Keegan Michael-Key and Jordan Peele have a new movie, Keanu, in which they co-star with the world’s most adorable cat. And sure, the film has violent murders, epic shoot-outs, and George Michael sing-alongs but the real allure here is that cat. You know it. We know it. And Key and Peele know it.
So when we brought a little Keanu cat into our interview with Key and Peele, it only makes sense that the little fella stole that show as well. After the frisky critter crawls all over our host, William Bibbiani, Keegan-Michael Key takes point and whisks the kitten away, where it promptly falls asleep in his arms.
Also: An Actually Serious Interview with Key and Peele About ‘Keanu’
Sure, we were going to talk about Keanu, but the kitty cat hijacked the conversation completely, so instead here’s Key and Peele and William Bibbiani, kitten around and talking about cat stuff.
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William Bibbiani (everyone calls him ‘Bibbs’) is Crave’s film content editor and critic. You can hear him every week on The B-Movies Podcast and Canceled Too Soon, and watch him on the weekly YouTube series Most Craved, Rapid Reviews and What the Flick. Follow his rantings on Twitter at @WilliamBibbiani.
The Top 50 Funniest Comedies of All Time:
The 50 Funniest Comedies of All Time
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50. 22 Jump Street (2014)
In the modern era, the broad slapstick farce seems to have fallen by the wayside (largely thanks to a long string of super unfunny spoofs by hated duo Friedberg and Seltzer). Luckily, we have Peter Lord and Chris Miller to pick up the slack with their uncanny ability to take movies that sound like horrible ideas on paper (Legos? A 21 Jump Street movie?) and turn them into knowing and awesomely hilarious comedies. 22 Jump Street, a sequel to an unexpectedly funny original, turns the silliness up to 11, mining the banality of the Hollywood machine for a barrage of knowing, fourth-wall-breaking gags.
Funniest Moment: Over the credits, we get previews for the next 20 Jump Street movies.
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49. The Blues Brothers (1980)
The first “Saturday Night Live” movie, and easily the best, is based on a barely-there joke: white guys Dan Aykroyd and John Belushi, acting like serious blues musicians. But Aykroyd and director John Landis had more ambitious plans for the movie: a zippy musical, packed with great performances from all-star cameos and the most incredible and destructive car chases ever filmed. The Blues Brothers has more pizzazz than most other comedies combined, and with wall-to-wall silliness punctuating the dazzling set pieces, it’s also one of the funniest things ever committed to celluloid.
Funniest Moment: "They broke my watch!"
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48. The Cameraman (1928)
The 1928 silent comedy from Buster Keaton was his most self-referential, about a man whose career as a cameraman causes trouble on the road to a happy romance with a young woman (Marceline Day). It was Keaton’s first film for MGM, a studio that interfered with the creative control of the perfectionistic filmmaker, and the pairing sent him on a career downslide, but not before delivering this classic.
Funniest Moment: Keaton has to share a tiny dressing room with a big, burly man, and the outfit-changing war that follows is one of physical comedy’s greatest battles.
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47. UHF (1989)
It cannot be denied that comedy musician "Weird Al" Yankovic is one of the most formidable comedians of his, or any following generation. In the late 1980s, at a particularly high crest of his popularity, Yankovic decided to make a slapstick farce about a UHF TV station that succeeds on the strength of original shows like "Wheel of Fish," "Fun with Dirt," and educational shows that teach poodles how to fly. UHF was informed rather directly by the awesome slapstick of ZAZ (Airplane!, Top Secret!), and nearly brushed up against that greatness. UHF bombed in 1989, but has rightfully built a cult following since.
Funniest Moment: The preview for Gandhi II. "No more Mr. Passive-Resistance. He's out to kick some butt!"
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46. The Lady Eve (1941)
Barbara Stanwyck is a con artist out to romance-hustle rich guy Henry Fonda in Preston Sturges’ brilliant farce. That they fall in love anyway is part of its light-hearted charm, but don’t think you’ve got it all figured out – it’s full of twists and turns and smart dialogue, and it may be the finest of all the screwball comedies.
Funniest Moment: Stanwyck’s insistence on literally tripping Fonda as often as she can is only upstaged by gruff-voiced character actor Eugene Pallet’s relentless order barking as Fonda’s father.
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45. To Be Or Not To Be (1942)
Ernst Lubitsch's film was lambasted for political incorrectness because it was released during WWII. There are plenty of "Heil, Hitlers!" tossed about in this Jack Benny comedy—about actors becoming spies as the war hits Poland—but just like Shakespeare's writing there's double meaning with each repeated phrase: here "Heil, Hitler" is the simplest way to cover up someone's mistake by passing the blame upward. And with the Nazis there were many atrocities, and they all mounted unmitigated up to Hitler himself.
Funniest Moment: The opening scene. An actor (who's playing Hitler in a stage production), going out into the street to prove that he does indeed resemble mein fuhrer and therefore that his witty additions to the play should also be included.
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44. Bringing Up Baby (1938)
Cary Grant and Katherine Hepburn had chemistry, damn it, and their second outing together (after George Cukor’s amusing Holiday) sets off a chain reaction of laughs that don’t stop until “The End.” Grant plays a mild-mannered paleontologist who accidentally catches the eye of a rambunctious goof (Hepburn), who schemes to keep him by her side with the help of a newly acquired pet leopard. Bringing Up Baby is a masterpiece of comedic suffering, as Grant desperately tries to escape Hepburn’s clutches and keep innocent bystanders from getting eaten alive.
Funniest Moment: Cary Grant, frantically explaining why he's all of a sudden wearing a woman's bathrobe.
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43. Being John Malkovich (1999)
Being John Malkovich is damn near indescribable, because the plot summary of a puppeteer (John Cusack) selling tickets to enter a muddy passage behind a file cabinet that takes you into an acclaimed actor's brain for 15 minutes before being spit out on the New Jersey Turnpike just makes you ask “how?” Malkovich kinda answers that (because it has to) but only after screenwriter Charlie Kaufman has avoided it for damn near the entire length of this inventive and darkly humorous comedy about how much effort we put into trying to be someone else.
Funniest Moment: Malkovich enters the Malkovich portal (while another man is inside) and the only words the actor wants to hear (or read) is his own name.
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42. Monkey Business (1931)
Loosely story-free and freewheeling, Monkey Business is the best of the early Marx Bros. films (i.e. the ones to feature all four of them). The Marx Bros. were like jazz musicians, only instead of instruments, they had comedy, and instead of riffing on music, they riffed on every social trope of sane society. Monkey Business takes place on a ship at sea, and the brothers have stowed away. They flirt, play, tell jokes, and make a mockery of just about everything that wanders into their field of vision. And it's magical.
Funniest Moment: Harpo orders a hard-boiled egg.
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41. Step Brothers (2008)
Comedy’s trend of sympathetic man-children got the shredding it deserved when this film gave the world not one, but two extremely damaged and insecure narcissists in Will Ferrell and John C. Reilly. The two despicable boors manage to ruin the engagement of Reilly’s father to Ferrell’s mother, before having to team up to reunite the aging baby boomers in love. The punchline, of course, is that the dumb duo never really learn to be anything more than idiots. The end.
Funniest Moment: “You know what’s good for shoulder pain? If you lick my butthole.”
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40. Waiting for Guffman (1996)
Although Christopher Guest had worked in the semi-improvised mockumentary form before with This is Spinal Tap, I feel like he came into his own with Waiting for Guffman, a prim parody of small-world theater, and the bizarre amount of ego and undeniably sincere pride that can go into a production, no matter how small. The characters - all lovably blockheaded hayseeds - are broad, yet somehow believably clueless kids. They have some real talent too. Anyone who has been involved in theater can recognize these characters.
Funniest Moment: When Corky (Guest) loses his patience, and calls someone an "ass face."
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39. South Park: Bigger, Longer and Uncut (1999)
Nobody expected this was coming from the creators of the animated sitcom, but that was part of its magnificence. A brutal evisceration of uptight morality and the desire to censor, it also managed to mock musicals while sticking the landing of every song exploding out of the profane mouths of its cartoon-child cast, making it one of the best screen musicals of the era. So fuck yeah.
Funniest Moment: “You’re the one who fucked your uncle, Unclefucker.”
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38. Election (1999)
The best film satire of American politics comes from a high school presidential election: where a teacher (Matthew Broderick) tries to set a good example for his students, but ends up giving into sour grapes when the school's over-eager follower of the public school guide to success (joining every club so you look well-rounded for college applications), Tracy Flick (Reese Witherspoon), will go unchallenged due to student body apathy and acceptance of her as their pre-ordained leader.
Funniest Moment: Paul Metzler (Chris Klein)—whom Broderick is trying to sell on running for student body president—after deciding to run for president: "I sure was surprised the day Lisa Flanagan asked me for a ride home and ended up blowing me."
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37. The General (1926)
Buster Keaton’s most incredible accomplishment is this Civil War epic, equally blockbuster action thriller and broad comedy. Keaton plays Johnnie Gray, a train conductor who wants to enlist for the army but can’t, because he’s too valuable where he is. But his girlfriend Annabelle doesn’t know that and she brands him a coward. When both his engine and his lady are kidnapped by the enemy, Keaton sets out on a breathtaking chase, loaded with complex gags and overwhelming spectacle. Not just one of the best comedies, The General is one of the best movies of any kind.
Funniest Moment: Johnnie has finally rescued Annabelle, but she's more trouble than she's worth, forcing our hero to finally throttle her in frustration. (He apologizes.)
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36. Women on the Verge of a Nervous Breakdown (1988)
Actress Pepa (Carmen Maura) knows her lover Iván plans to leave her. Pepa’s friend Candela is in trouble for falling in love with a terrorist. Iván’s ex Lucía has snapped and thinks it’s still the early 1970s, when she and Iván were still together. Iván’s son’s girlfriend Marisa is uptight and frigid. These women need some slack, or at least maybe some gazpacho spiked with sleeping pills, in Pedro Almodóvar’s breakthrough farce.
Funniest Moment: Pepa and Candela chase a gun-toting Lucía through Madrid traffic on the way to the airport.
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35. Bedazzled (1967)
The Faust tale gets a Brit wit "generation me" makeover when a fry cook at Wimpy Burger (Dudley Moore) decides to sell his soul to the devil (Peter Cook) to get the server of his dreams. Because this is the height of mod, Stanley Donen's film gives us lots of great pop culture jokes about rock 'n roll, seduction, and goddamnit if the devil doesn't seem so happy: because finally, sin is in! Peter Cook's beelzebub is someone you might not wanna sell your soul to, but you really wanna meet him at the pub.
Funniest Moment: Signing the contract: "I, Stanley Moon, hereinafter and in the hereafter to be known as 'The Damned'—the damned?!"
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34. The Party (1968)
After accidentally ruining the remake of Gunga Din, Indian actor Hrundi V. Bakshi (Peter Sellers) is mistakenly invited to a swinging bash thrown by the film’s producer. If you can put aside the brownface being perpetrated by Sellers, this is one of his greatest comic creations, in a Blake Edwards farce that has the precision of Jacques Tati. Bakshi creates chaos wherever he goes, and by the end of the evening, this party will hilariously turn into a total disaster.
Funniest Moment: A toilet that won’t stop flowing and a roll of toilet paper that won’t stop unrolling.
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33. In the Loop (2009)
One of the best film satires of global politics comes from the man who would later give us Veep: Armando Iannucci. His In the Loop shows how two allied nations—Britain and the United States—are all in a rush to vote on a war. No one knows why they're involved, but they all want the record to show that they were there when the world needed them. Things escalate frighteningly quick, and with spot on ego portraits and documentary style. It’s all so scary because it doesn't feel like a stretch that elected officials would actually react similarly.
Funniest Moment: While Peter Capaldi's foul-mouthed UK communications chief got most of the laurels, for me, it's James Gandolfini (playing a Pentagon general) and Mimi Kennedy (Assistant Secretary of Diplomacy) who get the most laughs—and their scene together, calculating the possible death toll on a child's counting device is fantastic satire of childish war games.
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32. Dirty Rotten Scoundrels (1988)
For my money, this is Steve Martin's finest comedic performance. Martin plays a low-rent con man who asks a more experienced con man (played by Michael Caine) to teach him tricks of the trade. Their cons allow Martin to play various bizarre characters. As the title implies, the leads are unforgivably wicked, never once revealing a single scruple, and there's something refreshing about that. It's like a slapstick version of Mamet, but with poop jokes instead of banter.
Funniest Moment: Steve Martin plays Ruprecht the Monkey Boy to scare off wealthy dowagers.
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31. Raising Arizona (1987)
The Coen Bros. redefined the screwball comedy with this eclectic kidnapping farce, in which Nicolas Cage and Holly Hunter, unable to have children of their own, decide to kidnap a quintuplet from a rich millionaire who, they suppose, already has more than he can handle. Naturally it all spirals out of control, as Cage’s old bank-robbing buddies catch wind of the scheme and a seemingly supernatural bounty hunter puts them in the crosshairs. With a daring Huggies robbery and a climactic Road Warrior brawl, Raising Arizona bristles with manic, hilarious, quirky energy.
Funniest Moment: Gale and Evelle realize that they left Nathan Jr. at the bank they just robbed, and scream non-stop like banshees until they get him back.
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30. A Fish Called Wanda (1988)
Barrister Archie Leach (John Cleese) is falling hard for American Wanda Gershwitz (Jamie Lee Curtis), not aware that she’s playing him in order to get information about one of his clients, a thief to whom she’s an accomplice. Throw in Kevin Kline as a maniacal idiot who’s not nearly as smart as he thinks he is, and Michael Palin as a stutterer with a love of animals, and you’ve got one of the great fast-paced farces of the 1980s.
Funniest Moment: Kline’s Otto tries lying to Leach’s wife Wendy (Maria Aitken), only to dig himself deeper and deeper in a hole when it becomes clear that she, like most people, is much smarter than he is.
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29. The Jerk (1979)
“I was born a poor black child,” Steve Martin tells us, starting The Jerk off with some delicious absurdity. And off it goes from there, taking poor boob Navin R. Johnson from one ludicrous scenario to another, saying the dumbest stuff you’ve ever heard so sweetly that you love him anyway. The Jerk is one of Martin’s least elegant films, lacking the insight and rapier wit of L.A. Story or Roxanne, but it’s also the balls out silliest.
Funniest Moment: "He hates these cans! Stay away from the cans!"
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28. Tootsie (1982)
Perfectionist actor Michael Dorsey (Dustin Hoffman) can’t get hired — until he goes in drag as Steel Magnolia Dorothy Michaels and becomes the hit of daytime TV as a soap actress. Michael insists he’s just doing this to raise the money to produce the play written by his roommate (Bill Murray, deadpan and brilliant), but he falls in love with costar Julie (Jessica Lange). What will happen when Julie, and America, discover that Dorothy is really a dude?
Funniest Moment: Michael’s argument with his agent (director Sydney Pollack) in which he defends his choice not to sit down when playing a tomato in a TV commercial before bragging about the night of vegetables he played off-Broadway.
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27. Wet Hot American Summer (2001)
Not so much a movie as a rich tapestry of summer nostalgia and goofy gags, David Wain's Wet Hot American Summer parodies the beloved summer camp genre but carves a unique place out for itself as a sprawling ensemble piece. It’s like Robert Altman if Robert Altman were really, really dumb. A bunch of 30-somethings play teenaged camp counselors who kill their campers, deflect a doomsday satellite and learn the power of self-actualization from a can of peas, just like we all did, once upon a time.
Funniest Moment: The kids of Camp Firewood veto their big game against an "ambiguously evil" rival, arguing that the whole scenario is just kinda trite.
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26. Rushmore (1998)
Wes Anderson’s second feature ushered in the visual formality his comedy would take after Bottle Rocket. And Jason Schwartzman, as Max, the prep school student who never could say goodbye, became the model for all Andersonian heroes: full of longing, deadpan superiority, innocence, calculation, style, and impeccable timing. It’s a thrilling piece of 90s comedy, the moment when an important contemporary filmmaker planted his flag, and it just gets better with age.
Funniest Moment: “O, r they?”
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25. Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006)
Borat Sagdiyev is Sacha Baron Cohen's greatest character because he makes sure that—as a Kazahkstanian reporter documenting his road trip across America, in which he hopes to abduct and marry Pamela Anderson—for every third world stereotype that he uses, he gets four to five more jokes at the expense of first world Americans. It's a great exchange rate. Borat makes audiences squirm, not because we're not sure how far Cohen will take his visits to rodeos, Civil War antique stores, car lots, and etiquette classes—no, it's because we're not sure much his filmed participants will reveal the homophobic, racist, and classist traits that are more common than we'd like to believe.
Funniest Moment: Borat tries to buy a car by determining how many gypsies he might be able to kill with it, and the salesperson tries to calculate the exact speed that Borat would need to drive to kill the maximum number of pedestrians in his path.
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24. Brain Donors (1992)
Director Dennis Dugan wanted to prove that, as late as the 1990s, the Marx Bros. formula could still work. He and screenwriter Pat Proft paired with John Turturro (the Groucho role), Mel Smith (the Chico role), and Bob Nelson (the Harpo role) to modernize the trio's particular brand of slapstick. While the film bombed and remains in the realm of "cult movie," it was still a round success, capturing the manic Bug Bunny-like absurdity of the 1930s originals, while still being witty unto itself.
Funniest Moment: The final ballet sequence, wherein our heroes interject as gluttons, hunters, ducks, and basektball players.
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23. This Is Spinal Tap (1984)
Never seen it? Doesn’t matter, you’ve still quoted from it even if you weren’t aware that you did. It was from a special time in Rob Reiner’s life when he still made good movies and it stars the best/worst ego-bloated cock-rock band (Christopher Guest, Michael McKean, Harry Shearer) that ever stuffed their spandex leggings. Not long after this film’s release, the classic documentary short Heavy Metal Parking Lot would provide a corollary tale of fandom that, associatively, confirmed every moment of this film as pure, naked truth.
Funniest Moment: Tiny Stonehenge.
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22. The Producers (1967)
Mel Brooks has several films on this list, and few reach the sheer comic naughtiness of The Producers, an impeccably acted farce about a pair of unscrupulous thieves who scheme to raise huge amounts of money for a play they ensure will be a flop. The title characters are the blustering Zero Mostel and his weak-willed assistant, played by Gene Wilder. The Producers would be manic and hilarious if it was just the two of them bantering, but we're also treated to "Springtime for Hitler," a shocking and subversive glee fest about the Third Reich.
Funniest Moment: "Springtime for Hitler," of course.
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21. Top Secret! (1984)
The comedy trio of Zucker, Abrahams and Zucker followed up their smash hit Airplane with an even more absurd spoof, this time mashing up Elvis Presley musicals and Cold War spy thrillers. The result was Top Secret!, starring Val Kilmer as an American crooner (his big hit: “Skeet Surfing”) who falls in with East German rebels and becomes an unlikely hero. Kilmer is a spectacular dork, equally dashing and dumb, and the non-stop onslaught of ridiculous gags has an impressive hit-to-miss ratio. “I know a little German. He’s sitting over there.”
Funniest Moment: Kilmer passes out while being tortured by the Germans, and dreams that he forgot to study for finals. He wakes up, mid-whipping, relieved. "Thank god!"
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20. The Palm Beach Story (1942)
Gerry (Claudette Colbert) loves her husband Tom (Joel McCrea) so much that she wants to leave him and marry a rich guy who will underwrite Tom’s “airport of the future.” Whether or not these two get back together in Preston Sturges’ screwball classic has a lot to do with several very eccentric millionaires, from the hard-of-hearing “Weenie King” (Robert Dudley) to kind-hearted J.D. Hackensacker III (Rudy Vallee), who becomes smitten with Gerry from the moment she steps on his face. (Long story.)
Funniest Moment: Gerry hitches a ride to Florida in a private train car belonging to the Ale and Quail Club; suffice it to say that booze and firearms don’t mix.
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19. Heathers (1988)
In the late 80s, you could still make a comedy about revenge-killing high school bullies and not be called irresponsible. So Daniel Waters and Michael Lehmann gave us a blisteringly, hilariously cruel world of the meanest girls – all named Heather – and their equally popular nemesis, Veronica (Winona Ryder, never better). And then they all died of fake suicides. Then comes the plot to blow up the school. They will never, ever remake this film. Perfection cannot be duplicated.
Funniest Moment: “I love my dead gay son.”
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18. Midnight (1939)
Penniless American Eve Peabody (Claudette Colbert) gets turned into a princess by wealthy Georges (John Barrymore), who wants Eve to distract the gigolo who’s got his sights set on Georges’ wife Helene (Mary Astor). So far so good, until cabbie Tibor (Don Ameche), who’s in love with Eve, shows up to complicate matters. Georges passes Tibor off as Eve’s estranged husband, and then this lunatic farce (written by Charles Brackett and Billy Wilder) is off to the races.
Funniest Moment: The breakfast scene in which Tibor tells their high-society hosts that he and Eve must leave to take care of their ailing daughter, only to have Eve convince them that Tibor’s inbred family is given to delusions. (“Why else should his grandfather have sent me, as an engagement present, one roller skate, covered with Thousand Island dressing?”)
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17. The Big Lebowski (1998)
The Coen Bros.' films were all dryly funny in their own way, but they didn't really go for the comedic jugular until their 1998 stoner opus The Big Lebowski, a straightforward noir story being dimly observed by the laziest man in Los Angeles. Jeff Bridges creates an indelible movie character in The Dude, an old world stoner who has long left ambition behind. This movie is a clever subversion of heroism. What would a movie be like if the protagonist was incapable of any agency?
Funniest Moment: The "Gutterballs" dream sequence.
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16. His Girl Friday (1940)
When people say "they don't make 'em like they used to" in reference to film comedies, His Girl Friday might be Exhibit A. Howard Hawks' film is all quick wit, classy wordplay, perfection of age-old comedic devices (for instance "the rule of three") and a star vehicle (for Cary Grant) that they truly do not make anymore. Plus, even though Grant's Walter Burns thinks there's nothing taboo about divorce—in 1940, there certainly was, and as Burns tries to keep his ex-wife from re-marrying, many audiences had to laugh over the gasps.
Funniest Moment: Curious what "rule of three" means? Watch the two straight guys try to bribe the buffoon (a great Billy Gilbert).
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15. What's Up, Doc? (1972)
Director Peter Bogdanovich’s love of old movies found full fruition in this salute to screwball comedies, starring Ryan O’Neal as a fuzzy-headed music professor from Iowa, helpless before the rapid-fire flirting of Barbra Streisand. A farce built around four identical suitcases, this comedy features wonderfully zany dialogue and one of the great slapstick car chases of all time. This one’s a rare example of the homage being as good (if not better) than the original.
Funniest Moment: Streisand dazzles a dinner party while pretending to be O’Neal’s fiancée, which causes problems when the real one (played by Madeline Kahn, in a brilliant debut) shows up.
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14. Blazing Saddles (1974)
In 1974, Mel Brooks decided to take a sledgehammer to racism and Hollywood mythology in the form of a western. That sledgehammer was made of incendiary comedy that still stings and, 40 years later, might also offend the sensibilities of both conservative and liberal viewers. Of equal importance: the film’s masterful employment of farts. Like a symphony.
Funniest Moment: Any time Madeline Kahn does anything.
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13. Anchorman: The Legend of Ron Burgundy (2004)
Will Ferrell's comedic brand of straight-faced (and oblivious) idiocy is a perfect fit for the 1980s, as it's so easy to look back at popular fashion, items, ideas, and governance during that period and say "go fuck yourself.” And thus, his greatest movie character creation is the maroon-suited Ron Burgundy. Burgundy heads a male staff of local TV anchors who don't believe that women are capable of delivering the news. But the times they are a-changin'. Steve Carell, Paul Rudd and David Koechner all get to play so over the top that it's quite the accomplishment that Ferrell still gets the biggest laughs. Perhaps it’s his attempts at class.
Funniest Moment: Ferrell and Christina Applegate trade barbs while the camera is rolling. It looks friendly at home without sound, even though it ends with "I'll punch you right in the ovary."
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12. Monty Python's Life of Brian (1979)
Monty Python’s vicious skewering of religious fanaticism and ancient Roman history remains as controversial today as it was in 1979, and also just as funny. Graham Chapman headlines as Brian, a poor bastard who was born in the manger just opposite Jesus Christ’s, and whose life falls apart when he joins an anti-Roman terrorist group and gets confused for the Messiah. Jesus actually gets off light in Life of Brian; it’s the maddening world he lived in that gets roasted mercilessly, profanely, intelligently, timelessly.
Funniest Moment: "All right, but apart from the sanitation, medicine, education, wine, public order, irrigation, roads, the fresh water system and public health, what have the Romans ever done for us?!"
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11. Some Like It Hot (1959)
Billy Wilder's drag farce follows two down-on-their-luck musicians who accidentally witness a mob shooting and have to go on the run disguised as women. Not only is there something classical - near Shakespearean, really - about this level of raucous silliness, but Some Like It Hot is also sexually subversive in many ways. Not only do we have a healthy heap of innuendo from the excellent Marilyn Monroe, but the queer themes are right there on the surface. "Why would a guy marry a guy?" "Security!"
Funniest Moment: Nobody's perfect.
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10. Annie Hall (1977)
Annie Hall is a neurotic's diary: it features split-screens, Snow White animations, fourth-wall breaking soliloquies, and a pensive yearning for the one relationship that had a spark, but the writer was too dumb to see it through to the very end. Woody Allen's film is a riotous touchstone ode to the shortcomings of romance, conversation, and friendship that makes us want to continue to engage in all of them. It's Alvy Singer (Allen) and his path to and away from Annie Hall (Diane Keaton).
Funniest Moment: Who hasn’t fantasized about correcting the loud know-it-all in line for a movie (or for that matter, told off internet trolls in person and in public)? If you have, Alvy Singer is a superhero.
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9. The Philadelphia Story (1940)
During the Great Depression, comedies about the silliness of the rich were a weird mix of dreamy aspiration and moral censure. They were rudderless buffoons, those fat cats, and the movies were where we got to mock them. This beloved 1940 George Cukor classic gave the audience Jimmy Stewart as a tabloid journalist avatar to make cutting commentary on the wedding of socialite Katherine Hepburn. Enter Cary Grant as Hepburn’s ex-husband, and Hays Code-approved remarriage rears its sophisticated, witty head. You’ll actually forget you hate the rich.
Funniest Moment: Hepburn and her younger sister pretend to be flighty debutantes, when in reality they’re both almost sinister in their sarcasm.
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8. Playtime (1967)
Writer-director-star Jacques Tati commented on the soullessness of the 1960s by placing his familiar Monsieur Hulot character in a Paris made entirely of steel skyscrapers, one where the Eiffel Tower and the Arc de Triomphe could only be glimpsed as reflections in the glass doors. A virtually silent comedy, featuring a hilarious soundtrack featuring everything from electronics to pillows doing things they’re not supposed to, Playtime is thoroughly modern while pointing out how sterile that modernity can be.
Funniest Moment: An extended scene involving a slowly-crumbling restaurant that probably should have opened one night later.
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7. Groundhog Day (1993)
The key to great comedy is often repetition, and no film puts that theory to the test better than Harold Ramis’s Groundhog Day. Bill Murray stars as a curmudgeonly weatherman who gets stuck in Punxsutawney, PA, and then gets stuck living the same day over and over and over again. First he thinks he’s going mad, then he thinks he’s God, then he thinks he’s in Hell, and then he finally decides to live this one day right. The madcap script is loaded with details, and every single one of them pays off. Usually more than once. Comedies don’t get denser, or funnier, than this.
Funniest Moment: At the end of his rope, Murray decides to kill himself. Again, and again, and again, and again, and again, and...
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6. Ghost Busters (1984)
Ghostbusters paved the way for big, event level comedies that later gave us franchises like Men in Black and 21 Jump Street. But Ghostbusters is so much more than overlord monsters, laser guns, and a giant marshmallow man. It does have all of those big budget motifs, but it also has the type of sly wordplay that wouldn't be out of place in a 1940s comedic caper. It's this familiar wholesomeness that elevates Ghostbusters to icon status: it's just as fun to watch as an adult, as it was when you were a kid.
Funniest Moment: "Are you the Keymaster?"
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5. Monty Python and the Holy Grail (1975)
Leave it to a bunch of Brits who were equally schooled in both medieval history and Theater of the Absurd to craft this scatological, silly and totally brilliant parody of the Camelot legend. Making fun of the pointlessness of grand crusades and adventures, and mocking anyone who would attempt to tell this story on a budget so low that coconut shells substitute for horses, this thoroughly quotable Dada farce destroyed Arthur more thoroughly than Morgan le Fay ever could.
Funniest Moment: The minstrels of the cowardly Sir Robin (Eric Idle) change the lyrics of their ballad to reflect their patron’s lack of bravery.
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4. Duck Soup (1933)
The 1933 Marx Brothers classic isn’t just anti-war, it ridicules the entire enterprise, including “benign” nationalism. There are no ingénues or pointless musical sequences (there are musical sequences, but they’re magnificently insane), and at 68 minutes there’s not a shred of dead weight or moment of dead air. Everything on screen is precisely, perfectly funny, and it can be viewed regularly until the end of your life without feeling like you’ve thrown away another hour and ten. A masterpiece.
Funniest Moment: Groucho and Harpo and a mirror, or at least what Groucho thinks is a mirror. Often imitated, never bested.
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3. Young Frankenstein (1974)
The spoof movie was still new when Mel Brooks decided to parody Frankenstein, but even if it were made today, Young Frankenstein would still represent the apex of the medium. Brooks lampoons every damned part of the Universal Horror model, but unlike some of his later and inferior efforts, he still leaves room for new and unexpected gags. Best of all, his cast is perfect: Gene Wilder as the mad scientist who refuses to admit he’s mad, Marty Feldman as the unflappable Igor (pronounced “Eye-gore”), Teri Garr as the adorable strumpet, Cloris Leachman as the lovelorn servant and Peter Boyle as the monstrous straight man. Let’s just say everyone in this movie deserves to be “elevated.”
Funniest Moment: An honorable mention goes to Gene Hackman's hilarious cameo, but Gene Wilder and Marty Feldman's "Walk this way" gag remains both perfect and timeless.
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2. Airplane! (1980)
This parody of 1970s disaster movies spawned an entire genre of spoofs built upon rapid-fire and often absurd visual and word gags, and none of the films it inspired can touch it for sheer comic brilliance. This was the movie that taught us that the stone-faced dramatic hams of yesteryear (Lloyd Bridges, Robert Stack, Leslie Nielsen) can be the greatest comedians — just don’t call them Shirley. Thirty-five years later, Airplane! still soars high above the competition.
Funniest Moment: A singing stewardess emulates Helen Reddy in “Airport ’75,” but watch out for that IV line.
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1. Dr. Strangelove, or: How I Learned to Stop Worrying and Love the Bomb (1964)
Of all the films on this list, Stanley Kubrick's Dr. Strangelove, or: How I Learned to Stop Worrying and Love the Bomb is perhaps the most salient. Despite having been made during the first generation of nuclear scares (and we've indeed had a few since), it still seems timely in every era, poking naughty fun at the way nations bandy about the destruction of the human race with a distressing flipness. It feels like a farce, but it's also all too real. This movie is hilarious, and it is chilling, and it is excellent. Mein Fuhrer! I can walk!
Funniest Moment: When George C. Scott trips and flips over backward. "Mr. President! They're gettin' ready t' clobber us!"
