Maybe with everything going the way it is in the world right now, we’re laughing in hopes of keeping less cheery emotions at bay. At least this bizarre, still-very-much-in-progress century has already produced any number of great comedies that you can fire up any time you need a serotonin burst, thanks to the ever-growing cadre of streaming services. As the pandemic continues to drag on, we thought it was more important than ever to give our Greatest Comedies of the 21st Century list, originally published in 2017, a rethink.
About half of the list that appears below is entirely new. We dropped a number of titles from the original list that are funny, but not necessarily comedies. And we’ve added some titles released since 2017 that needed to be included, plus a handful of films released before then that the staff at IndieWire have deemed essential. As IndieWire has evolved, so has this list, and it will continue to do so as long as we keep finding films that make us laugh.
“50. Neighbors” (2014)
Like his master teacher Judd Apatow on “Freaks and Geeks,” “Knocked Up,” “Superbad” and “Pineapple Express,” Seth Rogen is a multitasker: he writes, acts, produces and directs. He and partner Evan Goldberg developed and produced “Forgetting Sarah Marshall” director Nicholas Stoller’s raunchy, R-rated “Neighbors,” a well-constructed contemporary slapstick comedy costarring Rogen and “Bridesmaids” star Rose Byrne as hip young parents with an adorable baby. They’ve never been funnier. When a raucous fraternity house dominated by well-muscled ringleader Zac Efron move in next door, the neighbors initially seek to get along, but are soon engaged in all-out war. —Anne Thompson
Rent or buy on Amazon.
49. “Support the Girls” (2018)
In yet another reminder of how amazing an actress she is, Regina Hall plays the general manager of a Hooters-like breastaurant called Double Whammies in Andrew Bujalski’s “Support the Girls,” an earnest ensemble comedy about working-class women supporting one another while avoiding lecherous men, a rival chain (ManCave), and trappings of late-stage capitalism. A film that unfurls at its own pace and rewards multiple viewings, the real treat of “Support the Girls” is watching the aforementioned ensemble (most notably Hall’s Lisa, Haley Lu Richardson’s Maci, and Shayna McHayle’s Danyelle) navigating both the service industry and their own lives. —Leonardo Adrian Garcia
48. “One Cut of the Dead” (2017)
A low-budget, high-concept work of tongue-in-cheek genius, Ueda Shin’ichirô’s “One Cut of the Dead” is hands down the best zom-com since “Shaun of the Dead” viralized the sub-genre. Unfolding like some kind of unholy cross between “Day for Night” and “Diary of the Dead,” Ueda’s self-reflexive delight honors and humiliates zombie cinema in equal measure (and also in that order). The infectious fun begins with a virtuosic but strangely casual 37-minute long-take that messes with your expectations from start to finish, as an actor on the set of a horror movie confuses a real zombie for a member of the cast. You might think you know where things are going from there, but trust us — you don’t. Drunk on its own DIY energy and deeply in love with everything it’s doing, “One Cut of the Dead” is a euphoric ode to the chaos (and compromises) of genre filmmaking; it’s the kind of movie that makes you want to pick up a camera, call some friends, and die laughing as you shoot the end of the world on your own terms. —David Ehrlich
47. “The 40-Year-Old Virgin” (2005)
As smooth as a bag of sand, Judd Apatow’s first feature remains his best (sorry, “Knocked Up”). The sweet-but-vulgar formula it helped popularize has been imitated countless times in the decade-plus since its release, but never fully replicated — Steve Carell’s charming naivete alongside the improvisatory crudeness of Paul Rudd, Seth Rogen and Romany Malco made for a perfect balance. Also: Catherine Keener, whose warm presence helped make this more than just a series of improvised dick jokes. —Michael Nordine
Rent or buy on Amazon.
46. “Barbershop” (2002)
Tim Story’s franchise-starting 2002 hit couches itself in formula to deliver a unique slice of life that’s as funny as it is heartfelt. Bolstered by strong performances by a wildly stacked cast, including Ice Cube, Michael Ealy, Eve, Cedric the Entertainer, Keith David, and Anthony Anderson, the smash hit may have kickstarted an entire series, complete with spinoffs and TV shows, but even as its own entity, it’s a worthy entry into the commercial comedy hall of fame. Specificity helps drive that appeal, as does a storyline with real stakes, all of which Story and his cast weave together with ease. What’s better than sitting back and taking in the gossip and gags at the local barbershop? —Kate Erbland
45. “Adaptation” (2002)
The ultimate in “don’t try this at home” screenwriting, Charlie Kaufman’s deliriously self-reflexive twist on Susan Orlean’s “The Orchid Thief” is so clever and bittersweet that it can be easy to forget how funny it is; between two Nicolas Cages, a homicidal Meryl Streep, and a quick look at the birth of the universe, the hilarity of something like Donald Kaufman’s pitch for “The 3” (“it’s like a battle between motors and horses”) tends to be engulfed by the anxiety that surrounds it on all sides. But much like the film’s dual protagonists, the despair in “Adaptation” is twinned with hilarity, and director Spike Jonze pushes those polarized energies toward each other until they erupt into an unhinged third act that giddily embraces all the things that Kaufman was laboring so hard to avoid. Few movies have ever found such exciting ways to have their cake and eat it too, and even fewer have been able to wring so many laughs from how bad they would’ve been if everything hadn’t gone wrong. —David Ehrlich
44. “Sideways” (2004)
Many accoutrements pair well with “Sideways” — fine cheese, grapes, existential dread — but one most certainly does not: fuckin’ Merlot. Led by one of the greatest performances to ever go un-nominated by the Academy (snub of all snubs!), Alexander Payne’s wine-drunk dramedy is, like any good glass of vino, likely to inspire buzzed introspection and giddy laughs in equal measure. Paul Giamatti is almost-middle-aged ennui personified, with Thomas Haden Church as his unfaithful sidekick; though steeped in melancholy, their raucous last hurrah in wine country is a celebration for the ages. —MN
Rent or buy on Amazon.
43. “Greener Grass” (2019)
The world of “Greener Grass” feels so real and so recognizable, even as it becomes more and more layered with absurdities that make it feel alien. It’s like Wes Anderson taking on a “Black Mirror” installment, or the David Lynch of “Wild at Heart” suddenly directing an episode of “Desperate Housewives.” Yet it’s all original, and it’s given to us by two ingenious comedians in their feature film directorial debut: Jocelyn DeBoer and Dawn Luebbe.
IFC Midnight snatched up “Greener Grass” out of Sundance 2019: it’s the definition of a midnight movie. Two housewives are best pals in a suburban neighborhood where everyone wears pastels and engages in vicious one-upsmanship — until one decides, according to what you’ll find is a logic unique unto “Greener Grass,” to give her baby to the other as a gift. Then another child suddenly turns into a dog. It’s a satire of keeping up with Joneses unlike anything else. Well, maybe not quite. Love all that stuff with Kyle MacLachlan as Dougie and Jim Belushi as the gangster in “Twin Peaks: The Return”? Imagine an entire movie of that. As singular and stylish a movie as that sounds, “Greener Grass” is, above all, funny. It’s the hardest this writer has ever laughed at Sundance. —Christian Blauvelt
42. “Dear White People” (2014)
Justin Simien’s feature directorial debut “Dear White People” heralded many things in 2014: First, the arrival of a major new Black — and queer! — voice in American cinema. Second, an incisive look at the fractious insides of a prestigious Ivy League university through different-colored lenses. And third, it sparked the launch of a hugely popular Netflix series based on the movie in 2017. This U.S. Special Jury Award winner out of the Sundance Film Festival introduced a number of now-massive talents just getting their foot into Hollywood’s door at the time, including Tessa Thompson as a conflicted activist and radio host, and Teyonah Paris, who later starred in “Chi-Raq” and “If Beale Street Could Talk” before, like Thompson, entering the MCU. Even as an incisive look at the racist transgressions within the posh school of Winchester, the film is flat-out funny, and buoyed by its winning ensemble. —RL
41. “Kung Fu Hustle” (2004)
The worldwide success of “Crouching Tiger, Hidden Dragon” paved the way for a flurry of wuxia movies in the early aughts (what a time to be alive!), and while most of them offered high-flying displays of the martial artistry that has sustained the genre for so many decades, few were as spirited as Stephen Chow’s “Kung Fu Hustle,” and none were as funny. Wielding big laughs and cartoonishly bad CG with the precision of a katana — or at least a giant axe — Chow’s period extravaganza re-envisioned 1940s Shanghai as part Shaw brothers and part “Looney Tunes,” the filmmaker starring alongside Lam Chi-chung as a pair of petty crooks who dream of joining the violent gang that runs their town with an iron touch.
The premise lends itself to all sorts of mischievous hijinx (the hero’s frustrated attempt to rob an ice cream vendor is tragicomedy at its finest), but it’s during the fight scenes that “Kung Fu Hustle” achieves some kind of enlightenment. For pure laughs it’s tough to beat the bit where two guzheng-wielding assassins use the power of music to kill a trio of kung fu masters, only to be defeated themselves by a cigarette-puffing landlady who saunters downstairs and casually reduces everyone to ash without mussing the curlers in her hair. Pure cinema. —DE
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