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

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The 50 Best Comedies on HBO Max Right Now (September 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. Best in Show

best_in_show_poster.jpg Year: 2019
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


2. 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


3. A Shot in the Dark

movie poster shot in the dark.jpg Year: 1964
Director: Blake Edwards
Stars: Peter Sellers, Elke Sommer, George Sanders, Herbert Lom
Rating: PG
Runtime: 102 minutes

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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


4. 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


5. The 40-Year-Old Virgin

netflix 40 year old virgin.jpg
Year: 2005
Director: Judd Apatow
Stars: Steve Carell, Catherine Keener, Paul Rudd, Seth Rogen, Romany Malco, Kat Dennings, Elizabeth Banks, Leslie Mann
Rotten Tomatoes Score: 85%
Rating: R
Runtime: 112 minutes

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Judd Apatow emerged as a major new voice in the world of romantic comedy with his first directorial effort, The 40-Year-Old Virgin—a big, goofy, hilarious mess of a movie that is anchored by the easy charm of its two principal leads, Steve Carell and Catherine Keener. Their no-nonsense romance is surprisingly understated and adult in a movie with an outrageous premise and lewd jokes. Leslie Mann also deserves credit for that hilarious French toast scene.—Jeremy Medina


6. Clueless

clueless_netflix_poster.jpg
Year: 1995
Director: Amy Heckerling
Stars: Alicia Silverstone, Stacey Dash, Brittany Murphy, Paul Rudd, Dan Hedaya, Donald Faison, Breckin Meyer, Jeremy Sisto
Rotten Tomatoes Score: 81%
Rating: PG-13
Runtime: 97 minutes

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The Beverly Hills reboot of Jane Austen’s classic Emma was a sleeper-smash in 1995—and much more importantly, gave the phrase “As if!” to pop culture. Alicia Silverstone is Cher, a pretty, vain, superficial LA teen who goes on a mission to turn ugly-ducking classmate Tai (Brittany Murphy) into a Superswan, only to find herself eclipsed and adrift. A soft-edged satire of nouveau-riche Angeleno culture and simultaneously of the teen rom-com genre, Clueless is neither the most subtle nor the most hard-hitting film of its era, but it’s surprisingly seductive, in large part thanks to Amy Heckerling’s scrupulously researched script, which captured a dialogue style that both represented and influenced teen-speak of the time. —Amy Glynn


7. Friday

friday netflix poster.jpg
Year: 1995
Director: F. Gary Gary
Stars: Ice Cube, Chris Tucker, Nia Long, Tommy “Tiny” Lister, John Witherspoon, Anna Maria Horsford
Rotten Tomatoes Score: 78%
Rating: R
Runtime: 91 minutes

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In Straight Outta Compton we witness Ice Cube finish writing Friday with finality, as if he’d begun a week prior by declaring, “I will now write a screenplay,” and then a week later at his kitchen table putting down a pen and saying, “There. I’m finished.” We’re willing to accept that Ice Cube once did little more than decide to write a screenplay, and then did, and then made the movie, and then people loved it, because in that movie Ice Cube is our hero, a person who found no real difference, no barrier of entry, between wanting to do and then doing, despite much of his world forcefully telling him otherwise. In Friday, Ice Cube plays Craig, a young guy from south central L.A. whose best friend Smokey (Chris Tucker) implicates him in a $200 debt to Big Worm (Faizon Love), among the many problems Craig encounters throughout the course of the day. Chief among them: Deebo (Tony Lister Jr.), the neighborhood bully so without human empathy he’ll steal a man’s bike and then wait for the man to return just to uppercut him so hard the man’s lifted a few feet in the air. At least that’s how Smokey tells it. Craig even responds, laughing, “You’re lying,” but later Smokey’s story is proven true, at least in spirit, when Craig brains Deebo with a brick instead of shooting Deebo with a gun, which up until that point seemed to be the only viable option. The gun never fires, though it was introduced in the first act. Even if something like that matters to you, chances are that in Friday you never noticed. —Dom Sinacola


8. The Graduate


the grduate poster.jpg
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


9. The Wedding Singer

wedding_singeR_poster.jpg
Year: 1998
Director: Frank Coraci
Stars: Adam Sandler, Drew Barrymore, Christine Taylor, Allen Covert, Matthew Glave
Rotten Tomatoes Score: 69%
Rating: PG-13
Runtime: 96 minutes

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Over 20 years removed, Frank Coraci’s vision of the mid-’80s by way of the late-’90s bears the pastel aesthetic and pop culture refuse of a parody of that decade more than a clear memory of what was actually going on, but all the better to ground the then-popular caricature of Adam Sandler in a tender role best suited to his natural baby-man weirdness. What Happy Gilmore and Billy Madison did for Sandler’s “stop looking at me swan” voice, The Wedding Singer did for every other aspect of the comic actor, not only mitigating all that past frat boy dipshittery, but demonstrating that he could be a quiet, lovable leading man—a persona he’d go on to hone with his best films (notably, Punch-Drunk Love and The Meyerowitz Stories). The story of a banquet hall’s in-house crooner, Robbie Hart (Sandler), suffering a broken heart (like his name!) to find his way to the true girl of his dreams (Drew Barrymore, simultaneously endearing and cloying) hits each rom-com beat so squarely it’s nearly impossible to not see where this thing is going, but its heady brew of ultra-nostalgia and surreal poptimism, as well as Sandler’s unforced hilarity, serves the genre beautifully. The movie’s only glaring miscue is the repeated lambasting of Robbie’s bandmate George (Alexis Arquette), who navigates an onslaught of audience booing every time he sings Culture Club’s “Do You really Want to Hurt Me?” Since the movie takes place in 1985, the song’s been a certifiable hit for more than two years. The audience’s revulsion is more of a cheap gag than a cultural reality, a mis-remembered joke from a manufactured history—like much of the ’80s of The Wedding Singer, as dated today as it was in 1998. —Dom Sinacola


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. Pee-Wee’s Big Adventure

peeweebigadventureposter.jpg
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


12. When Harry Met Sally

when-harry.jpg
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


13. 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


14. The Birdcage

the_birdcage_poster.jpg Year: 1996
Director: Mike Nichols
Stars: Robin Williams, Gene Hackman, Nathan Lane
Rating: R
Runtime: 119 minutes

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You know what’s awkward? When you’re a middle-aged gay Jewish South Beach drag club owner (Armand, played by Robin Williams) and your straight son shows up and asks for your blessing to marry his girlfriend who is the daughter of a Neocon senator (Gene Hackman) who heads something called “The Coalition for Moral Order.” You want to support your kid, but you don’t love being closeted by him, and the dinner meet-up ends up meaning you and your partner, Albert (Nathan Lane), are forced into a whole new level of drag in which you are straight, a cultural attaché to Greece, and married to the one-night stand straight-sexperiment (Katherine, played by Christine Baranski) that led to the conception of your son. Your partner’s offended, the Senator’s being investigated by the tabloids, tensions are running high and your houseboy Agador (Hank Azaria) has agreed to transform into a Greek butler named “Spartacus,” but let’s face it, tensions are running high on all sides-and that’s before your baby-mama gets caught in traffic and Albert sees the opportunity for the drag role of a lifetime. Fully Shakespearean hijinks ensue. The 1996 Mike Nichols remake of Edouard Molinaro’s La Cage Aux Folles was not really blistering social commentary, but beneath its glib feel-good star-vehicle exterior there are some depths you could easily miss while you’re distracted by the batshit-crazy and heavily sequined antics of Williams and Lane. It’s actually not only rambunctious and witty but, as with many of Robin Williams’ film roles, The Birdcage has a serious streak where a genuine investigation of personal identity is underway, and hypocrisy, acceptance, snobbery, and most of all, everyone’s individual style of “drag” (and hey, we all have one, even if we don’t always express it by putting on fake lashes and singing Sondheim) gets taken out for a much-needed exam. —Amy Glynn


15. Broadcast News


broadcast-news.jpg
Year: 1987
Director: James Brooks
Stars: William Hurt, Albert Brooks, Holly Hunter, Robert Prosky, Joan Cusack
Rotten Tomatoes Score: 98%
Rating: R
Runtime: 132 minutes

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Broadcast News, against the backdrop of television news, lets play out that age-old cinematic gold mine: the love triangle. But rather than remain just a backdrop, the profession of journalism is the key to our three main characters’ identities: Jane (Holly Hunter) is an extremely driven producer, known for being cool under pressure and unwaveringly excellent at her job; Aaron (Albert Brooks as uber-mensch) is her steadfast partner at work, an intrepid reporter whose dynamism in the field remains overlooked; and then there’s Tom (William Hurt), the new pretty boy anchor way more clever than he seems. Aaron and Tom’s battle for career recognition, as well as Jane’s affection, mirrors the constant balance television journalists must strike between entertainment and hard news. And in typical Brooks fashion, there is no easy resolution to that balance. —Maura McAndrew


16. 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


17. 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


18. 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


19. Punch-Drunk Love

punch-drunk-love.jpg Year: 2002
Director: Paul Thomas Anderson
Stars: Adam Sandler, Emily Watson, Philip Seymour Hoffman, Luis Guzman
Rotten Tomatoes Score: 79%
Rating: R
Runtime: 95 minutes

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It may be hard to recall now that we’ve all rallied around his talent—allowing him to transcend the stigma of his Netflix deal while he still profits ludicrously off it—but there was once a time when the world doubted Adam Sandler. Long before the Safdies or even Noah Baumbach got their time getting tight with the Sandman, we have P.T. Anderson to thank for inspiring such hope. Compared to the scope of There Will Be Blood, or the melancholy of Boogie Nights, or the inexorable fascination at the heart of The Master, or the obsession and obfuscation of Phantom Thread, Punch-Drunk Love—a breath of fresh, Technicolor air after the weight of Magnolia—comes off like something of a lark for Anderson, setting the stage for the kind of incisive comic chops the director would later epitomize, and complicate, with Inherent Vice. A simple love story between a squirmy milquetoast (Sandler) on the verge and the woman (Emily Watson) who yanks him back to life, Punch-Drunk Love is as confounding as it is a delight, an expression of unmitigated, sputtering passion—sad and febrile and, most importantly, optimistic about what anyone is truly capable of doing. This might be as sincere as Anderson gets. —Dom Sinacola


20. Dirty Rotten Scoundrels

dirty-rotten-scoundrels.jpg Year: 1988
Director: Frank Oz
Stars: Michael Caine, Steve Martin, Glenne Headly
Rotten Tomatoes Score: 88%
Rating: PG
Runtime: 110 minutes

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The story of two rival con men working a wealthy heiress is a comedy classic for two reasons: Steve Martin and Michael Caine. Watching Martin’s American street hustler Freddy Benson try to learn from and outwit his reluctant mentor, Caine’s refined British Lawrence Jameson, while they both desperately attempt to win a bet of swindling $50,000 from their agreed mark (Glenne Headly as Janet Colgate), offers plenty of laughs, even if the plot is fairly conventional. With Benson reduced to playing the dimwit Ruprecht, Steve Martin is in his physical comedy prime. —Josh Jackson


21. A Mighty Wind


a_mighty_wind_poster.jpg Year: 2003
Director: Christopher Guest
Stars: Christopher Guest, Eugene Levy, Michael McKean, Catherine O’Hara
Genre: Comedy
Rotten Tomatoes Score: 92%
Rating: PG-13
Runtime: 91 minutes

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There’s a reason mockumentaries and musical subjects work so well together, evidenced by A Mighty Wind. Detailing the folk and bluegrass artists who worked with music producer Irving Steinbloom, the film follows Mitch & Mickey, The Folksmen and The New Main Street Singers as they reunite to put on a tribute concert following Steinbloom’s passing. Not only are the songs created for the film toe-tapping good fun, but seeing Guest, McKean and Shearer reunite as band mates after working together on This is Spinal Tap and watching Levy and O’Hara work their magic together once again made the film a classic as soon as it hit theaters. —Amanda Wicks



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

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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. 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


31. 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


32. 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


33. 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


34. 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.


35. Evil Dead 2

evil-dead-2-poster.jpg Year: 1987
Director: Sam Raimi
Stars: Bruce Campbell, Sarah Berry, Dan Hicks, Kassie Wesley, Richard Domeier
Rating: R
Runtime: 84 minutes

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On the surface, Evil Dead 2 is essentially a remake of the first 1981 Evil Dead: Sam Raimi going back to an idea he clearly enjoyed with a bigger budget and more experience to “get it right” by upping the ante of the original. But Raimi also offers up some tweaks that fundamentally alter the nature and tone of the first film, changing the recipe from “horror with occasional moments of black comedy” to a more even mix of both that still doesn’t skimp on scares or guts. Bruce Campbell as Ash goes from being almost a passive “final girl” character in the first film to a much more capable, wisecracking hero right from the get-go, and significantly more of the film features him in a tour-de-force solo performance, which helps make Evil Dead 2 one of the most tightly paced horror films ever. It wastes no time, going straight into its comic violence within the first 10 minutes and never letting up. It’s a film indicative of the changing attitude toward zombies—at this point in the late ’80s it’s becoming rare that zombies are ever treated as simply “scary.” More and more frequently, they’re instead incorporated into madcap comedies and action films à la Evil Dead, and this is a trend that continued through the ’90s. —Jim Vorel


36. Alice Doesn’t Live Here Anymore

alice-doesnt-live-here-anymore-movie-poster.jpg Year: 1974
Director: Martin Scorsese
Stars: Ellen Burstyn, Kris Krisofferson, Diane Ladd, Harvey Keitel
Rating: PG
Runtime: 112 minutes

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Ellen Burstyn divorced Neil Burstyn in 1972, two years before Martin Scorsese released his fifth feature, Alice Doesn’t Live Here Anymore; she used her experiences in marital separation to shape the movie’s protagonist, a recently widowed housewife who takes tragedy as an opportunity to start afresh. Once upon a time, Alice Hyatt (Burstyn) enjoyed a career as a singer. After marrying her callous husband, Donald (Billy “Green” Bush), she ditched her dream to raise their son, Tommy (Alfred Lutter). Her fate represents its own tragedy, creating an uneasy tension between her past and present circumstances. To the eye, the movie bumps off Donald to liberate Alice from patriarchy’s stultifying grasp, but Scorsese, whom Burstyn sought for the director’s chair after seeing his 1973 masterpiece Mean Streets, tacitly acknowledges that Alice would rather be done with Donald through any means other than a fatal car accident. She seizes her second chance with both hands, making for her childhood hometown of Monterey with Tommy in tow, road tripping across the American Southwest, Phoenix to Tucson. Each stop forces her to consider the question of whether, after so many years, she’s capable of maintaining independence. She’s dealt abuse by the slick, charming Ben (Harvey Keitel), a married man who woos her into a relationship, and ignominies by her temporary job waitressing at a diner. Scorsese’s filmmaking is lively, but determinedly revolves around Burstyn’s wonderful, multilayered performance without stifling it: His aesthetic’s grit gives the narrative an anchor while she breathes vibrant life into the frames. Ultimately, it’s Burstyn’s indomitable spirit that drives Alice Doesn’t Live Here Anymore, affording a portrait of what women’s lives can look like when autonomy and choice are givens. —Andy Crump


37. 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).


38. 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


39. 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


40. 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


41. 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


42. Observe and Report

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Year: 2009
Director: Jody Hill
Stars: Seth Rogen, Ray Liotta, Michael Peña, Anna Faris, Jesse Plemons, Colette Wolfe
Rotten Tomatoes Score: 51%
Rating: R
Runtime: 86 minutes

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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


43. 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


44. 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


45. 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


46. 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


47. 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


48. Drinking Buddies


drinking-buddies.jpg Year: 2013
Director: Joe Swanberg
Stars: Anna Kendrick, Olivia Wilde, Jake Johnson, Ron Livingston
Rotten Tomatoes Score: 83%
Rating: R
Runtime: 90 minutes

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If you feel compelled to go full indie and can’t stand love stories with tidy, happy endings, Drinking Buddies should be your pick. It’s an unconventional romance in that most of the characters never commit to the relationships or infidelities we expect them to. Instead, it’s about temptation, the lies we tell ourselves in a relationship and the boundaries between friendship and romantic feelings. A scion of—but not full-fledged entry into—the mumblecore genre, its largely improvised dialog lends an air of reality to the conversations, but those expecting typical genre conventions may find themselves perplexed when you don’t get anything resembling the “wedding bells” ending of the typical romantic comedy.—Jim Vorel


49. Dirty Work


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Year: 1998
Director: Bob Saget
Stars: Norm Macdonald, Artie Lange, Traylor Howard, Christopher McDonald, Jack Warden, Don Rickles, Chevy Chase, Chris Farley
Rotten Tomatoes Score: 17%
Rating: PG-13
Runtime: 81 minutes

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In 1998 hope was high that Dirty Work would be Norm Macdonald’s Billy Madison, a surprise hit (and surprisingly good) comedy that would propel him to Adam Sandler-level fame and success. Well, that didn’t happen. Dirty Work is still a greatly underrated film, one that fully integrates Macdonald’s distinctive comedic voice into a shaggy mainstream comedy full of clear ‘90s Hollywood signifiers. (Yes, “Semi-Charmed Life” is on the soundtrack. Yes, Christopher “Shooter McGavin” McDonald plays an uptight villain who, in a Hollywood comedy bingo twofer, is also an evil real estate developer who wants to evict Norm’s love interest’s grandmother. Yes, that love interest is played by a ‘90s sitcom actress, in this case Traylor Howard.) The film works because of Norm’s distinctive delivery and his character’s fractious relationships with his best friend and his best friend’s father, respectively played by Artie Lange and Jack Warden (in one of his final roles). Their chemistry, Norm’s charisma, and some sharp joke-writing elevates an otherwise predictable mediocrity.—Garrett Martin


50. We’re the Millers


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Year: 2013
Director: Rawson Marshall Thurber
Stars: Jennifer Aniston, Jason Sudeikis, Will Poulter, Emma Roberts, Ed Helms, Nick Offerman, Kathryn Hahn
Rotten Tomatoes Score: 49%
Rating: R
Runtime: 110 minutes

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For a while Hollywood would actually release R-rated comedies into theaters. Weird! We’re the Millers is a fairly standard example of the late ‘00s / early ‘10s, post-Hangover mainstream Hollywood comedy: it’s a little sour, and starts from a cynical place, but gradually turns saccharine as it tries to inject heart and warmth into its disfunction. The high concept: Jason Sudeikis is a small-time drug dealer who has to smuggle pot across the border to make good with his source, and to get past immigration he hires a stripper (Jennifer Aniston), a stray (Emma Roberts), and a random kid from his neighborhood (Will Poulter) to act like his family. Sudeikis and Aniston are fine, Nick Offerman and Kathryn Hahn reliably get laughs as an off-duty DEA agent and his wife, but Will Poulter pretty much steals the show as the one true innocent among the bunch who’s just happy to have something that feels like a family for once. The rough edges start very smooth and are quickly sanded down and polished up to a blinding degree, but We’re the Millers is more inoffensive and amiable than most of similar movies of its era.—Garrett Martin