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50 Greatest Comedies of the 21st Century

From rom-coms to raunch-coms, ‘Anchorman’ to ‘Wet Hot American Summer’ – the funniest movies of the new millennium so far

50 greatest comedies

What’s so funny? If you’re talking about screen comedy in the 21st century, the answer is easy: bumbling manchildren, the more boorish and clueless and stuck in their stunted adolescence, the better. Talking foxes, Huey Lewis-loving serial killers, world-saving marionettes, foul-mouthed political fixers and boisterous bridesmaids – all great as well. German father-daughter duos and goofy stoners? Bring ’em on! Headbanging teachers and backstabbing bureaucrats? Yes, we’ll take them too.

Since the turn of the century, we’ve giggled at the poignant and the perverse, rom-coms and raunch-coms, new-and-improved takes on singular comic types and loose, highly improvised ensemble pieces that spread the spotlight around. Some of these movies have been gently witty, while others have displayed all of the subtlety of a dose of Sex Panther cologne. But they’ve all consistently cracked us up, in a near–two-decade span in which – let’s be honest – we’ve need a laugh or two. Or three. Or a dozen.

After a number of heated arguments and lots of name-calling and the occasional chaotic pie fight, we’ve narrowed down our choices for the greatest comedies of the 21st century. Culling this down to a mere 50 entries was a tough call – humor is a seriously subjective topic, and every one of our 19 writers weighing in had their own idea of what constitutes “hilarious.” But this list represents the best cross-section of screen comedy of our still young millennium, a collection that runs the gamut from droll to bladder-loosening. Given the high possibility of sidesplitting, you may wanna have a medical professional on hand. And don’t forget to stay classy, San Diego.

'A Serious Man' (2009)

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15

‘A Serious Man’ (2009)

Joel and Ethan Coen make their most personal film yet, a unsettlingly uproarious Job parable set in their Minnesota hometown of St. Louis Park and its tight Jewish community. A put-upon physics professor up for tenure watches his marriage falls apart, while his cyst-suffering, Mentaculus-obsessed brother is wanted by the police and his reefer-loving son preps for an upcoming Bar Mitzvah. But the real subject is an unjust universe, where Heisenberg’s uncertainty principle and Schrödinger’s cat only deepen the mystery of a life rife with obtuse rabbis, fuzzy F-Troop reception and dogged calls from the Columbia Record Club. A Rosetta Stone for deciphering the filmmakers’ signature brand of empathetic nihilism and its place in the Judaic storytelling tradition, A Serious Man mixes cringe-worthy comedy with caustic insights about the struggle for meaning in a naggingly enigmatic world. SG

'Everybody Wants Some!!' (2016)

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14

‘Everybody Wants Some!!’ (2016)

For this “spiritual sequel” to his spirit-of-’76 classic Dazed and Confused, Richard Linklater captured another turning-point moment in the lives of some young Texans. Instead of the last day of high school in our nation’s bicentennial year, we ride shotgun with some baseball players during the first weekend of college circa 1980. Over a drunken stretch of days, a group of jocks and other early arrivals play scarily aggressive games of ping pong, attempt stoned telepathy, share favorite Twilight Zone episodes, line dance, slam dance and otherwise get to know each other while trying to figure out who they’ll be for the next four years. It’s rowdy fun even as Linklater keeps offering reminders that the good times won’t last forever. KP 

'The Death of Stalin' (2017)

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13

‘The Death of Stalin’ (2017)

It’s a hilariously corrosive concept: Oddballs like Steve Buscemi, Simon Russell Beale, Jeffrey Tambor and Michael Palin act out the politburo power
struggle that emerged in the wake of Joseph Stalin’s demise in 1953, practically tripping over the corpse to ensure a seat at the head of table. Sure, it sounds like an episode of Drunk History, but writer-director Armando Iannucci
manages to craft spit-worthy dialogue while making it very clear that lives are
at risk. Some of the material is innately ridiculous – Stalin’s
deadbeat son (Rupert Friend) berating a hockey team, for instance – but it’s
where the comedy of errors gets brutal that the satire truly earns its bones. To quote Buscemi’s Nikita Khrushchev: You laugh so you don’t get shot. EZ

'Anchorman'

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12

‘Anchorman’ (2004)

Two years removed from his triumphant Saturday Night Live run, Will Ferrell
cemented his transition to movie stardom (already in full swing thanks to Old School and Elf) with this masterstroke of absurdist, blowhard comedy. In Ron
Burgundy, Ferrell and his frequent collaborator/director/co-writer Adam
McKay found the perfect delivery device for the actor’s hilarious sendup of
alpha-male privilege, playing the buffoonish, sexist San Diego newscaster whose
cocksure reign is about to be punctured. It helped also established Ferrell’s brilliant non-sequitur oddness: How a bull session about
love segues inexplicably into an impromptu a
cappella performance of “Afternoon Delight,
” or how a rivalry with other news crews effortlessly turns into a Warriors-style street brawl. And it’s quotable as hell, from Burgundy’s declaration that San Diego is German for “a whale’s vagina” to his insistence that he’s “in a glass case of emotion.” In the not-too-distant future, we’ll all be speaking in Burgundy-isms. TG

'In Bruges'

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11

‘In Bruges’ (2008)

“Maybe that’s what Hell is: the entire rest of eternity spent in Bruges.” So says Colin Farrell in Martin McDonagh’s feature-length debut, which is to so-called “dark” comedies what a black hole is to turning off your bedside lamp. The award-winning playwright-turned-filmmaker manages to extract humor from such noted comedic touchstones as accidentally killing a child, Belgian tourist destinations and Ralph Fiennes in a frothing rage – and infuses it all with the deft, distinct sense of morality he had polished over his years with his stage work. And whether you loved or hated Three Billboards Outside Ebbing, Missouri, it’s hard not to pine for the days when McDonagh’s dialogue was being read in Irish accents, particularly when one of those accents belongs to Brendan Gleeson. KL

'State and Main' (2000)

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10

‘State and Main’ (2000)

Writer-director David Mamet’s spirited showbiz satire skewers Hollywood pretension, casting a pre-30 Rock Alec Baldwin as a vain, lecherous movie star who gets into trouble when his latest over-budget production rolls into a sleepy Vermont small town. A crude, pushy director (William H. Macy), a sad-sack screenwriter (Philip Seymour Hoffman), and an emotionally fragile leading lady (Sarah Jessica Parker) take turns getting fleeced by not-as-innocent-as-they-look locals, as Mamet makes his version of a fast-paced backstage farce. State and Main is both savage and silly, a genius riff on the chutzpah of the rich and famous filled with hep, imaginatively vulgar lines: “Who designed these costumes? It looks like Edith Head puked, and that puke designed these costumes.” NM

'The 40 Year Old Virgin' (2004)

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9

‘The 40 Year Old Virgin’ (2005)

Judd Apatow had already made a name for himself with small-screen sketch comedy (he co-created The Ben Stiller Show), peerless cringe-comedy (The Larry Sander Show) and sensitive character-based comedy (R.I.P., Freaks and Geeks). For his big-screen directorial debut, he took a bit from all three and concocted what’s become a modern-comic urtext: the heavily improvised, ensemble-cast manchild farce. A post-Daily Show/pre-The Office Steve Carell is the title character, a geek-culture lifer who’s never had a real relationship; a crack team of supporting players including Romany Malco, Jane Lynch, Seth Rogen and Paul Rudd offer horrible romantic advice and off-the-cuff riffs about everything from soft rock to skin-mag stashes. (Seen today, the Rudd/Rogen volley of absurd “you’re gay” playground taunts is somehow both a highlight and a low point.) The talent bench is deep here – blink and you’ll miss Kat Dennings, Mindy Kaling, Jonah Hill and Kevin Hart in small parts – while Apatow’s knack for connecting outrageous set pieces with a surprisingly overall sweetness would become his signature. But it starts here, and as everyone knows, you never forget your first time. DF

'Shaun of the Dead'

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8

‘Shaun of the Dead’ (2004)

Best spoof of the century? Director Edgar Wright’s breakthrough film takes the piss out of horror movies, zombie flicks and post-apocalyptic dramas – and then, because he’s such a clever lad, still delivers a pretty riveting mash-up of those styles on top of it. Shaun of the Dead is really funny and really frightening, with each tone enhancing the other; co-writer Simon Pegg’s ordinary bloke is so bored by modern life that he doesn’t initially realize that the walking dead have invaded his town. You can see the early stages of the cheeky, stylish irreverence that would become the British filmmaker’s trademark, as well as generating tons of laughs from the dim-bulb rapport of Pegg and Nick Frost’s clueless characters. It’s so hilarious, in fact, that it takes a moment to realize how weirdly emotional it can be, too. The end of the world – somehow sidesplitting and touching. TG

'Toni Erdmann'

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7

‘Toni Erdmann’ (2016)

Unlikely as it may seem, one of the greatest comedies of the last two decades is a 162-minute movie from Germany. Writer-director Maren Ade spends most of that runtime testing the fragile bond between the two leads: corporate drone Ines Conradi (Sandra Hüller) and her incorrigible-prankster dad, Winifred (Peter Simonischek), who follows her on a business trip to Bucharest. When they inevitably fall out, he puts on a bad wig and re-enters her life as a boorish life coach named Toni Erdmann. Awkward exchanges, sweet father-daughter bonding and scenes that suggest serious undertones of feminist workplace frustration follow. The ending is legitimately profound, but Ade doesn’t just traffic in droll European humor. The triple whammy of karaoke, comic nudity and costumed lunacy that dominate the final hour is on par with anything in the Apatow universe. JBe

'Punch Drunk Love'

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6

‘Punch Drunk Love’

What did Paul Thomas Anderson see in Adam Sandler that nobody else had when he cast him as a lonely Los Angeleno? The answer: A rage that was never far from the surface of the comedian’s manchild characters. The filmmaker teases Sandler’s sound and fury out via a love story in which San Fernando Valley businessman Barry Egan falls for Lena (Emily Watson), a friend of one of his many sisters. They’re two misfit people who clearly belong together, even if his habit of bottling his ire until it explodes threatens both their relationship and the bathrooms of local restaurants. Also, did we mention the Provo, Utah phone-sex operators and Philip Seymour Hoffman’s vengeful mattress king? The film served as a kind of coming out for Anderson, who shook off the influences of his first films to get looser, stranger, more heartfelt and way funnier than he’d ever dared be before. KP

'Idiocracy'

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5

‘Idiocracy’ (2006)

It took approximately six million years for humans to evolve from their apelike ancestors, but only about a decade for them to devolve more or less as Mike Judge’s satire predicted. Idiocracy takes place 500 years into the future, when colossal dumbasses have their lard-greased paws on all the levers of power and farms are irrigated by a popular sports drink. (“Brawndo: It’s What Plants Crave!”) Fox left the film for dead in theaters – it had no trailer, didn’t screen for critics and made less than half a million at the box office – but now it’s the go-to comedy of the Trump Era, a fun place to laugh about the dystopic trash pile that currently engulfs us. (If the current Secretary of Agriculture starting pumping Gatorade in fields throughout the Heartland, would he even lose his job?) ST

'Step Brothers'

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4

‘Step Brothers’ (2008)

Will Ferrell is at his funniest when he’s got a
tag-team partner (see: AnchormanThe Other Guys) – but Step Brothers is, hands down, his best double act. Working alongside Talladega Nights chum
John C. Reilly, the duo play stunted adults forced into the same family when
their single parents (Richard Jenkins, Mary Steenburgen) remarry. They’re are the extreme edge of the bozo manchildren that made Ferrell a superstar and Reilly his goofball screen soul mate – it’s their back-and-forth idiocy that makes this a modern classic. And once
you’ve fully absorbed the brilliance of their interplay, be sure to spend
a little time marveling at the movie’s murderers’ row of ensemble players, including a perfectly repugnant Adam Scott and Kathryn Hahn as a horribly horny
wife. You’ll never hear “Sweet Child o’ Mine” the same way again. TG

'Bridesmaids'

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3

‘Bridesmaids’ (2011)

Champagne and cupcakes and party favor puppies wrapped up with string – Kristen Wiig throwing tantrums is our favorite thing. Decades from now, it’ll be clear that this story about a thirtysomething stuck in a rut and her fellow bridesmaids (the XX-chromosome counterparts to Judd Apatow’s stable of male kooks and losers) was a magic bean sprouting the future of studio comedies. Fresh faces like Rebel Wilson, Ellie Kemper, Chris O’Dowd and shock Oscar nominee Melissa McCarthy get plenty of room to make an impact; Wiig, fellow SNL vet Maya Rudolph and sly comic MVP Rose Byrne prove they’re superstar material. Proudly feminine and patently successful, this ensemble raunch-com celebrates the inner paranoia and outer politeness of best frenemies, all hugs with fingernails filed to a shiv. (And the there’s the instantly classic food-poisoning scene – who didn’t snort so hard their popcorn went flying?) Every studio wanted to copy it. None of them dared, which gave director Paul Feig years to dominate the no-fuck’s-given female blockbuster lane. Thanks to the seed Bridesmaids planted, now that turf is more crowded. AN

'In The Loop'

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2

‘In The Loop’ (2009)

Armando Ianucci’s bitter, foul-mouthed political satire about the Byzantine backroom back-and-forth between the U.S. and the U.K. in the run-up to a new war had a bitter ring of truth about it when it was released: The conflicts in both Iraq and Afghanistan were raging; the Bush administration was sword-rattling about Iran; and the future Veep creator’s distressingly plausible comedy demonstrated how terrible decisions could be made through a combination of ineptitude, spite and cover-your-ass cowardice. (The writer-director did his homework for this movie; he even famously broke into the U.S. State Department for research, which may have prompted new security protocols.) Seen now, this portrait of bureaucracy and institutional loyalty seems almost quaint – and yet, somewhere in there, amid the madness and nonstop motormouthed insults, Ianucci also gets at a powerful, prophetic truth: That in a world of rampant spinelessness, the cruelest man is king. BE

'Best in Show' (2000)

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1

‘Best in Show’ (2000)

The greatest comedy of the 21st century directly descended from one of the best of the 20th. Some 16 years after co-writing and starring in This Is Spinal Tap, Christopher Guest made this other milestone mockumentary – a flawless and deliriously executed work that transforms spoofery into something sublime. From Eugene Levy’s buck-toothed, two-left footed cuckold to Jane Lynch’s super-competitive trainer, every caricature miraculously becomes a sympathetic character, one deadpan line at a time. On the way to a competitive dog show, canines play straight men while their handlers run amuck. And then, halfway to the end, Fred Willard shows up and steals the show as a borscht belt TV commentator, delivering hoary one-liners so rapidly that you can barely catch your breath. No matter how ridiculous it all was, you walk away from Best in Show feeling that you’ve spent 90 minutes watching real people – and that comedy can carry the weight of our truly absurd lives. EH     

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