); to, finally, Ferrell’s infectious enthusiasm, Elf is instant holiday merriment. —Greg Smith & Jeremy Medina



41. Clerks

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Year: 1994
Director: Kevin Smith
Stars: Brian O’Halloran, Jeff Anderson, Marilyn Ghigliotti, Lisa Spoonauer, Jason Mewes, Kevin Smith
Rotten Tomatoes Score: 89%
Rating: R
Runtime: 91 minutes

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Does Clerks hold up? That’s a tough question. It’s the exact same movie it was in 1994, obviously, as unapologetically raunchy and jaded as ever. It’s at once barely competent as filmmaking and yet probably the most artistically cohesive and competent work Kevin Smith has ever made. Clerks was never really a great movie, per se, but made a deep impression for two reasons. First off, the rags-to-riches story behind its creation was basically the ultimate summation of the entire 1990s fascination with indie films. Here’s a guy who made an ugly, lo-fi, black-and-white comedy without professional actors for less than a year’s worth of college, and because it had a voice and verisimilitude that hadn’t really hit the big screen yet, he got distribution through the biggest indie film company of the day and the movie wound up making millions. Secondly, if you were a teenager or twentysomething at the time, Clerks was legitimately hilarious. These characters spoke like your friends, or at least like amplified versions of them. It’s far from a great movie, and most of the acting is as terrible as you probably remember, but it still has that middle-class wastrel charm that made it stand out 24 years ago, and some of the jokes still land, even if your taste in comedy has changed greatly since you first saw it. —Garrett Martin



42. The Player

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Year: 1992
Director: Robert Altman
Stars: Tim Robbins, Greta Scaachi, Fred Ward, Whoopi Goldberg
Rotten Tomatoes Score: 98%
Rating: R
Runtime: 124 minutes

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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



43. Rush Hour

rush_hour_poster.jpg Year: 1998
Director: Brett Ratner
Stars: Jackie Chan, Chris Tucker, Tom Wilkinson, Elizabeth Peña, Philip Baker Hall
Rotten Tomatoes Score: 61%
Rating: PG-13
Runtime: 98 minutes

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The energetic tension in Rush Hour doesn’t just come from a difference in personality, but in cultural intensity, as well. Carter (Chris Tucker) is an African-American man from L.A. and Inspector Lee (Jackie Chan) is from the Hong Kong Police Force. The two team up to rescue a kidnapped girl. Most of the jokes play off of their race and ethnic backgrounds, but it’s never done in a distasteful way (at least in this first installment). The relationship between Carter and Lee is unpredictable, but always funny.—Michael Burgin



44. Austin Powers


austin-powers.jpg Year: 1997
Director: Jay Roach
Stars: Mike Myers, Elizabeth Hurley, Michael York, Seth Green, Robert Wagner, Carrie Fisher
Rotten Tomatoes Score: 70%
Rating: PG-13
Runtime: 90 minutes

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Austin Powers: International Man of Mystery was a cultural touchstone when it was first released thanks to Mike Myers’ instantly iconic performance and plethora of catchphrases, but it’s really a more clever film than it’s ever truly been given credit for (unlike its sequels). A loving spoof on the entire genre of spy movies, rewatching it now is especially rewarding, given the recent announcement that the upcoming James Bond film will be dealing with the classic villain organization “SPECTRE.” With the possible return of Bond villain Ernst Stavro Blofeld, audiences may finally understand that the character of Dr. Evil is an almost perfect parody of more serious Bond source material. Austin Powers may be a true ‘90s time capsule, but many of the jokes have improved with age.—Jim Vorel



45. The Ruling Class

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Year: 1972
Director: Peter Medak
Stars: Pete O’Toole
Rotten Tomatoes Score: 83%
Rating: PG
Runtime: 154 minutes

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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



46. Man Bites Dog

man-bites-dog-movie-poster.jpg Year: 1992
Directors: Rémy Belvaux, André Bonzel, Benoît Poelvoorde
Stars: Rémy Belvaux, Benoît Poelvoorde, Andre Bonzel
Rotten Tomatoes Score: 100%
Rating: NC-17
Runtime: 97 minutes

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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



47. Singin’ in the Rain

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Year: 1952
Directors: Stanley Donen, Gene Kelly
Stars: Gene Kelly, Debbie Reynolds, Donald O’Connor, Jean Hagen, Rita Moreno
Rotten Tomatoes Score: 100%
Rating: G
Runtime: 103 minutes

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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.—Garrett Martin



48. Swingers

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Year: 1996
Director: Doug Liman
Stars: Jon Favreau, Vince Vaughan, Ron Livingston, Patrick Van Horn, Alex Désert, Heather Graham
Rotten Tomatoes Score: 87%
Rating: R
Runtime: 96 minutes

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With their breakout roles in Swingers, Vince Vaughn and Jon Favreau established the personalities that still define them 20 years later. Vaughn’s a fast-talking Eddie Haskell type who isn’t quite as charming as he thinks, and Favreau’s an affable everyman with a sensitive side. This carries over to their recent work: Vaughn motormouths his way through comedies and dramas alike, while Favreau makes big budget Hollywood films that tend to be a little bit smarter and better crafted than most. The ease and charm of their friendship is what makes Swingers so memorable—it would’ve been called a bromance so often if that portmanteau existed in 1996. Swingers is a character-first comedy that captures a specific time and place in vivid detail. —Alan Byrd



49. Bevery Hills Cop

beverly-hills-cop.jpg Year: 1984
Directors: Martin Brest
Stars: Eddie Murphy, Judge Reinhold, John Ashton, Lisa Eilbacher, Ronny Cox, Steven Berkoff
Rotten Tomatoes Score: 83%
Rating: R
Runtime: 105 minutes

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We might remember Beverly Hills Cop for Eddie Murphy’s one-liners and that perfect microcosm of 1984, “Axel F,” but at its heart, it’s an action movie. In fact, Mickey Rourke and Sylvester Stallone were both attached to Murphy’s role before last-minute re-writes catered the story to the SNL actor. And this was Murphy at his cocky, wise-cracking best—always in complete charge of the situation no matter how much of a fish-out-of-water his Axel Foley might have been.—Josh Jackson



50. Josie and the Pussycasts

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Year: 2001
Directors: Harry Elfont, Deborah Kaplan
Stars: Rachael Leigh Cook, Rosario Dawson, Tara Reid, Parker Posey, Alan Cumming
Rotten Tomatoes Score: 53%
Rating: PG-13
Runtime: 99 minutes

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Josie and the Pussycats isn’t the disaster many thought it was when it came out, but it’s also not quite the brilliant, subversive satire that many today have tried to argue. It’s an occasionally funny, occasionally audacious parody of pop culture that criticizes the corporate vacuousness of the entertainment industry, but lightly, and only to the extent that that same industry would let a thoroughly corporate product like this criticize it. Is it better than most disposable turn-of-the-century teen comedies? Of course. Is it a fun way to kill 100 minutes? Yeah, especially if you’re old enough to be nostalgic for that era and get the movie’s pop cultural references. Is it some brilliant lost classic waiting to be rediscovered? Not quite. It’s a slick, silly film smart enough to update an old Archie comic into an irreverent, self-referential comedy, and that’s more than good enough.—Garrett Martin

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