Making a good comedy film is hard. You not only have to make them laugh, you have to make them care enough about the characters they’re watching to stick with it for 90-120 minutes. Veer too far into the jokes and you’re left with paper-thin characters. Forget the jokes, and you’ve got yourself a melodrama. But comedy is always evolving, and throughout the 21st century thus far we’ve seen numerous different phases for the genre. No doubt Judd Apatow had a tremendous impact on not only what kinds of comedies audiences respond to, but how comedy films are made—allowing lots of improvisation led to a looseness in a lot of feature films that, frankly, wasn’t there that much before.
But we’ve also seen plenty of other comedic voices arise or return, offering refreshing, unique stories that elevate what could simply be an enjoyable-enough joke-fest to a genuinely great cinematic experience. Folks like Edgar Wright, Shane Black, Phil Lord & Chris Miller, and plenty others carved out very specific voices that spoke to vast audiences, proving you don’t always have to play to the lowest common denominator.
As a result, the past 20 years have been a gold mine for terrific, lasting, and yes hilarious comedy feature films. So we here at Collider wanted to look back and single out the best of the best. Below, our list of the best comedies of the 21st century. So far…
Best in Show (2000)
This was a tough one because A Mighty Wind is also pretty great, but in terms of which is funnier, the award goes to Best in Show. It has the excellent cast of characters with every single actor knocking it out of the park combined with the high-stakes/low-stakes platform of a dog show where the stars may be the pets, but it’s the owners who are the colorful misfits. It’s a movie that’s endearing, heartwarming, biting when need be (Parker Posey and Michael Hitchock are wonderfully loathsome as a bickering couple), and the joke with the “two left feet” is an all-timer. – Matt Goldberg
Wet Hot American Summer (2001)
Wet Hot American Summer is an insane movie. Absurdist comedy is certainly not for everyone, and the film was a box office bomb upon release, but those that were able to find Wet Hot and get on its level discovered a treasure trove of comedy gold. The brainchild of The State alums David Wain and Michael Showalter, the film takes place over a single day at a summer camp in the 1980s, chronicling relatable issues like long-held crushes, pranks, and the impending crash of a massive space satellite that could end life on Earth as we know it. The whole thing is ridiculous, and yet thanks to brilliant casting and a deft approach to navigating the tone, Wet Hot American Summer stands as one of the funniest films ever made. – Adam Chitwood
Bubba Ho-Tep (2002)
Don Coscarelli’s movies always have some offbeat humor packed in, but Bubba Ho-Tep is without a doubt his most outright hilarious movie yet. Based on a short story from prolific genre author Joe Lansdale, Bubba Ho-Tep stars Bruce Campbell and Ossie Davis as two men trapped in a retirement home with a soul-sucking mummy walking the halls and stealing the last days from the elderly. The twist? These old fellas believe they are Elvis Presley and John F. Kennedy, respectively, which gives their undignified battle against the ravishes of old age an absurdist slant — not to mention their fantastical fight against an undead assailant. Bubba Ho-Tep is fearlessly ridiculous, silly, and sometimes breathlessly funny, but it’s also a damn fine horror adventure that’s got heart and guts where it counts. — Haleigh Foutch
School of Rock (2003)
Jack Black had been making his way as a solid comic relief character actor to this point, but Richard Linklater’s script for School of Rock really gave Black a chance to make full use of all of his talents, weaving together his schlubby underdog with his inherently lovable demeanor. And yet it’s Black’s musical ability that’s the film’s ace in the hole since we always buy his character’s musical knowledge and passion. Other films have tried to recapture the special alchemy of Black’s performance to various degrees of success, but he’s at the top of his game in this funny, heartwarming movie. – Matt Goldberg
Anchorman: The Legend of Ron Burgundy (2004)
There may not be a more quotable comedy so far this century. I still can’t look at milk without thinking, “Milk was a bad choice.” Anchorman: The Legend of Ron Burgundy is delightfully madcap, and yet it still holds together, which is remarkable when you consider that they basically reshot the entire thing and gave it a different plot (the original story, which you can see on the DVD, Wake Up, Ron Burgundy!, involved a group of bank robbers). Will Ferrell has done his fair share of great characters, but the arrogant, stupid, misogynistic, yet oddly lovable Ron Burgundy will probably be remembered as his best. It’s a film packed with so many great jokes and it only gets better on repeat viewings. – Matt Goldberg
Mean Girls (2004)
Plenty of Saturday Night Live alums try their hands at the feature film world, but successfully navigating that crossover is oftentimes hard. Tina Fey, however, had no problems whatsoever when she decided to write Mean Girls, based on the self-help book Queen Bees & Wannabes. Fey approaches the material with tact, humor, and insight, crafting a now-classic comedy about what it’s like to navigate the social hellscape known as high school. It’s wildly memorable and hilarious, but also surprising. The film doesn’t take a traditional narrative track, offering twists and turns that put a fresh spin on well-worn territory. Nabbing Freaky Friday filmmaker Mark Waters to direct was a stroke of genius, as the material is treated seriously but not too seriously, and Fey’s dialogue cracks with wit to spare as the talented ensemble fills their roles perfectly. While details may have evolved in the near-decade-and-a-half since the movie was released (!), its truths still sting—and leave you in stiches. – Adam Chitwood
Shaun of the Dead (2004)
While funny is funny, there’s a pretty diverse set of subgeneres within comedy. Edgar Wright’s breakout film Shaun of the Dead, however, is in a class of its own. The “zomromcom” combines elements of horror, comedy, romance, and bromance to result in a perfect cocktail of a movie. I wouldn’t even necessary classify it in one genre—it’s just a great film, full-stop. But it is incredibly funny thanks to Simon Pegg and Nick Frost’s brilliant performances, an airtight script by Pegg and Wright, and last but definitely not least, Wright’s cinematic style. While a lot of comedy filmmakers simply point the camera at funny people and let them do the work, Wright takes advantage of finding a joke anywhere he can, be it in a transition, a hard cut, or the way in which a scene is framed. It elevates the material to a true piece of classic cinema, and if you take the same script and cast but remove Wright as the filmmaker, you lose a tremendous amount of what makes Shaun of the Dead so special in the first place. – Adam Chitwood
Team America: World Police (2004)
Writers/directors Trey Parker and Matt Stone say they instantly regretted their decision to make Team America: World Police once they saw the puppets in motion, but thank God they finished it out. While the South Park creators haven’t dabbled too much in things outside the realm of their Comedy Central series, when they do they tend to strike gold. Team America hilariously skewers post-9/11 panic and The Bush Doctrine, as well as liberal response to the George W. Bush presidency. It does all of this without coming off as (too) preachy, and first and foremost, is downright hilarious. The deadly serious tone of the action heroes makes their buffoonery that much funnier, and the decision to model the film’s structure off Michael Bay action movies was ::chef’s kiss::. – Adam Chitwood
Kiss Kiss, Bang Bang (2005)
It’s almost like someone said, “You can’t have comedy in a noir,” and Shane Black said, “Challenge accepted.” The plot of Kiss Kiss, Bang Bang has all the trappings of a hard-boiled noir, but Black imbues everything with razor-sharp comedy expertly delivered by Robert Downey Jr. and Val Kilmer giving a couple of the best performances of their careers. It’s the kind of film that could be only be made by someone who knows the rules of screenwriting so well that he perfectly knows how to break them. The narration and structure are playful, knowing, but never self-satisfied or smug. Black wasn’t a newcomer to Hollywood when he made this film, but it’s still a shockingly self-assured directorial debut that feels like it only could have come from his mind. – Matt Goldberg
The 40-Year-Old Virgin (2005)
Judd Apatow single-handedly changed the face of comedy for a few years there in the mid-2000s. In the place of high-concept gags or romcoms, The 40-Year-Old Virgin brought a looseness to the genre thanks to Apatow’s willingness to let his cast improvise, but he also aimed to thread James L. Brooks-esque drama into his films. The 40-Year-Old Virgin kicked off this whole trend (which, it should be noted, was also very male-heavy) and it still stands today as an incredibly funny story of a, well, 40-year-old virgin. The casting of Catherine Keener as the love interest was a stroke of genius, and the film also did a great job of reminding the world that Paul Rudd is a hilarious delight. While Apatow’s subsequent features would be commercially successful if a bit of a mixed bag quality-wise, the legacy and impact of The 40-Year-Old Virgin looms large. – Adam Chitwood
Borat (2006)
The “Borat” voice and Sacha Baron Cohen’s shtick have become so familiar at this point that it’s hard to remember that this film hit like a bolt from the blue when it was released. Some people were familiar with the Borat character from The Ali G Show, but no one saw Borat coming and how far Cohen was willing to go for a joke. It’s a movie that’s truly getting away with something in just about every scene, and it’s a comedic marvel not just for the set-ups of the scenes, but also for how Cohen is able to think on his feet without ever breaking character. While we may all have a Borat impression in our back pocket, this film has never been truly replicated, even by Cohen himself. – Matt Goldberg
Idiocracy (2006)
Filmmaker Mike Judge’s Idiocracy was intended to be a satire, crafted in the midst of the Bush Administration as a hilarious, far-fetched sci-fi tale about where humanity could be going. As it turns out, Judge was depressingly way too on the mark. Watching Idiocracy now is like going through the looking glass, peering into an all-too-familiar future that seems far closer than it’s supposed to be. From President Camacho to the public’s eagerness to be as dumb as possible, Idiocracy is a biting satire about the American citizenry at its worst, and, possibly, at its most candid. It’s still funny, but hoo-boy this is a tough one to watch these days. – Adam Chitwood
Walk Hard: The Dewey Cox Story (2007)
Walk Hard is an all-time great spoof that savages the music biopic genre so badly that it basically killed anyone trying to play by those rules in the future. While its clear inspirations are contemporaries Walk the Line and Ray, Walk Hard goes beyond by expanding its parody to a history of American music in general. John C. Reilly is amazing (as always) and the songs are as catchy as they are witty parodies of various artists. It’s a film that pokes fun at music and biopics in equal measure and succeeds wildly at both. – Matt Goldberg
Superbad (2007)
Superbad was a stone-cold classic from the first time it hit theaters. Immediately, the film had a timeless quality that was reminiscent of coming-of-age comedies like Ferris Beuller’s Day Off, and a large part of that is due to the care and personal nature of the screenplay by Seth Rogen and Evan Goldberg. Inspired by their own experiences, Superbad is essentially the story of two high school best friends coming to terms with the fact that once they go to college, they may not be best friends anymore. It’s a realization that many face, but in Superbad it’s captured with heart, humor, and lots of dick jokes. Superbad is basically a love story between Jonah Hill and Michael Cera, and that heart that permeates all Judd Apatow productions elevates the material to something truly special. Not to mention the fact that Superbad first introduced audiences to the incomparable Emma Stone. – Adam Chitwood
Hot Fuzz (2007)
While there certainly could have been the temptation to do “Shaun of the Dead with cops” for Hot Fuzz, the trio of Edgar Wright, Simon Pegg, and Nick Frost reunited for something completely different but equally ambitious. The film doesn’t rely on the same tricks that made Shaun of the Dead so great in the first place, and instead allows Wright to show off different skills as a filmmaker as he crafts a bona fide action movie about British cops in a sleepy countryside town. Like Shaun it’s still hilarious, and Wright continues to mine jokes out of cinematic techniques, but the story’s twist adds yet another layer of humor and intrigue, culminating in an action finale the likes of which you’ve never really seen before. – Adam Chitwood
Step Brothers (2008)
Step Brothers is Adam McKay’s masterpiece. While films like Anchorman and Talladega Nights are great, Step Brothers on a whole other level—and I’ll be honest it took a couple viewings for me to come around to this. The commitment to the gag—that Will Ferrell and John C. Reilly play adult men who literally behave like children when their parents get married—is intense, and while there was no doubt plenty of improvisation in the filming of Step Brothers, the final product runs like a swiss watch. The cast is tremendous, the story takes delightfully wild turns, and yet somehow the film is able to hone in on some really relatable aspects of family despite also having a sequence in which Reilly dresses up as a Klansman and Ferrell dresses up as a Nazi in order to deter new home buyers. – Adam Chitwood
In Bruges (2008)
Celebrated playwright Martin McDonagh made his filmmaking debut in 2008 with In Bruges; a prickly, venomous spin on the crime comedy that starts out as pure quick-witted banter between a pair of Irish assassins, played by the always wonderful Brendan Gleeson and Colin Farrell in a career-redefining turn, but the film quickly transforms into something closer to tragedy. Or perhaps more accurately, and fitting for a debut film from a man of the theater, In Bruges is like watching the tragedy and comedy masks merge into a heart-breaking, hilarious, and unusual tale about grief, guilt and redemption, set in the cinematic fairy tale streets of Bruges. As the bullets fly and the bloodshed mounts, McDonagh keeps the zingers coming and even when In Bruges breaks your heart, it somehow leaves you with a crooked smile on your face. — Haleigh Foutch
Forgetting Sarah Marshall (2008)
Romantic comedies count too, obviously, and Forgetting Sarah Marshall stands as one of the best of that subgenre. As Judd Apatow's cohorts started to branch out and write their own material, Jason Segel birthed us this delightful, sincere breakup romp. It's hilarious and heartfelt in equal measure, which makes it special. But it's also wickedly raunchy, as evidenced by Segel's now-famous full frontal breakup scene at the beginning of the movie. It takes a lot of unexpected twists and turns, and while Segel and Nicholas Stoller would further blur the lines between comedy and drama in films like The Five-Year Engagement, this one still stands a cut above thanks to its fairly tight narrative and huge heart. Oh, and Kristen Bell is lowkey the film's MVP. — Adam Chitwood
Cloudy with a Chance of Meatballs (2009)
How do you take a thin children’s book and turn it into an inspired disaster comedy? Look no further than Cloudy with a Chance of Meatballs, which is far better than it has any right to be. It’s unabashedly weird and sometimes downright disturbing (I have no idea how they got away with the snowball scene), but it’s always wonderful with so much heart at the center of its unrelentingly goofy comedy. This film makes the list for a variety of reasons, but we’d probably have to include it because it’s the only movie in history with a Welcome to Mooseport joke, and that includes Welcome to Mooseport. – Matt Goldberg
The Informant! (2009)
Steven Soderbergh has lowkey been making great comedies for well over a decade now, but The Informant! is one that can 100% be classified as such. Soderbergh and writer Scott Z. Burns took what other filmmakers might turn into an Erin Brockovich-esque drama and made a true story farce. Matt Damon is next-level as Mark Whitacre, a whistle-blower who is far more stupid than he thinks he is. The film features quite possibly the best narration in cinema history, as Whitacre’s actions are juxtaposed with his odd, meandering, hilarious thoughts that oftentimes directly contradict what he’s doing. It’s gorgeously shot, impeccably crafted, and a blast from start to finish. The Informant! is proof positive that Steven Soderbergh is one of the funniest filmmakers working today. – Adam Chitwood