It’s difficult to make an excellent comedy movie. Besides making them laugh, you need to make them care enough about the characters they’re watching to keep them engaged for 90-120 minutes. If you stray too deep into the humor, you’ll be left with characters who are as thin as paper. You’ve got a melodrama if you forget the humor. However, humor is a dynamic genre that has gone through various phases in the twenty-first century. With his openness to improvisation and his willingness to experiment, Judd Apatow changed not only what kind of comedies were popular but also the process by which they were made. This led to a looseness in many feature films that wasn’t before present.
Many more humorous voices have also emerged or returned, giving fresh and original storylines that transcend what could be an enjoyable-enough joke-fest into a true wonderful cinematic experience. You don’t always have to play to the lowest common denominator, as demonstrated by Edgar Wright, Shane Black, Phil Lord & Chris Miller, and many more.
A result of this is a treasure trove of great, long-lasting comedic feature films during the previous 20 years. That’s why at Collider we’ve decided to take a look back and select some of our favorites. The following is a list of the finest comedies of the 21st century, as voted on by critics. This is what we know thus far…
1. Best in Show (2000)
A Mighty Wind is also quite good, so choosing between the two was difficult. However, the award goes to Best in Show for its superior sense of humor. An terrific cast of characters and a dog show platform where the stars are the pets but the owners are the colorful misfit characters make this a show that’s hard to put down. When Parker Posey and Michael Hitchcock are arguing, they’re hilariously awful. The “two left feet” joke is a classic. It’s Matt Goldberg!
2. Wet Hot American Summer (2001)
What a wacky film, Wet Hot American Summer. Even though Wet Hot was a box office failure when it was released, the audience that was able to find the picture and get on board with its absurdist humor was rewarded with an abundance of laughs. Relatable themes like long-term relationships, the pranking and approaching destruction of a gigantic space satellite are all dealt with by The State alumni David Wain and Michael Showalter in the film, which takes place over one day at the camp of a 1980s summer camp. Everything about Wet Hot American Summer is ludicrous, yet that doesn’t stop it from being among the funniest movies ever made, thanks to great casting and a masterful handling of the tone. In other words, Adam Chitwood
3. Bubba Ho-Tep (2002)
This is Don Coscarelli’s most blatantly hilarious film to date, and he’s always been known for his unusual humor. It stars Bruce Campbell and Ossie Davis as two men locked in a retirement home with a soul-sucking Mummy who walks the halls and steals the last days from those who are too old to fight back. What’s the big deal here? Elvis Presley and John F. Kennedy are two elderly men who believe they’re the real deal, and their absurdist battle against the ravages of old age and an undead assailant adds to the absurdity of the situation. Bubba Ho-Tep is plenty of hilarity, but it’s also a solid horror film with plenty of guts and a strong sense of dread. Haleigh Foutch —
4. School of Rock (2003)
Prior to his role in School of Rock, Jack Black had established himself as a reliable comedic relief actor, but Richard Linklater’s writing provided Black the chance to employ all of his skills, combining his portrayal of the chubby underdog with his endearing personality. And yet, we always buy Black’s character’s expertise and passion for music, making his musical ability the film’s ace in the hole. Other filmmakers have tried their best to replicate the magic of Black’s performance, but this is the best performance he’s ever given. It’s Matt Goldberg!
5. Anchorman: The Legend of Ron Burgundy (2004)
So far this century, there may not be a more quotable comedy. Even now, when I see milk, I can’t help but think, “Milk was a poor choice.” When you consider that they essentially reshot the entire movie and gave it a different plot (the previous story, which can be seen on the DVD, Wake Up, Ron Burgundy!, had a crew of bank robbers), it’s astonishing that Anchorman: The Legend of Ron Burgundy still hangs together. The arrogant, dumb, misogynistic, yet weirdly charming Ron Burgundy is likely to be Will Ferrell’s most memorable character. It’s a film jam-packed with hilarious humor that gets even funnier with each subsequent viewing. It’s Matt Goldberg!
6. Mean Girls (2004)
Many SNL alums attempt their hand at the feature film realm, but it is sometimes difficult to navigate that transition successfully. Tina Fey, on the other hand, had no issues when she decided to create Mean Girls, based on the self-help book Queen Bees and Wannabes. For Fey, this material is approached with a mixture of humor and wisdom, creating a now-classic comedy about navigating the social hellscape known as high school.” It’s humorous and unforgettable, but it’s also a bit of a surprise. To put it another way, instead of following a conventional plot line, the film takes unexpected detours. Mark Waters, the director of Freaky Friday, was the perfect choice for this picture since the subject is treated with respect but not too much respect, and Fey’s language cracks with wit to spare. The movie’s realities still sting and leave you in stitches, even though the facts may have changed in the nearly decade-and-a-half after its debut (!). In other words, Adam Chitwood
7. Shaun of the Dead (2004)
Comedy has a wide range of subgenres, so it’s important to know what you’re getting yourself into. In contrast, Edgar Wright’s debut picture Shaun of the Dead is in a league of its own. A “zomromcom” is a film that blends aspects of horror, comedy, love, and bromance. To me, it doesn’t matter what genre it belongs to—it is simply a fantastic film. But it’s hilarious because to Simon Pegg and Nick Frost’s superb performances, Pegg and Wright’s tight script, and Wright’s cinematic aesthetic, to name just a few things. Wright, in contrast to many other comedic filmmakers, isn’t afraid to look for jokes in unexpected places, whether it’s in a transition, a harsh cut, or the way a scene is structured. You lose a lot of what makes the film so special if you take the same script and cast and remove Wright as the director. In other words, Adam Chitwood
8. Team America: World Police (2004)
Filmmakers Trey Parker and Matt Stone claim they immediately regretted doing Team America: World Police following their first encounter with the puppets in action, but they are grateful they were able to see it through. While the South Park creators haven’t strayed too far from their Comedy Central show, they’ve found success when they did. The Bush Doctrine, post-9/11 fear, and the liberal response to George W. Bush’s presidency are all lampooned by Team America. As a bonus, it’s also a lot of fun to watch. To make their buffoonery even hilarious, the action heroes have a dead serious tone and the film’s structure is based on Michael Bay action blockbusters. In other words, Adam Chitwood
9. Kiss Kiss, Bang Bang (2005)
I think Shane Black’s response to someone saying, “You can’t have comedy in a noir,” was “Challenge accepted.” Robert Downey Jr. and Val Kilmer provide two of the best performances of their lives in Kiss Kiss, Bang Bang’s narrative, which has all the trappings of a hard-boiled noir, but Black infuses everything with razor-sharp humour. Someone who understands the norms of screenwriting so well that he knows just how to break them can only make this kind of picture. There is nothing self-satisfied or pompous about the storytelling and organization. It’s hard to believe that this was Black’s directorial debut, even though he was already a seasoned Hollywood veteran when he made it. It’s Matt Goldberg!
10. The 40-Year-Old Virgin (2005)
In the mid-2000s, Judd Apatow single-handedly reshaped the landscape of comedy. Apatow’s willingness to let his cast improvise in The 40-Year-Old Virgin helped relax the genre, but he also intended to weave James L. Brooks-style drama into his films, instead of high-concept comedies or romcoms. A hilarious story about a 40-year-old virgin, The 40-Year-Old Virgin sparked this whole fad (which, it should be added, was also highly male-heavy), and it still exists today. As a result of Catherine Keener’s role as the love interest and Paul Rudd’s funny performance, the picture has been hailed as one of the year’s best comedies. In spite of the fact that Apatow’s subsequent films would be economically successful, the legacy and influence of The 40-Year-Old Virgin will always be there. In other words, Adam Chitwood
11. Borat (2006)
The “Borat” voice and Sacha Baron Cohen’s shtick have become so ingrained in our culture that it’s hard to remember that this film was a surprise when it came out. The Ali G Show’s Borat figure was well-known, but no one sawBoratcoming and the absurdity of Cohen’s joke until it was too late. A comedy marvel, not only for the scene set-ups but also for how Cohen is able to think on his feet without ever losing character, this film actually gets away with something in almost every scene. When it comes to Borat, even Cohen himself hasn’t been able to reproduce the movie’s magic. It’s Matt Goldberg!
12. Idiocracy (2006)
Idiocracy, a film by Mike Judge, was meant to be a satire of the Bush Administration, a far-fetched sci-fi story about the future of humanity. In the end, Judge’s assessment of the situation was tragically accurate. Now that we’ve seen Idiocracy, it’s as if we’ve gone through the looking-glass and seen into a future that appears closer than it should have been. President Camacho and the general public’s eagerness to be as stupid as possible are only two examples of how Idiocracy mocks the American people at their worst and, perhaps, at their most honest. It’s still a lot of fun, but it’s a lot harder to sit through these days. In other words, Adam Chitwood
13. Walk Hard: The Dewey Cox Story (2007)
This is one of the greatest music biopic spoofs of all time, and it savages it so brutally that it effectively wipes off the entire genre of music biopics. Walk the Line and Ray are obvious influences, but Walk Hard takes its parody a step further by exploring the history of popular music in the United States as a whole. As always, John C. Reilly is awe-inspiring and the songs are both catchy and clever parodies of other singers. As a biographical and musical parody, it’s a smashing success on every level. It’s Matt Goldberg!
14. Superbad (2007)
From the moment it was released, Superbad was an instant classic. To a considerable extent, Seth Rogen and Evan Goldberg’s writing contributed to the film’s timeless quality, evocative of Ferris Beuller’s Day Off, a coming-of-age comedy. Superbad is the story of two closest friends in high school coming to terms with the possibility that they would no longer be best friends once they enter college. It’s a common revelation, but in Superbad, it’s portrayed with warmth, levity, and plenty of scatological humor. As with all Judd Apatow films, there’s a lot of heart in Superbad, and it raises the story between Jonah Hill and Michael Cera to something very wonderful. Not to mention that it was in Superbad that the world first met Emma Stone. In other words, Adam Chitwood
15. Hot Fuzz (2007)
For Hot Fuzz, Edgar Wright, Simon Pegg, and Nick Frost reassembled to work on something very different but no less ambitious than “Shaun of the Dead with cops.” Filmmaker Edgar Wright is allowed to show off new skills as a filmmaker as he creates an action movie about British officers in a peaceful rural hamlet. As with Shaun, the tale twist adds still another layer of humor, mystery, and action culminating in an action conclusion like you’ve never truly seen before in a film like this. In other words, Adam Chitwood
16. Step Brothers (2008)
Adam McKay’s masterpiece is Step Brothers. While wonderful films like Anchorman and Talladega Nights exist, Step Brothers is on another level entirely—and I’ll be honest, it took me a few viewings before I really got it. While there was no doubt some improvisation during the filming of Step Brothers, the end product works like a Swiss watch thanks to the actors’ dedication to the humor, which has Will Ferrell and John C. Reilly playing adult men who literally behave like children when their parents get married. In spite of scenes in which Reilly dressed as a Klansman and Ferrell dresses as a Nazi in order to scare away potential home buyers, the film manages to focus on some deeply realistic aspects of family life. In other words, Adam Chitwood
17. In Bruges (2008)
He made his feature debut with In Bruges in 2008, a crime comedy that begins out as a quick-witted banter between a couple of Irish assassins, portrayed by the always brilliant Brendan Gleeson and Colin Farrell in a career-defining turn, but the film soon morphs into something closer to tragedy. It’s more like watching the tragedy and comedy masks mix into a heart-breaking, humorous, and strange story about loss, remorse, and redemption set in the cinematic fairy tale streets of Bruges, which is fitting for a debut film from a man of the stage. It’s hard to look away from In Bruges without a crooked smile on your face, no matter how hard the movie tries to shatter your heart as the gunshots fly and the bloodshed increases. Haleigh Foutch —
18. Forgetting Sarah Marshall (2008)
Of course, romantic comedies like Forgetting Sarah Marshall, which is one of the best in the category, are taken into consideration. Jason Segel, one of Judd Apatow’s collaborators, began to develop his own work as he and his comrades began to venture out and write their own content. It’s both sincere and amusing, which makes it truly unique. Also vulgar, as proven by Segel’s iconic full frontal breakup scene at the beginning. Segel and Stoller would later blur the borders between comedy and drama in films like The Five-Year Engagement, but this one remains a cut above thanks to its tightly wound plot and enormous heart. In addition to that, Kristen Bell is the film’s understated hero. Adam Chitwood –
19. Cloudy with a Chance of Meatballs (2009)
An imaginative disaster comedy can be made out of a thin children’s book. There’s no need to look any further than Cloudy with a Chance of Meatballs, which is considerably superior to what it deserves to be. Unabashedly odd and often scary (I’m not sure how they got away with the snowball scene), but it’s always fantastic thanks to its unrelentingly wacky comedy with a lot of love at its core. A number of factors contribute to its inclusion, but the most compelling argument is that it is the only film in history to contain a joke about the fictional town of “Welcome to Mooseport.” It’s Matt Goldberg!
20. The Informant! (2009)
Soderbergh has been making funny movies for a long time, but The Informant! is his first that can be called a comedy in the strictest sense. What other filmmakers may have turned into an Erin Brockovich-style drama, Soderbergh and writer Scott Z. Burns turned into a true tale farce. Matt Damon’s performance as Mark Whitacre, a naive whistle-blower, is nothing short of brilliant. Even though Whitacre’s deeds are paired with his rambling and often contradictory beliefs, the film’s narration is arguably the best in cinematic history. From beginning to end, it’s an absolute joy to watch. This latest film by Steven Soderbergh proves that he is one of the funniest directors in the business.