The Best Comedies Of The 21st Century (So Far), Ranked

Summary

• Contemporary comedies are returning to the raunchy, subversive style of the 1980s.
• Satire and parody are as popular as ever in modern comedy, with a focus on superheroes and remakes.
• International markets and new movements pioneered by directors like Judd Apatow are shaping the evolution of comedy.

The tradition of comedy movies goes back to the silent classics of Chaplin and Keaton, and modern times saw the absurdist masterpieces of Mel Brooks and the Zucker brothers, which evolved into 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.

Newer comedies seem to be returning to the raunchy and often subversive comedy of the 1980s when movies like Caddyshack and Revenge of the Nerds made headlines with their controversial dialogues and outlandish situations. Contemporary comic genius can include everything from airplanes to superheroes, and in addition to the American production companies, there’s also the international market to consider.

Updated December 12, 2024, by Kristy Ambrose: The big comedies of recent years, like almost every other movie these days, are related to either superheroes or remakes of classic sitcoms. Despite lacking creativity, some of these comedies have used experimental or subversive ways to tell their stories while making the audience laugh. R-rated comedies are back in style, and parody and absurdist humor are as popular as ever, so even though it feels like everything has been done, that’s not really the case.

13 Team America: World Police

A Musical From The Makers Of South Park

• Director: Trey Parker
• Distributor: Paramount Pictures
• Starring: Trey Parker, Matt Stone, Kristen Miller, Masasa Moyo
• Release Date: October 15, 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.

12 Step Brothers

Ferrell And McKay’s Best Team-up

• Director: Adam McKay
• Distributor: Sony Pictures Releasing
• Starring: Will Ferrell, John C. Reilly, Richard Jenkins, Mary Steenburgen
• Release Date: July 25, 2008

While Anchorman 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.

The movie has a simple plot that could have been written for a sitcom. Adult children Brennan Huff and Dale Doback still live with their parents, and when those parents get married, the two of them have to live together as stepbrothers. It sounds simple, but the outcomes are hilarious.

11 In Bruges

Black Humor And Hitmen

• Director: Martin McDonagh
• Distributor: Focus Features, Universal Pictures
• Starring: Colin Farrell, Brendan Gleeson, Ralph Fiennes, Clémence Poésy
• Release Date: February 8, 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.

10 Booksmart

A Classic Teen Comedy

• Director: Olivia Wilde
• Distributor: United Artists Releasing
• Starring: Kaitlyn Dever, Beanie Feldstein, Jessica Williams, Lisa Kudrow
• Release Date: May 24, 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.

9 Deadpool

The Merc With The Mouth

• Director: Tim Miller
• Distributor: 20th Century Fox
• Starring: Ryan Reynolds, Morena Baccarin, Gina Carano, Brianna Hildebrand
• Release Date: February 12, 2016

It’s easy to forget that this movie almost didn’t get made. But thanks to the efforts of Ryan Renolds, some daring writers, and some suspiciously-timed leaked footage, there’s a whole Deadpool franchise that just released another blockbuster. Deadpool & Wolverineis the first movie featuring the superhero after the copyright moved to Disney, but now that raunch sells, there’s nothing Deadpool can’t do.

Studios and producers had soured on the idea of R-rated comedies, but the public felt differently. When Deadpool was finally released, it was a hit and paid for itself in a matter of days. Deadpool is a parody and satire type of comedy, making fun of superhero movie tropes while also using them to tell their story.

8 The Nice Guys

A Neo-Noir Comedy Thriller

• Director: Shane Black
• Distributor: Warner Bros. Pictures, Bloom
• Starring: Russell Crowe, Ryan Gosling, Angourie Rice, Matt Bomer
• Release Date: May 20, 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.

7 Tropic Thunder

The Best Of Ben Stiller

• Director: Ben Stiller
• Distributor: DreamWorks Pictures, Red Hour Productions
• Starring: Jack Black, Robert Downey Jr., Steve Coogan, Jay Baruchel
• Release Date: August 13, 2008

Ben Stiller grew up on film sets because his parents were actors. 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. This movie is a masterpiece of parody, writing, and comedic timing.

The cast, which includes the director in the starring role, is also impressive. 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.

6 What We Do In The Shadows

Vampire Life In New Zealand

• Directors: Jemaine Clement, Taika Waititi
• Distributor: Madman Entertainment, Unison/Paladin
• Starring: Jonathan Brugh, Cori Gonzalez-Macuer, Stu Rutherford
• Release Date: February 13, 2015

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.

5 21 Jump Street

Everyone’s Favorite SitCom Remake

• Directors: Phil Lord, Christopher Miller
• Distributor: Columbia Pictures, Metro-Goldwyn-Mayer
• Starring: Jonah Hill, Channing Tatum, Brie Larson, Dave Franco
• Release Date: March 16, 2012

21 Jump Street is based on a sitcom from the late 1980s, but the dialogue and twists on the typical situations hide some surprisingly dark jokes and unexpected consequences. It’s as if a contemporary writer wanted to take a 1980s buddy-cop show and write in a hyperrealistic way. The result is a hilarious satire on both teen and police movies.

The “friends” relationship at the core of this story starts when the main characters, Morton Schmidt and Greg Jenko, meet in the police academy after years of being at odds with each other in high school. Eventually, they end up as undercover agents in a high school, looking for a dangerous drug, which is a genre trope as old as time.

4 Napoleon Dynamite

Offbeat, Quirky, And Hysterically Funny

• Director: Jared Hess
• Distributor: Fox Searchlight Pictures, Paramount Pictures, MTV Films
• Starring: Jon Heder, Jon Gries, Aaron Ruell, Efren Ramirez
• Release Date: June 11, 2004

Jared Hess gave every indie comedy director 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 that it makes Wes Anderson’s films look mainstream.

There’s something about Jon Heder’s career-defining portrayal of the titular moody, geeky teenager that makes Napolean’s unlikable traits hilarious and strangely endearing. He’s supported by many equally lovable and unique characters.

3 Borat

The Mockumentary Of The Century

• Director: Larry Charles
• Distributor: 20th Century Fox
• Starring: Sacha Baron Cohen
• Release Date: November 3, 2006

Despite having an uncompromising comic sensibility, the original 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.

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.

2 Shaun Of The Dead

One Of The “Three Flavours Cornetto” Movie Trilogy

• Director: Edgar Wright
• Distributor: Universal Pictures, Rogue Pictures, Mars Distribution
• Starring: Simon Pegg, Kate Ashfield, Lucy Davis, Nick Frost, Dylan Moran
• Release Date: September 24, 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

The Oscar-Nominated Comedy

• Director: Paul Feig
• Distributor: Universal Pictures
• Starring: Kristen Wiig, Maya Rudolph, Rose Byrne, Wendi McLendon-Covey
• Release Date: May 13, 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 could be 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.