While the comedy movie genre had its heyday many years ago – either with the silent classics of Chaplin and Keaton, the absurdist masterpieces of Mel Brooks and the Zucker brothers, or the satirical gems of Elaine May and Albert Brooks – the turn of the 21st century brought along a new movement in Hollywood film comedy pioneered by Judd Apatow and Adam McKay.
Unfortunately, after the Apatow man-child slacker type lost his appeal, comedy filmmakers seemingly gave up on the genre. All-round bombs like Holmes & Watson and Dirty Grandpa certainly did not help enhance the genre’s reputation. Still, there are always funny people who want to make movies, so great comedies will always get made.
11 Team America: World Police (2004)
Trey Parker and Matt Stone’s Team America: World Police is a masterpiece. With the same satirical edge as their groundbreaking animated series South Park, Team America lampoons the reckless destruction, inane plotting, and banal emotional scenes of Bayhem actioners by telling its story with Thunderbirds-style puppets.
It also taps into the blind jingoism of those movies, as the titular squad “polices the world” on behalf of the U.S. government, often failing their missions while leaving behind a path of needless damage. As the icing on the cake, Team America is full of hilarious (and catchy) original songs.
10 Step Brothers (2008)
While Anchorman is the movie that put Adam McKay and Will Ferrell on the map and probably remains their most prevalent work in the pop culture landscape, their greatest collaboration is 2008’s Step Brothers.
Conceived as a vehicle for Ferrell’s on-screen chemistry with John C. Reilly (which reached its peak here), Step Brothers ended up being a spot-on satire of Bush-era America.
9 In Bruges (2008)
Martin McDonagh’s feature directorial debut, In Bruges, explores deep philosophical musings about morality and fate with a generous peppering of pitch-black humor. Colin Farrell and Brendan Gleeson star as two hitmen who are sent to hide out in the titular Belgian city after a job goes awry.
Ralph Fiennes steals the show in the movie’s final act as the duo’s boss, Harry Waters, while McDonagh deftly maintains his own unique comic tone through some pretty heavy plot points.
8 Booksmart (2019)
Olivia Wilde has been swamped with job offers since her directorial debut Booksmart hit theaters. By recapturing the nostalgic tone of John Hughes’ high school comedies while subverting their more problematic elements, Wilde updated a stagnant comedy subgenre for the modern age. But primarily, she told a heartfelt story about friendship, warts and all, that connects emotionally.
Ultimately, what makes Booksmart work as well as it does is the on-screen chemistry shared by stars Beanie Feldstein and Kaitlyn Dever, who are 100% believable as lifelong best friends.
7 The Nice Guys (2016)
Shane Black’s neo-noir comedy thriller The Nice Guys was overshadowed at the box office by Captain America: Civil War and Me Before You. And that’s a real shame, as The Nice Guys was primed to be the beginning of a really great “buddy P.I.” action-comedy franchise.
Ryan Gosling and Russell Crowe shared impeccable chemistry in the lead roles, while Black’s command of story and character as a writer-director is razor-sharp as usual.
6 Tropic Thunder (2008)
Ben Stiller grew up on film sets because his parents were actors, and when he noticed that the stars of war movies returned from the set with the mentality of returning from an actual warzone, the seeds were planted for his absurdist masterpiece Tropic Thunder.
With hilarious supporting turns by Robert Downey, Jr. (who received an Oscar nod) and Jack Black, Tropic Thunder is a pitch-perfect self-aware satire of Hollywood celebrities.
5 What We Do In The Shadows (2014)
Jemaine Clement and Taika Waititi explored what the everyday struggles of vampires would be in their brilliant mockumentary What We Do in the Shadows. The film chronicles a few weeks in the lives of some bloodsuckers living in the suburbs of New Zealand.
Drawing on every facet of vampire fiction for gags, What We Do in the Shadows is the definitive comic deconstruction of the vampire myth.
4 Napoleon Dynamite (2004)
Jared Hess gave every indie comedy director with a shoestring budget and a dream hope that their weird little movie could become a big hit with the unprecedented success of Napoleon Dynamite. This movie is so quirky, it makes Wes Anderson’s films look mainstream.
There’s something about Jon Heder’s (unfortunately) career-defining portrayal of the titular moody, geeky teenager that makes Napolean’s unlikable traits hilarious and strangely endearing.
3 Borat (2006)
Sacha Baron Cohen recently reprised his role as Borat for a sequel that, like its predecessor, captured the zeitgeist and forced America to confront itself at a pivotal political juncture. Borat Subsequent Moviefilm was a rare comedy sequel that lived up to its name and brought new jokes to the table instead of rehashing old ones, but it didn’t quite reach the cultural landmark heights of the original movie.
Despite having an uncompromising comic sensibility, Borat hasn’t aged as poorly as most comedies of its era. Its satire is still just as biting, relevant, and eye-opening today as it was in 2006 when it brought the house down in screenings across the world.
2 Shaun Of The Dead (2004)
The genius of Shaun of the Dead is that there’s a regular romantic comedy buried in its zombie-infested plot. It’s set up like a run-of-the-mill Richard Curtis rom-com as a down-on-his-luck guy gets dumped and decides to sort his life out. Then, the dead come back to life and start eating people. It’s a character-driven movie that happens to feature the undead as gravy.
Edgar Wright established his energetic, inventive directing style in Shaun of the Dead, while Simon Pegg and Nick Frost’s real-life friendship created a lovable on-screen dynamic (as it had done in Spaced and would continue to do in their subsequent collaborations).
1 Bridesmaids (2011)
The Apatow machine has produced a lot of great comedies – like The 40-Year-Old Virgin, Superbad, Knocked Up, and Forgetting Sarah Marshall, to name a few. However, its crowning achievement is arguably Bridesmaids, the perfect cocktail of naturalism, absurdity, and earnest character development.
The movie received two Oscar nominations: Best Original Screenplay, for Kristen Wiig and Annie Mumolo’s beautifully crafted script (allowing enough flexibility for plenty of improv while still telling a tightly structured story), and Best Supporting Actress, for Melissa McCarthy’s scene-stealing supporting performance as Megan.
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