70 Greatest Comedies of the 21st Century

It’s high school as hierarchical hell, a world full of J.V. jocks and girls who eat their feelings, desperate wannabes and burnouts – and the Plastics, led by Queen Bee Regina George. Tina Fey established herself as one of America’s best comedy writers courtesy of this instant teen-movie classic, which boasts one of the most quotable scripts of the past 20 years (“Stop trying to make ‘fetch’ happen”; “Boo you whore”; “On Wednesdays we wear pink”; “If you’re from Africa, why are you white?”) and will forever endear Lindsay Lohan to us no matter what. While the portrayal of popularity borderline satirical, the laughter comes with a bit of a sting – it’s a peerless reminder of how funny and how shitty your teen years were. KYK

Ben Stiller’s 2008 Hollywood burlesque is so spot-on, he even gets the right studio logos for the opening’s fake trailers. (Why yes, the indie tortured gay-monk drama would be a Fox Searchlight release.) A film’s cast and crew is stranded in the jungle when an Apocalypse Now-style war movie runs awry — at which point this satire mercilessly punctures the egotism, marketing and jargon of movie stardom, with plenty of residual bile for the cogs of the studio machine. The ensemble cast is a who’s who of comic firepower, with Robert Downey Jr. as a ridiculously extreme Method actor and Tom Cruise (nearly unrecognizable under pounds of make-up and a bald cap) as a crass, loathsome executive both vying for MVP status. JBa

Taika Waititi and Jemaine Clement’s macabre mock doc about vampires is great PR for creatures of the night and the perfect introduction to New Zealand’s deader-than-deadpan humor — a wonderfully inane strain that thinks nothing of blending gory set pieces with po-faced reaction shots to the camera and plenty of stealth quotables. (“We’re werewolves, not swear-wolves.”) As this houseful of bloodsuckers bickers, blusters and try not to wake up an 8,000-year-old roommate, the filmmakers keep mining every nook and cranny of his premise for laughs, and with a $1.6 million budget, this comedy squeezes in more jokes-per-dollar than every other film on the list. You can see why Marvel felt confident in letting Waititi wreak humorous havoc with a Thor-in-outer-space movie. The TV show is equally as brilliant, but the original is still worth its weight in delicious Type O. AN 

It’s easy to make a high school movie that’s funny; it’s significantly trickier to make one that also feels true. Greta Gerwig’s solo directorial debut doesn’t get its laughs from outsize gags or teens spewing dialogue so clever that it could only have been written by a 45-year-old. In fact, the Sacramento Catholic high school circa 2002 where Christine “Lady Bird” McPherson (Saoirse Ronan) matriculates seems so real that you can practically smell the acne cream — and therein lies the humor. Everything our heroine experiences in her senior year — from a bizarre teen Sondheim production to mother-daughter dress shopping to dumb crushes and disappointing sex — cracks us up in only the way that something like a memory can. JS

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

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

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’swhere 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

Two years removed from his triumphant Saturday Night Live run, Will Ferrellcemented his transition to movie stardom (already in full swing thanks to Old School and Elf) with this masterstroke of absurdist, blowhard comedy. In RonBurgundy, Ferrell and his frequent collaborator/director/co-writer AdamMcKay found the perfect delivery device for the actor’s hilarious sendup ofalpha-male privilege, playing the buffoonish, sexist San Diego newscaster whosecocksure reign is about to be punctured. It helped also established Ferrell’s brilliant non-sequitur oddness: How a bull session aboutlove segues inexplicably into an impromptu acappella 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

“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

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

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

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

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

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

“You’re gonna have to give him a moment, son. Dewey Cox has to think about his entire life before he plays.” Jake Kasdan’s merciless takedown of the modern music-biopic formula remains the final parodic word on the subject; you picture him and producer/cowriter Judd Apatow compiling a genre checklist and just skewering each entry one by one. The childhood trauma (“The wrong kid died!”), the do-or-die discovery of a hit single in the recording studio, the rocky marriages, the muse, the rise, the fall, the sex, the drugs, the experiments with theremins, the pet monkeys and the phoenix-like comeback — it’s a roll call of 20th century musical-genius clichés taken to sublimely ridiculous extremes. The fact that John C. Reilly nails a host of hard-singin’, hard-playin’ styles from early rock ‘n’ roll to outlaw country & western to Pet Sounds-level excess — we personally have a soft spot for Dewey Cox’s brief but unforgettable Dylanesque phase — only sweetens the deal. (Not to mention that the particular way he says “cu-caiine” is the icing on the fake-superstar cake.) Everybody from The Office‘s Jenna Fisher to Tim Meadows hits their beats perfectly, though a hearty shout out goes to the Cox superfan who we’re told moonlights as musician himself.—D.F.

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

Will Ferrell is at his funniest when he’s got a tag-team partner (see: Anchorman, The 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