The 100 Best Comedies of All Time

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50. Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006)
Director: Larry Charles

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It’s easy to overlook or underrate Borat in 2016, or Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan, given the Sacha Baron Cohen movies that followed. The likes of Bruno and The Dictator managed to water down Cohen’s original statement, but his faux-documentary about an awkward Eurasian traveler remains kind of brilliant. It was a wide-release comedy that plainly and critically looked at an average American attitude of dismissiveness and outright xenophobia toward people we don’t understand, as well as a willingness to feign earnestness if they thought taking advantage of Borat might somehow benefit them. Borat might say things that are naive, but at least they’re sincere products of the character’s fictitious upbringing. Borat the character is no charlatan—the “real” people he meets in America, on the other hand, can’t make the same claim. One final aside: This film, along with Anchorman, is the loudest I’ve ever heard an audience laugh in a multiplex theater. —Jim Vorel


49. Ghostbusters (1984)
Director: Ivan Reitman

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As the slew of ’80s merchandise and a cartoon series would prove, Ghostbusters had mass-appeal with kids. The film followed a team of parapsychologists—played by Dan Aykroyd, the late Harold Ramis, Ernie Hudson and Bill Murray—who tackle big-ghost issues in New York City. Sure some of the effects are dated, but this one has staying power. And although the bad guys come from beyond the grave, they’re also kid-friendly, with the begging-to-be-a-plush-toy Slimer and a giant Stay-Puft Marshmallow Man. Pass this classic comedy along to the next generation. —Tyler Kane


48. L.A. Story
Director: Mick Jackson

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Few would argue that Steve Martin doesn’t receive his due as a comedian. Nonetheless, among his filmography, L.A. Story does not always get the attention shown earlier efforts such as The Jerk or Planes, Trains and Automobiles or the somewhat blander fare that came in the 2000s. Depending on how one looks at it, that’s shame or perhaps just an opportunity to discover a hidden gem among Martin’s impressive oeuvre. In the hands of a lesser artist, L.A. Story could have easily just been another hit-or-miss collection of cultural clichés—sustained whimsy is not easy to pull off. Instead, Martin’s writing, Mick Jackson’s direction and a stellar cast present a beguiling love letter to the City of Angels and the people who live there. (If you’ve ever wondered how Sarah Jessica Parker became a star, consider this film Exhibit A.) Other Martin films on this list may well yield more laughter by volume, but L.A. Story will bring a smile on your face, and keep it there for the duration. —Michael Burgin


47. The Naked Gun (1988)
Director: David Zucker

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The final hoorah from the comedy trio David Zucker, Jim Abrahams and Jerry Zucker—ZAZ for short—The Naked Gun is so stupid it’s hilarious. This, of course, was ZAZ’s secret weapon in films like Airplane!, and in Leslie Nielsen’s stone-faced imbecility they found their muse. A former dramatic actor, Nielsen rejuvenated his career by playing Frank Drebin, a hapless L.A. police detective trying to prevent the assassination of Queen Elizabeth. (And in his courting of possible femme fatale Priscilla Presley, he taught us the importance of wearing full-body condoms.) A wonder of slapstick and deadpan silliness, The Naked Gun makes jokes about terrorists, gay panic, boobs, even “The Star-Spangled Banner.” There’s a character named Pahpshmir. Good lord, it’s all so gloriously idiotic. —Tim Grierson


46. Arsenic and Old Lace (1944)
Director: Frank Capra

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Some films are artistically groundbreaking and writ-large Important. Some are just such a good time that they last decade after decade. Frank Capra’s adaptation of this darkly comedic Broadway play (some of the Broadway cast reprised their roles in the film) stars Cary Grant as Mortimer Brewster, one of a family of Mayflower bluestocking WASP types who have, over the generations, become—I think the phrase is criminally insane? Brewster, an author of many tomes on the stupidity of marriage, gets married. On the eve of the honeymoon he drops by his family home to meet check in with his loony and sweetly homicidal aunties, a charmingly delusional uncle who believes he is Theodore Roosevelt, and his brother, Jonathan, who has bodies to bury and a flat-out crazy alcoholic plastic surgeon in tow. Peter Lorre plays the surgeon, who has altered Jonathan’s face to make him look like Boris Karloff (naturally). And that’s just the setup. More than seven decades after its release, this film is still snort-soda-out-your-nose funny. Even though it’s tame, and a bit hammy by contemporary standards, the endurance of this film is a testament to both the wonderful script and the magic of Frank Capra with a stable of really talented comedic actors at his disposal (and not in the “bodies in the basement” sense). —Amy Glynn


45. Being There (1979)
Director: Hal Ashby

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In terms of directorial output in a decade, Hal Ashby’s run in the 1970s is impressive. Starting with 1970’s The Landlord and ending with Being There, Ashby’s films racked up 24 Oscar nominations and seven wins. But while Harold and Maude, Shampoo and Coming Home compete for the hearts and minds of Ashby fans, it’s Being There that stands out both for its timelessness and timeliness. In the story of the childlike Chance (Peter Sellers, in a role that redeemed a sagging reputation), a gardener whose innocence and simplicity confuses and gets misread by the “savvy” players of Washington, D.C., Ashby shows how gentle humor can express sharp truths about all-too-human foibles. —Michael Burgin


44. There’s Something About Mary (1998)
Directors: Bobby Farrelly, Peter Farrelly

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This was the moment Ben Stiller became Ben Stiller and Cameron Diaz became everyone’s crush. There’s Something About Mary was a movie that loved its protagonist but let us all laugh with him as every wrong decision (and unfortunate zip) compounded with serious interest. We love this movie the way Ted (plus characters played by Matt Dillon, Chris Elliott and Brett Fav-er-uh) love Mary—a little obsessively.—Josh Jackson


43. Office Space (1999)
Director: Mike Judge

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Great comedy almost always has a dark heart. (The flipside is also true of great horror: it almost always teeters on the edge of farce). But this makes sense. Laughter is our response to absurd and unexpected contradictions; comedy needs its darkness to fully flourish. Mike Judge, the writer/director of Office Space, knows this well. His humor concerns the lowest, saddest schmucks on the corporate ladder (thus 99% of us can relate) who mostly feel dead inside, turning to Kung Fu reruns and cheap beer to escape. It’s a subject as old as capitalism itself: most of us are unhappy, not doing what we want, feeling our dreams escaping us more and more with each passing day. For protagonist Peter Gibbons (Ron Livingston), his goal is one of the funniest and most subversive in cinema history: independently, from no wellspring of societal angst (unlike, say, The Graduate’s Benjamin Braddock), he wants to do nothing. And besides being a hilarious antidote to scores of boring predictable cookie-cutter hyperactive hero-protagonists that populate seemingly every movie (the Office Space pitch meeting: “the hero’s goal is nothing!”), it feels absolutely real, and is what the corporate rat race deserves in an anti-hero: the do-gooder replaced by the do-nothing. It also helps that Judge has a perfect cast. Together, they turn caricature into depth, a cartoon (the source material) into vivid life. More importantly, they also make a very funny movie. —Harold Brodie


42. Four Lions (2010)
Director: Chris Morris

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Four Lions proves once again that great comedy can be extracted from the dodgiest and most painful subjects, mixing slapstick with dry British humor to tell the story of four would-be radical Islamic terrorists hell-bent on bringing down the evil capitalist heathen of the West. Only one problem (well, a couple of them): They have no real connections, skills, or ability to plan anything, suffering from varying degrees of resolve when it comes to blowing themselves up for their cause. In other words, they are terrible at their dream jobs. As unrelenting as Four Lions can be in the way that it pokes fun of its central four characters, they film never adopts a farcical tone, instead never shying from the dangerous ramifications of their actions, no matter how incompetently they go about them. Deftly executed by co-writer/director Christopher Morris, who should be known States-side as the neurotic boss during the first season of The IT Crowd, and a pre-mopey, pre-The Night Of Riz Ahmed in a hilarious leading turn, Four Lions demonstrates a careful, masterful directorial hand. Plus it contains the best line about suicide bombing in any movie: “His soul will reach heaven before his head hits the ceiling.” —Oktay Ege Kozak


41. Ferris Bueller’s Day Off (1986)
Director: John Hughes

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John Hughes’ zeitgeist-y, fourth wall-busting ode to rich, entitled suburban youth vs. killjoy authority announced Matthew Broderick as a bona fide star, and gave us a chillingly prescient glimpse at Charlie Sheen’s future in an admittedly funny bit role. Breakfast Club aside, out of all Hughes’ decade of teen-centric movies set in the Chicago area, Bueller has almost certainly endured the best, and without all that tortured pretentiousness. —Scott Wold


40. Safety Last! (1923)
Directors: Fred C. Newmeyer, Sam Taylor

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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 famous 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 to it. —Jeremy Mathews


39. Friday (1995)
Director: F. Gary Gary

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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


38. Rushmore (1998)
Director:   Wes Anderson  

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Rushmore introduced the world to Jason Schwartzman and helped pivot Bill Murray’s career from broad comic to art-house juggernaut. An unlikely inter-generational love triangle leads to one of the most entertaining feuds in filmdom. Schwartzman’s Max Fischer is an ambitious yet academically underachieving student at the prestigious Rushmore Academy in Houston, and Bill Murray plays wealthy industrialist Herman Blume. The two strike up an unexpected and unconventional friendship, but both end up falling for Rosemary Cross (Olivia Williams), a teacher at Rushmore. When Max goes too far in trying to prove himself to Ms. Cross by breaking ground on a new building without the school’s permission, he’s finally expelled and ends up in a soul-crushing public school. To make matters worse, he finds out that Herman has begun dating the object of his desire. As with Bottle Rocket, Rushmore was co-written by Owen Wilson who, like Max, was expelled from a prep school. He and Anderson began work on the script long before Bottle Rocket was filmed, and Rushmore contains even more of the DNA found in the rest of Anderson’s catalog. Few films remain re-watchable into the double digits, but this one just keeps getting funnier. —Josh Jackson


37. Singin’ in the Rain (1952)
Directors: Gene Kelly, Stanley Donen

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Though only modestly successful upon release, Singin’ in the Rain rose in critical esteem to become widely considered the best movie musical of all time. A comedic take on the difficult 1920s transition from silent film to “talkies,” the film stars Gene Kelly as a popular silent film star (and dancer, of course), and Jean Hagen as the vain and irritating costar his studio keeps pairing him with romantically. Perhaps the definitive MGM Technicolor musical, the story is adorable and the singing is terrific, but I’m not sure any of its many, many virtues can top the pure explosive vitality and joy that is Gene Kelly in motion. I defy you to watch this and not feel ridiculously happy. —Amy Glynn


36. Wet Hot American Summer (2001)
Director: David Wain

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A cult film that’s long since surpassed that status, Wet Hot American Summer is a lot of things: It’s hilarious; it’s perfectly cast; and it’s a clear demonstration that Christopher Meloni has more range than simply playing a dour sex crime detective. But what makes it so brilliant, 15 years later and with a Netflix series on lock, is that it’s so painfully, relentlessly nihilistic. We could trade quotable lines for days (my personal favorites being what Jon Benjamin’s can of vegetables admits he’s acrobatically capable of, and then Paul Rudd bluntly refusing to make out with Elizabeth Banks’s character due to her burger flavor), but the key to the movie’s endurance—past its timelessness grounded in a specific brand of ’80s sex romp flick—is the way in which it treats nostalgia. Like Wain, Michael Showalter and Michael Ian Black’s Stella series, Wet Hot American Summer, which takes place over the course of Camp Firewood’s last day, exists in a bleakly amoral world. Here, bad things happen to good people—and really only to good people. Wain takes innocence and obliterates it, punishes it, gleefully destroying all nice memories anyone would ever hold dear about long lost summers, first loves and youth. Without a shred of wistfulness, Wet Hot American Summer surpasses its origins in parody and becomes something more: It earns its comedy. Taunting our very explicitly American tendency to let everything we touch devolve into sentimentality, the film proves that when we obsess over remembering ourselves at our best, we might as well be celebrating us at our worst. —Dom Sinacola


35. Horse Feathers (1932)
Director: Norman Z. McLeod

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Before Animal House and Old School even thought of poking fun at American college life, there was the hysterical Horse Feathers, the 1932 film that shows Groucho as newly appointed Professor Quincy Adams Wagstaff. We see Wagstaff attempt to recruit true pros for the university football team, which results in newly enrolled Harpo and Chico wreaking havoc across the university. —Tyler Kane


34. Caddyshack (1980)
Director: Harold Ramis

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There are four faces on the Caddyshack poster, and all of them are equally crucial to the film’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


33. The Kid (1921)
Director: Charlie Chaplin

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Leave cynicism at the door: The Kid is for the wide-eyed optimists of the world. This loving movie is often hilarious and at times truly heart wrenching in its portrayal of a father and his adopted son. With the restored 4K version of Chaplin’s 1972 rerelease, he has never looked better on Blu-ray. Jackie Coogan also shines, running the gamut from giggles to tears in the role of John, and Chaplin’s Tramp character may not have been portrayed more sweetly than here. His full-length feature debut, The Kid is the work of a true auteur, and a serious master. In the realm of comedy Chaplin manages a wealth of emotions, something that would follow with his later, more politically charged films. The power and depth of 1952’s Limelight can still be traced back to The Kid. Chaplin knew what he was doing, and there’s nothing juvenile about this early work. Special features include audio commentary by Chaplin historian Charles Maland, as well as deleted scenes and titles from the original 1921 version. Do not ignore this one, cinephiles. —Nelson Maddaloni


32. Sullivan’s Travels (1941)
Director: Preston Sturges

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How much does an artist need to suffer for their art? Can a storyteller tell a story that isn’t their own? When are you making an honest-to-goodness piece of art, and when are you just playing a sick game of nostalgie de la boue? Sullivan’s Travels doesn’t exactly answer these questions as much as it wields them like blunt instruments for punishing its protagonist, John L. Sullivan (Joel McCrea), a hot ticket in Hollywood known for churning out money-making flicks with no substantive value. He’s a fraud, his work is empty, and he knows it, so like any hack who desperately needs artistic validation to assuage his feelings of creative guilt, he hefts a hobo stick over his shoulder and hits road in the guise of a down-on-his-luck tramp, followed all the while by a lavish double-decker bus as well as the inescapable grip of his own prestige. If you’re a fan of the screwball niche of comedy filmmaking, you have to know Sullivan’s Travels, one of the best examples of its category; screwball movies aren’t simply about zaniness but energy, inertia, momentum, the snowballing power of a silly premise when backed by an intelligently designed madness. —Andy Crump


31. Bull Durham (1988)
Director: Ron Shelton

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I believe in ridiculous names like Crash Davis and Nuke LaLoosh. I believe in romantic comedies about giving up on a certain phase of your life where characters stand up and deliver cliched “I believe” speeches that, despite being borderline cheesy, somehow ring completely true. And yes, I too believe there should be a Constitutional Amendment banning Astroturf and the designated hitter. I believe in Bull Durham. The most engaging presentation of the minor-league life on film—and a pretty salute to baseball, in general—this first installment in the unofficial Kevin Costner Baseball Trilogy proved that baseball could equal big box office. Costner and Susan Sarandon anchor this film that does its part to engender a love for the game and the people who court it. —Bonnie Stiernberg & Michael Burgin


30. The Odd Couple (1968)
Director: Gene Saks

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Few onscreen pairings in the history of cinema have boasted quite the same spark as Walter Matthau and Jack Lemmon, with the former’s bone-dry demeanor perfectly augmenting the latter’s flighty, neurotic energy. Out of the 11 (yes, 11) films the two did together, perhaps the quintessential entry for many is this 1968 adaptation of Neil Simon’s hit Broadway play, The Odd Couple. Here, Matthau plays slovenly sports writer Oscar, whose life is turned topsy-turvy when his cleanly, high-maintenance friend Felix moves in with him. In the decades since the film’s release, its high-concept premise has spawned so many imitations in both film and TV that the “odd couple” concept has become a sub-category of its own. However, despite all the numerous iterations of the story over the years, including a 1970s ABC comedy series, a well-received Broadway revival with Nathan Lane and Matthew Broderick and a forthcoming CBS series starring Matthew Perry and Thomas Lennon, few can hold a candle to what Matthau and Lemmon achieved with this first go-round. —Mark Rozeman


29. Anchorman: The Legend of Ron Burgundy (2004)
Director:   Adam McKay  

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Will Ferrell  was a movie star before 2004, carrying both Old School and Elf, but he is still inseparable from his role as San Diego newscaster Ron Burgundy, a character so closely tied to our perception of Ferrell as an actor that every subsequent role seems to contain shades of him. Now that McKay has an Oscar under his belt, he’s getting more recognition than he did when he was simply the man behind the camera on Ferrell’s best movies. Anchorman upped the ante on Zoolander’s sheer lunacy, and ended up being a better movie for it, but true to McKay’s Chicago improv routes, it is a plane forming itself mid-flight, and Anchorman would be two seconds from falling apart without McKay’s steady hand. Ferrell is a certifiable genius in his own right, and is undoubtedly the center of the universe in each of these films, but the world around Ferrell belongs to McKay, and Anchorman announced his arrival as an uncompromising comedy world-builder. —Graham Techler


28. The Big Lebowski (1998)
Director: Joel Coen

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Jeff “The Dude” Lebowski has plenty of time on his hands—enough to while away the days chasing down a stolen rug, at least—but he can hardly get himself dressed in the morning, chugs White Russians like it’s his job (incidentally, he doesn’t have a real one) and hangs around with a bunch of emotionally unstable bowling enthusiasts. Any mission you set him off on seems bound to fail. And yet that’s the great joy, and the great triumph, of the Coen BrothersThe Big Lebowski and its consummate slacker-hero. The Dude is a knight in rumpled PJ pants, a bathrobe his chainmail, a Ford Torino his white horse. Strikes and gutters, ups and downs, he takes life in ambling, unshaven stride—and more than dashing good looks and unparalleled strengths, isn’t that something we should all aspire to?


27. National Lampoon’s Vacation (1983)
Director: Harold Ramis

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After three sequels and a crappy—at times literally—“legacyquel,” the original Vacation is still the king of no-Fs-given raunchy family comedies. The main reason why the first film stands head and shoulders above the others (including Christmas Vacation) is very simple: It doesn’t treat the Griswolds as a bunch of innocent, puppy-dog-eyed stand-ins for some pure ideal of a white, American, middle-class nuclear family, one where a series of misfortunes happen through no fault of their own. In Vacation, the Griswolds are stunningly out-of-touch with their rapidly changing country: They’re vain, entitled and far too narcissistic to operate as a healthy family unit, to the point where we understand that even without the many unlucky situations they come across, their trip to Wallyworld would have still been a disaster. Through patriarch Clark Griswold, writer John Hughes, actor Chevy Chase and director Harold Ramis create the absolute icon of white baby boomer entitlement. Like many of his kind, Clark thinks he’s owed the world, everything he says or does is right and he has complete dominion over his family. When he doesn’t get the respect and adulation he knows he deserves, he doubles down on his stupidity and makes everything worse. That’s why the humor in Vacation is so much more palpable than the sequels; the comedy comes from the characters and deep-seated satire, not just outside circumstance and sitcom gags. Otherwise, Clark’s inevitable nervous breakdown scene would have come across as forced, instead one of the film’s funniest sequences. —Oktay Ege Kozak


26. Love and Death (1975)
Director:   Woody Allen  

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The very best of Woody Allen’s funnier, earlier films, Love and Death showcases Allen’s two favorite themes (see title). The absurdist plot centers on a young couple (Allen and Diane Keaton) who plot to assassinate Napoleon in czarist Russia. Garbed in one ridiculous costume after another, Allen’s character philosophizes on God, love, death and the meaning of life, in between zany antics and hilarious physical comedy. The balance between big ideas and featherweight comedy is seamless, making Love and Death the perfect segue into the more ambitious and complex films that followed. —Jeremy Medina

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