With everything going the way it is in the world right now, we’re laughing to keep 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. The pandemic may be starting to recede but the specter of war and a tortured economy have occupied our minds instead: so, in desperate need of some humor, we thought it was more important than ever to give our Greatest Comedies of the 21st Century list, originally published in 2017 (and last updated in August 2021), a rethink.
We’ve added 25 new films to the Top 50 list we unveiled in August. At that time, 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. (Here’s lookin’ at you, “The Lobster.”) 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.
With editorial contributions from Christian Blauvelt, David Ehrlich, Kate Erbland, Leonardo Adrian Garcia, Eric Kohn, Ryan Lattanzio, Michael Nordine, Chris O’Falt, Zack Sharf, and Anne Thompson.
75. “Good Boys” (2019)
Just think: Your favorite Judd Apatow comedy is scaled down and all those raunchy jokes are coming out of the mouths of tweens. Sure, it may sound gimmicky but “Good Boys” is anything but a typical tween movie. Jacob Tremblay hilariously leads the R-rated middle school comedy about growing up and growing out of his Beanbag Boys childhood friend group. From first kisses to flying drones, riding bikes to the mall to selling a sex doll, “Good Boys” doesn’t hold back for its laughs, and each joke is equally as adorable thanks to the ensemble cast including Keith L. Williams, Brady Noon, Lil Rey Howery, Will Forte, and Molly Gordon. Seth Rogen and Evan Goldberg produced the directorial debut from “The Office” writers Lee Eisenberg and Gene Stupnitsky, who also co-created Stephen Merchant’s “Hello Ladies” series. No matter how bad these middle school boys are, they will always be “Good,” if not even great. Did “Good Boys” singlehandedly resurrect the R-rated tween movie? We might dare to say so. —SB
74. “Bend It Like Beckham” (2003)
The David Beckham references — from the title to a winking inclusion of the man himself during the film’s final feel-good moments — might feel a bit outdated, but Gurinder Chadha’s winning rom-com remains as warm and uplifting as it was when Becks was scoring goals at Old Trafford. The warm-hearted film goes beyond the pitch as it delves into the plight of Punjabi Sikhs in England and other issues of the day — all while maintaining a loose spirit that keeps it firmly in the comedic realm.
Parminder Nagra and Keira Knightley, both in star-making roles, make for great teammates and even better castmates, keeping things fleet of foot even as they and their director ensure that “Bend It Like Beckham” is never a mere trifle. Chadha, who grew up in London as part of the Indian diaspora, finds both pain and beauty in her heroine’s attempt to please her traditional parents while forging her own dual identity, a wonderful balancing act between tones that never robs the film of its charm. —KE
73. “Crazy Rich Asians” (2018)
The broad strokes of Kevin Kwan’s bestselling, compulsively readable “Crazy Rich Asians” novel are familiar enough: it’s a girl meets boy story — and a girl-meets-boy’s-deranged-family story — the kind of subject matter that’s always ripe for a comedy. But Kwan’s books, loosely based on his own coming-of-age in Singapore, take that classic narrative and turn it into a vivacious love letter to contemporary Asian culture, populated by unique characters and set in the eye-popping locales of Singapore, one of the world’s richest countries.
Jon M. Chu’s big screen adaptation of the material, a groundbreaking studio film that is entirely populated by Asian-American performers (the first of its kind at the time since “The Joy Luck Club,” 25 years prior), is a loving take on Kwan’s books, bundled up in a wildly entertaining package. It’s the chemistry among the cast that gives the film its comedic power, be it the back-and-forth zaniness between Constance Wu and Awkwafina or the delightful menace that Michelle Yeoh wraps every line of dialogue. Smiling through every scene is the baseline viewing experience for “Crazy Rich Asians,” which means the cast has you right in the palm of their hands when it’s time to land a joke. As far as contemporary romantic-comedies, “Crazy Rich Asians” is the most irresistible. —ZS
72. “Bad Luck Banging or Looney Porn” (2021)
Radu Jude’s “Bad Luck Banging or Loony Porn” begins as the story of a sex tape gone wrong, with circumstances unfolding at the center on the restless streets of Bucharest, as the frantic problems of a schoolteacher and the community divided against her take place against much larger concerns. As the situation bubbles up to a conclusion, Jude unleashes three very different endings to Emi’s situation — and it’s the third, craziest possibility that makes this entire strange endeavor worth the wait: It all comes down to a John Waters-like eruption of grotesque rage and outré wish-fulfillment that works on too many levels to spoil here, except to say that they involve a jarring fantasy of female empowerment never put to screen before. —EK
71. “Chicken Run” (2000)
Aardman Animations’ first feature-length film does plenty to remind viewers of the delirious charms of the stop-motion animation realm and the wacky minds behind it. A feather-rustling, egg-shaking, weirdly very human adventure film, Peter Lord and Nick Park’s comedy follows a group of farmed chickens on the run after they realize — uh, what now? — that they’re about to be turned into meat pies.
It’s a classic story, gussied up with more bird-brained humor than you can shake a chicken coop at, and with all the warmth and love that always runs through Aardman’s work. Care about chickens? How can you not after watching this zippy little slice of feel-good family action. (Apologies to anyone who had to answer some massive questions about the ethics of eating animals after showing this to the young ‘uns, but hey, comedy can be teachable too.) As of last June, a long-rumored sequel seemed to finally be readying to hustle its feathers onto the big screen, thanks to Netflix and Aardman’s continuing production pact. —KE
70. “Wild Tales” (2014)
Damian Szifron’s Argentine ode to the messiness of life bears the quicksilver changes in tone that define the best work of Bong Joon Ho. But this fearless, riveting collection of six Spanish-language short films underlines something else: the precision needed to do comedy well — to have kinesthetic mastery over your audience’s nervous systems — is the exact same as that needed to do suspense and horror. One short, about a road rage incident that spirals out of control toward such extremity that laughter is only end-response, particularly captures that. As does the very first installment, “Pasternak,” in which everyone aboard a flight discovers that they know the same person. White-knuckle terror and punchlines can be one and the same. And the final short, a wedding that spirals into accusations and infidelities while the reception guests are still partying, takes cringe comedy to its absolute limit.
The ultimate in “laugh because you don’t know how else to feel” movies, “Wild Tales” is also a showcase for storytelling economy and punch characterizations. An ex-con’s response when asked why she went to jail? “Doing nothing I regret.” No exposition could be better than that. And the fact that, seven years after “Wild Tales,” Szifran finally has a follow-up in the can, his English-language debut “Misanthrope,” should give us hope that we can be as thrillingly uncomfortable again soon. —CB
69. “Bad Grandpa” (2013)
©Paramount/Courtesy Everett Collection
Johnny Knoxville’s prosthetic immersion into playing naughty grandpa Irving Zisman was so impressive that makeup artist Stephen Prouty earned an Oscar nomination at the 86th Academy Awards. This typically raunchy “Jackass” spinoff entry directed by Jeff Tremaine follows Irving and his impressionable grandson (Jackson Nicoll) on a cross-country road trip that pairs them with society’s sleaziest and most unexpecting. Cameos from “Jackass” behind-the-scenes alum Spike Jonze and even Catherine Keener (though left on the cutting room floor) make for another hilarious experience that pushes the edges of good and bad taste. —RL
68. “World’s Greatest Dad” (2009)
©Magnolia Pictures/Courtesy Everett Collection
“World’s Greatest Dad” sits next to “Four Lions” in the pantheon of recent films that turned the most unfunny subjects on the planet into indisputable comedy gold. Not every film could find a way to tell a touching and genuinely funny story about suicide, but not every film has the talents of Robin Williams at its disposal either. When Williams’ son dies in an embarrassing sexual accident, he does one last act of good parenting by trying to hide the details in a way that leads to his son’s memory becoming more beloved than it ever would have been otherwise. The material is an excellent showcase for both Williams’ comedic and dramatic chops, and manages to fearlessly look at the bizarre nature of posthumous celebrity worship without ever seeming tasteless. While the subject matter of “World’s Greatest Dad” has taken on a much sadder context in the wake of Williams’ tragic suicide, that is no reason not to appreciate the brilliant work that he did while he was still with us. —CZ
67. “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
66. “The Climb” (2019)
The premise of “The Climb” has been told so many times it’s a small miracle that this one works at all: Two lifelong buddies test the boundaries of their friendship when a woman comes between them. Yet Michael Covino’s absorbing directorial debut confronts that challenge with stunning cinematic ambition, resulting in a brilliant reinvention of the buddy comedy. Testosterone-fueled dude movies have occupied every facet of the filmmaking landscape in recent years, from the Duplass brothers to “Step Brothers,” but “The Climb” transforms that trope into a fresh vision of boozy showdowns and awkward laments, resulting in a winning tragicomic vision of its own design. —EK
65. “Klown” (2010)
Drafthouse Films/Courtesy Everett Collection
There may be better raunchy sex comedies, and there may be better parenting comedies, but no film in recent memory combines the two as well as “Klown.” The Danish blockbuster tells the story of an utter doofus who, upon learning that his girlfriend is pregnant, takes a 12-year-old boy on a very adult “boys trip” in a ham-fisted attempt to convince his girlfriend (and himself) that he is capable of being a father. Mikkel Nørgaard extracts a million funny scenarios from that simple premise, with plenty of help from his excellent stars Frank Hvam and Casper Christensen, resulting in some of the best cringe comedy produced on either side of the Atlantic this century. —CZ
64. “Bachelorette” (2012)
Leslye Headland’s often abrasive comedy about a bachelorette party of high-school best friends gone riotously awry has a lot of things going for it — but its MVP is Kirsten Dunst as an uptight careerist who unravels over a night of binge-drinking, cocaine-snorting, and a pileup of degrading hijinks that start with a blood stain on a wedding dress. The bride, played by Rebel Wilson, is in over her head rallying her best friends played by Dunst, chainsmoking, drug-doing rebel Lizzy Caplan, and “ditzy” Isla Fisher completely blitzed out of her mind. Taking course over one dark night of heavily intoxicated lost souls, the unhinged and fearless “Bachelorette” is adapted from Headland’s own play, and nearly a decade later, it’s ripe for cult movie status even if it got an unfairly short shrift back in 2012. —RL
63. “The 40-Year-Old Version”
Radha Blank won the Directing Award in the U.S. Dramatic section of Sundance 2020 and no wonder: here was a comedy shot in black-and-white that expressed something vividly, vibrantly new. Blank stars as a version of herself who’s a playwright, but hasn’t had one of her plays produced in a very long time. She’s maybe cherishing that 30 Under 30 award a little too much, the further she gets from having received it. “I just want to be an artist!” she sobs at one point. Yet that’s hard to do when she’s under pressure to write “a Harriet Tubman musical” — something Blank’s been asked to do in real life — and told by one middle aged white male producer that her work is “inauthentic… I asked myself, did a Black person write this?” So Radha ends up cutting a rap mixtape under the name Radhamus Prime, and finds a new creative release. Blank delivered one of the definitive “laugh, or otherwise you’ll cry” comedies of the 21st century. —CB
62. “Sorry to Bother You” (2018)
Potentially the strangest comedy on this list, Boots Riley’s directorial debut “Sorry to Bother You” is, in its director’s words, an “absurdist dark comedy with aspects of magical realism and science fiction inspired by the world of telemarketing.” And yet, that really only scratches the surface of what this movie’s about. Filled with an incredibly talented cast led by Lakeith Stanfield and Tessa Thompson, the film centers around Stanfield’s Cash, a young black telemarketer who adopts a white accent to succeed at his job. This is before the film becomes a parable of corporate greed, a biting commentary on income inequality and modern-day slavery, and a wild absurdist romp along the boulevard of genetic manipulation.
In the end, however, what makes this film so special is Riley’s uniquely singular vision: It’s no exaggeration to state that there is no other movie quite like “Sorry to Bother You.” And a huge trigger warning for potential first-time viewers: Armie Hammer is in this film. But also, knowing what we know now, he is perfectly cast in this film. —LAG
61. “Borat Subsequent Moviefilm” (2020)
©Amazon/Courtesy Everett Collection
Sasha Baron Cohen moved away from “myyyy wifeee” and instead took on the 2020 presidential election to reflect back to viewers what America is like nowadays. “Borat 2” (or “Borat Subsequent Moviefilm”) is full of political stunts, pranks, and celebrity interviews, namely one oft-debated scene involving Rudy Giuliani. This time, Borat (Cohen) is accompanied by his 15-year-old daughter Tutar (an Oscar-nominated Maria Bakalova), whom he is planning on selling as a child bride to Vice President Mike Pence. The absurdities only take off from there, as Tutar travels in a metal cage and visits a pro-life clinic. Fact meets fiction as Borat crashes Pence’s CPAC speech and Tutar interviews Giuliani. The cringe comes only after the laughs, as we realize the joke inevitably is on us all. —SB