July 4, 2020

The 35 Best Comedies of the 21st Century, Ranked

Now more than ever, the world could use a laugh. This bizarre, in-progress century has already produced any number of great comedies, which is to say that many of your (and our) favorites were left out: sorry, “Toy Story 3”; sorry, “Knocked Up.” As we tend to lean toward the indie side — and away from certain men-behaving-badly movies — there are also some titles on here that you might not have seen.

There are even some you may not consider to be straightforward comedies. You may not think of “Lost in Translation” or “Mistress America” as laugh riots, but we felt it best to be broad in our approach — any movie that balances its darker shades with cathartic humor was eligible. You’ll notice that we like women and Working Title (the British production company responsible for several titles on this list), which is to say: This is less a definitive statement and more a jumping-off point, so feel free to chime in.

UPDATE: Since this list was published in 2017, many funny movies have been released. We have updated the list with additional entries from the past three years, curated by Anne Thompson, with additional contributions from members of the IndieWire staff. However, our original ranking, available below, still stands.

“The Big Sick” (2017)

Emily Gordon and Kumail Nanjiani nabbed a Best Original Screenplay nomination for synthesizing their harrowing true romance into a sharp and winsome comedy about a courtship that begins with a culture clash and survives a coma. After Gordon and Nanjiani wrote the script as an intense form of couples therapy, uber-producer Judd Apatow and director Michael Showalter whipped it into shape and cast Zoe Kazan as the young woman who falls for a Pakistani-American comic and Uber driver (Nanjiani). When she’s hospitalized, her parents (Holly Hunter and Ray Romano) learn to appreciate her tortured lover’s affection for their sleeping beauty before she comes back to life. —AT

“Booksmart” (2019)

The best possible modern mashup of “Superbad” and “Bridesmaids” and innumerable other comedies about the glory and grossness of close friendship, Olivia Wilde’s feature directorial debut isn’t just an ode to smart girls, bad high school experiences, and one last night of debauchery, it’s also just damn funny. Initially inspired by a decade-old Black List script (which leaned a bit more heavily into the romantic possibilities of a couple of overachievers going nuts during the waning days of high school), screenwriter Katie Silberman’s take on the material puts a fresh twist on a classic setup. Best friends forever, Molly (Beanie Feldstein) and Amy (Kaitlyn Dever) have spent their high school years hitting the books and shrugging off any and all social gatherings (aside, of course, from sleepovers with each other and the necessary political protest), all in hopes of putting all their energies towards getting top grades. It’s all panned out as they planned.

But they discover that, well, it’s also panned out for everyone else who didn’t hole themselves up for four years. Cue a “one last night to do something cool” and “big important party” arc, which lovingly follows the dynamic duo as they attempt to make up for lost time. The contemporary touches help bolster an already deeply felt and very amusing film about two good girls trying to do bad (Amy is a lesbian, their high school is believably diverse, the teens are treated like actual humans). Meanwhile, Feldstein and Dever’s bond (which exists off-screen as well) raises the emotion and humor of the film at every turn. Sharply directed, snappily edited, and aided by a banger of a soundtrack, it’s a high school classic in the making. —Kate Erbland

“Crazy Rich Asians” (2018)

Sanja Bucko

Based on Kevin Kwan’s bestselling novel of the same name, “Crazy Rich Asians” follows Chinese-American professor Rachel Chu (Constance Wu) as she travels to Singapore with her secretly wealthy boyfriend Nick Young (Henry Golding). Once the pair arrive in the glittering country, Rachel is shocked to learn just how rich Nick and his family are (really, really rich), and how fiercely his mother Eleanor (Michelle Yeoh) wants to protect her son from marrying seemingly below his station. Despite the glitzy nature of the story — and its unabashed rom-com sensibilities — the film takes great pains to provide empathetic emotion to each character, even the seeming bad guys. That might not sound like obvious comedic material, but it’s exactly that sort of gamble that allowed Jon M. Chu’s smash hit to earn its laughs: nothing in the film is cheap, including the humor.

Even its more broad gags, including the exploits of the new money Goh family (led by Ken Jeong, but absolutely dominated by Awkwafina in a show-stealing turn as Rachel’s old pal Peik) and the vicious, Godfather-inspired pranks from Nick’s group of catty girlfriends, are steeped in careful character work, all the better to make those laughs really stick. Nothing may be more obviously funny than Peik popping her trunk outside the Young estate to get a better look at the wide variety of dressy options she stashes there for just such an occasion, but the hilarity comes straight from the heart. —KE

“Girls Trip” (2017)

Michele K Short/Universal/Kobal/Shutterstock

There’s plenty of star power behind “Girls Trip,” including always-bankable director Malcolm D. Lee and big names like Queen Latifah and Jada Pinkett Smith, but it’s impossible to deny its biggest breakout: then-newcomer Tiffany Haddish, who made off with not only the comedy’s best lines and bits of physical humor, but its most eye-popping performance. Haddish’s zippy charisma sets the film’s tone early, zinging between bouts of physical comedy (no one lunges at a co-star with as much pizzazz as Haddish) and wonderful off-color one-liners that are as shocking as they are masterfully delivered. Later in the film, Haddish serves up what will likely become contemporary cinema’s best example of how to use fruit to simulate sex acts (sorry, “American Pie”), a sequence so deliciously raunchy that it’s worth the price of admission alone.

Those pure laughs are more than enough to sustain a comedy so crystalline that it was a classic the minute it hit screens, as “Girls Trip” nails laugh after laugh even amidst — and oftentimes because of — dramatic issues that wouldn’t be out of place in a Lifetime movie. As the film’s central ladies make their way through all the glory that New Orleans’ Essence Fest has to offer, including run-ins with a slew of big talents in a seemingly never-ending parade of cameos (Diddy makes off with the best one, predictably bolstered by Haddish’s involvement) and at least one wildly ill-conceived adventure fueled by absinthe, “Girls Trip” keeps the momentum whirling ever onward into the next big comedic set piece. Even as it all ends with a heartwarming reveal, that doesn’t dilute its more raucous sensibilities; it only makes it more clear why Lee and his ladies should turn “Girls Trip” into a franchise that can spawn more uproarious vacations. —KE

“Lady Bird” (2017)

A24

Greta Gerwig’s feature directing debut earned Oscar nominations for her writing and directing, and Irish actress Saoirse Ronan scored her third Oscar nod as Christine “Lady Bird” Macpherson, a culture-vulture eager to escape her Sacramento Catholic School. When scouting local colleges, her frustrated mother (Laurie Metcalf) drives the teenager so crazy she jumps out of the moving car. Tracy Letts is Lady Bird’s sad and adoring father, while Lucas Hedges and Timothee Chalamet are her challenging romantic entanglements.

It’s the best mother-daughter relationship comedy since “Terms of Endearment,” but the emotional depth that drives the movie forward is never too far away from a well-earned laugh. Gerwig’s sense of comic timing is impeccable, from the memorable car-jumping sequence of its opening moments all the way through the rousing finale. —AT

“Thor: Ragnarok” (2017)

Disney/Marvel

“Thor” proved the most challenging superhero to get right for Disney and Marvel Studios. After Kenneth Branagh successfully launched the franchise in 2011 by rooting it in Shakespearean family drama, Alan Taylor derailed the comic book hero with his flimsy 2013 sequel “The Dark World.” Fortunately, the studios brought in Taika Waititi to helm “Thor: Ragnarok” and that decision led to one of the best Marvel movies to date.

Brimming with eye-popping colors and the sharp humor that defines all of Waititi’s movies, “Thor: Ragnarok” is light on its feet and allows Hemsworth not to be overburdened with the world-ending pseudo-gravitas of “The Dark World.” “Ragnarok” takes Thor out of Asgard and makes him a prisoner on Sakaar, but Waititi doesn’t just repeat the fish-out-of-water story of the original “Thor.” The writer-director makes the smart decision to pair Thor’s Hemworth opposite Mark Ruffalo’s Bruce Banner/Hulk in order to create the comic book equivalent of a rollicking buddy comedy. Throw in Tessa Thompson’s Valkyrie and you get a superhero movie built on the comedic chemistry that sizzles among its cast members. —Zack Sharf

“The Death of Stalin” (2017)

Armondo Ianucci’s first adapted work takes the vulgar bureaucratic satire of “Veep” and “In the Loop” into the Soviet Union, with all the delightful and nasty twists you can imagine. Adapting a scenario by Fabien Nury and Thierry Robin’s graphic novel, the movie unfolds against the tumultuous backdrop of 1953 as Stalin’s sudden demise creates a ridiculous power struggle among the awful, vindictive politicians left to sort out the government he left behind (and also the persecution). Steve Buscemi leads an extraordinary cast of (non-accented) actors who relish the opportunity to toss around Ianucci’s combative dialogue and vulgar outbursts in a delightful self-destructive spiral.

Yet Ianucci never sugarcoats the nature of the villains he takes on as his protagonists; if anything, the bleak finale provides a cogent reminder that even the nuttiest leaders are more than just punchlines when real lives are at stake. Still, while the movie contains remarkable period detail, “The Death of Stalin” has more in common with the Marx brothers than anything about the period in which it’s set: It’s “Duck Soup” with dictators. —Eric Kohn

“Knives Out” (2019)

The devious and crackling “Knives Out” might typically be considered as more of a whodunnit than a comedy, but a time when even the most star-studded comedies have to be disguised as something else in order to be released in theaters, there’s no denying that Rian Johnson’s mega-hit is one of the funniest murder-mysteries ever made. That starts with Daniel Craig’s Benoit Blanc, a Southern-Fried super detective who chews every last inch of the film’s richly appointed scenery as if it were bad manners to leave any of it on his plate.

And while there’s only room for one monologue about donut holes in this movie, the rest of Johnson’s ensemble cast each gets their moments to shine. Cheekily pivoting from “America’s Ass” to “America’s Asshole,” Chris Evans is a shit-eating delight as the entitled son of murdered novelist Harlan Thrombey, Toni Collette is the first genuinely funny Instagram influencer in the entire history of creative fiction, and Michael Shannon is there to prove that some reaction shots can land harder than any punchline. But it’s Harlan Thrombey’s unassuming caregiver Marta (played by Ana de Armas) who gets — and gives — the last laugh. The only character who fully recognizes that she’s in a farce about rich Americans who think of their wealth as a birthright, Marta delivers the best joke of this unexpectedly hilarious movie by reducing the Thrombey family to a killer punchline. —David Ehrlich

“Once Upon a Time in Hollywood” (2019)

Sony

Quentin Tarantino’s $90-million elegy to a lost Hollywood is hilarious — until it’s not. The shifting 1969 narrative centers on declining western TV star Rick Dalton (Leonardo DiCaprio) and his loyal stunt double and driver Cliff Booth (Brad Pitt). Dalton lives on Cielo Drive, next door to angelic rising star Sharon Tate (Margot Robbie) and her A-list director Roman Polanski (Rafal Zawierucha), hot off “Rosemary’s Baby.” They’re riding the counterculture surge in Hollywood, while Dalton swigs booze in his trailer and loses his shit when he forgets his lines. Pitt won the Supporting Actor Oscar as war hero Booth, who is more zen, and more dangerous than his boss, holding his own both with Bruce Lee (Mike Moh) and the menacing followers of Charles Manson. Tarantino often doesn’t get enough credit for his comedic chops, but “Hollywood” proves that he excels at finding ways to make you laugh when you least expect It. — AT

“Parasite” (2019)

Neon

The momentum toward the Best Picture Oscar had been building steadily since the Cannes Palme d’Or win for Hitchcockian genre-master Bong Joon Ho (“Okja” and “Snowpiercer”). This raucously entertaining comedy — and yes, it’s a very dark comedy — about a family of con artists who infiltrate a rich family far above them in status was a surprisingly accessible thrill-ride. “Parasite” excels at telling us who we are, in every society all over the world.

As unlikable as many of the film’s characters are, you still root for them, partly because they make you laugh. The bloody finale teeters on the edge on slapstick, like many of the film’s big moments, but every punchline arrives like a shock to the system. In truth, “Parasite” is an unclassifiable blend: Director Bong’s mix of comedy, thriller, and social critique wowed global audiences, boosted by enthusiastic independent distributors who pushed the film into a global hit ($201 million foreign, $53 million domestic). That success proves there is true hope for filmmakers looking to entertain the masses on their own terms. — AT

25. “Harold and Kumar Go to White Castle” (2004)

How far would you go for some sliders? In “Harold and Kumar,” a couple of stoners getting the munchies is treated as an odyssey of epic (and hilarious) proportions. The unlikely franchise-starter has endeared itself to cannabis enthusiasts as well as those who don’t partake, inspiring moviegoers to Just Say Yes for more than a decade; given the strides that marijuana (both medicinal and otherwise) has made in recent years, you could even say that the cult classic was ahead of the curve. –MN

24. “Juno” (2007)

The chemical equation of writer Diablo Cody plus director Jason Reitman explodes onscreen with this non-traditional family comedy showcasing Cody’s edgy contemporary dialogue. The story of a whip-smart teenager (Ellen Page) who gets pregnant by her new boyfriend (Michael Cera) and decides to give the baby up for adoption to a yuppie couple (Jennifer Garner and Jason Bateman) plays like a comedy but packs an unexpected emotional wallop. Everyone came out ahead on this movie (Cody won the Best Original Screenplay Oscar), which grossed $231 million worldwide. The down side: this inventive indie spawned far too many imitators.  —AT

23. “Shaun of the Dead” (2004)

This acerbic action comedy introduced a winning combo: sparring buddies Simon Pegg and Nick Frost and master of style Edgar Wright, who dreamed up the script with Pegg. He plays a sad sack who turns out to be more brave and adept at slaying the walking dead than he ever would have thought. And he gets the girl. More Working Title collaborations followed, but the first time out was the charm: mash up a witty British romance and a zombie gorefest, and hilarity ensues. —AT

22. “Old School” (2003)

You’re my boy, Blue! Say what you will about the Frat Pack films that followed it, but “Old School” still gets a passing grade. Part of the one-two punch (the other being “Elf”) that made Will Ferrell a bona fide movie star, this reminder that you’re never too old to start a fraternity also brought us Luke Wilson and Vince Vaughn at their best. Its hilarity is all the more impressive when considering other movies of its kind haven’t aged as well — we’re looking at you, “Wedding Crashers.” —MN

21. “Trainwreck” (2015)

Producer Judd Apatow steered breakout standup comic Amy Schumer to her smash big-screen debut ($141 million worldwide) by helping her to write a recognizably real woman to play — accessible, honest, emotional — within the genre confines of a mainstream romantic comedy. Sure, potty-mouth Schumer acts out, surrounded by crazy chaos, but leading man Bill Hader makes a gallant, alert, reactive foil, and at the end, order is restored and Schumer gets her man. Even so, “Trainwreck” moves the needle when it comes to male-female relations at the movies, bloody tampons and all. —AT

20. “O Brother, Where Art Thou?” (2000)

Packed with corn-pone humor and catchy southern roots music, this rollicking Coen brothers 1930s adaptation of Homer’s “The Odyssey” follows a gang of escaped dimwit prisoners led by pomaded charmer Everett McGill (George Clooney), who tries to get back his wife (“Raising Arizona” star Holly Hunter) by singing her into submission. T-Bone Burnett’s best-selling soundtrack won the Grammy for album of the year and cinematographer Roger Deakins nabbed an Oscar nomination for his pioneering digital alterations to this Working Title film’s color palette. But as always, helping Clooney, Hunter, Tim Blake Nelson, John Turturro and John Goodman earn this meandering fable’s countless laughs was the main goal.  —AT

19. “Best in Show” (2000)

It doesn’t go up to 11, but Christopher Guest’s account of a barking-mad dog show is still the finest mockumentary ever made about anything besides a Stonehenge-obsessed rock band. Last year’s similar “Mascots” was funny enough, but mostly served to remind viewers what a one-of-a-kind accomplishment “Best in Show” is — the line between laughing with and at these characters may be thin as Guest endears his ensemble to us even as he mocks them, but at least we never stop rooting for the doggos. 12/10 would watch. —MN

18. “About a Boy” (2002)

Do we miss Hugh Grant yet? The once-ubiquitous rom-com star has grown choosier in recent years, appearing onscreen less often so that he might command more attention when he does. His smug charm has rarely been but to better use than it was in “About a Boy” (yes, Working Title), which came during that happy early-2000s period when adaptations of Nick Hornby novels were a genre unto themselves. No man is an island, which is to say that Nicholas Hoult, Toni Collette and Rachel Weisz deserve as much credit as Grant. —MN

17. “Borat” (2006)

If “Bruno” and “The Dictator” taught us anything, it’s that “Borat” was truly lightning in a bottle. Sacha Baron Cohen’s feature-length social experiment pissed off nearly as many people as it delighted, which surely pleased the fearless provocateur (even if Pamela Anderson seemed pretty bewildered by the whole experience). Plus, when’s the last time a comedy was credited with bringing back a comeback as hilariously lame as “…not!”, let alone increasing tourism to Kazakhstan? —MN

16. “The Heat” (2013)

This yin-and-yang teaming of Sandra Bullock and Melissa McCarthy as mismatched cops in a summer buddy comedy was Paul Feig’s wildly successful ($230 million) follow-up to “Bridesmaids.” Bullock’s ambitious, uptight and trim FBI agent is forced to team with McCarthy’s sloppy, overweight, profane, maverick Boston cop in order to nab a nasty drug lord. Feig’s casting combo was inspired, as McCarthy’s anarchic improv loosens up Bullock’s controlled comic timing. —AT

Check out choices 15 – 11 on the next page, including bad neighbors, obvious children, and unexpected sisters.

Source: IndieWire film