The 15 Best-Written Comedy Movies of The 21st Century

best comedies 21st century

The past fifteen years has been a great time for comedy. From the raunchy to the sophisticated, the 21st century is off to a great start in the comedic film category.

Some of the leading comedy talents of the century such as Judd Apatow, Wes Anderson and Woody Allen can be found on this list. These may not be the best comedies of the 21st century, but they are certainly up there and are certainly well written.


15. Old School (2003)


From the man who would later give us The Hangover trilogy, Todd Phillip, and three of the biggest comedy stars of the 21st century, Will Ferrell, Vince Vaughn, and Owen Wilson, Old School follows three depressed thirty-somethings who seek to re-live their college days by starting a fraternity, and the tribulations they encounter in doing so.

This movie is so funny. When I first heard the premise of this movie, I thought it was kind of a Animal House rip off with older people. I was pleasantly surprised by how funny this was. I was not alone, the film received mixed to positive reviews overall, but audiences have really helped the film succeed. It’s a huge bro movie, enjoyed by groups of guys since its release. It was inducted into Spike Guys’ Choice Awards Guy Movie Hall of Fame in 2012.

I give this film a lot of credit, it moved beyond its somewhat limited premise and went deeper into the men’s lives, the environments that fraternities create, and was actually funny. It may not be the best comedy of the decade, but the writers Todd Phillips, Scot Armstrong, and Court Crandall gave a familiar premise new life and made it hilarious.


14. Tropic Thunder (2008)


A skewering of Hollywood and an unforgettable turn by Robert Downey Jr. make Tropic Thunder a daring, crazy, controversial and funny film. Directed by Ben Stiller, co-written by Stiller, Justin Theroux, and Etan Cohen, Tropic Thunder stars Stiller, Robert Downey Jr., and Jack Black.

The main plot revolves around a group of prima donna actors who are making a fictional Vietnam War film. When their frustrated director decides to drop them in the middle of a jungle, they are forced to rely on their acting skills in order to survive the real action and danger.

The film received generally positive reviews, with critics praising the film’s characters, story, faux trailers, and the performances of Stiller, Downey, and Tom Cruise. It was financially successful and retained the number one position for the first three weekends of release.

There was quite a bit of controversy surrounding some of the jokes about mentally disabilities. Stiller defended the film, stating “We screened the movie so many times and this didn’t come up until very late … in the context of the film I think it’s really clear, they were making fun of the actors and actors who try to use serious subjects to win awards.”

Controversy aside, the performances of the cast received plenty of praise and Downey Jr. received an Academy Award nomination for Best Supporting Actor. Tropic Thunder is bold, funny, and creative, and without the disability comments, the script is one of the best.


13. Mean Girls (2004)

Regina George (Mean Girls)

The film that every millennial has seen at least once, Mean Girls is the ultimate teen comedy from this century. Written by the amazingly talented Tina Fey, and starring her, Lindsay Lohan, Rachel McAdams, and others, Mean Girls is so ridiculously quotable and entered the lexicon of culture probably more than any other comedy film of the last 15 years.

Everyone knows it, everyone has seen it, and it’s hilarious, at least the first time. It’s much smarter and better written than your normal teen comedy. It’s Tina Fey’s masterful script that has allowed the film to hold the test of time. It’s been featured on Best-of lists of the entire decade in publications like Entertainment Weekly and has become a pop-culture phenomenon.

Fans have made GIFs and memes of the film and posted them on social media, including Facebook, Twitter, and Tumblr. I will go back again to Fey’s script which should be recognized as one of the best comedy scripts ever and is the reason we will wanting “fetch” to happen for the rest of our lives.


12. Zoolander (2001)


Zany and out-there are two ways to describe this Ben Stiller led comedy film. Stiller plays the dimwitted Derek Zoolander who becomes the pawn of corrupt fashion executives in order to assassinate the Prime Minister of Malaysia. A ripping satire of the fashion, especially male models, Zoolander received positive reviews upon release, it was commercially successful and has become quite the comedy classic.

From its biting one-liners to Derek Zoolander’s idiotic, yet adorable demeanor, Zoolander is a creative film that uses its cast well. Its cast includes Will Ferrell as the evil Jacobim Mugatu, and Owen Wilson as Derek Zoolander’s rival, the entire cast is hilarious and their characters are so fleshed out and multidimensional.

The use of music is also great and adds to the wacky script. Songs like “Relax” by Frankie Goes to Hollywood and the hilarious scene at the gas station with “Wake Me Up Before You Go Go” by Wham, add lively moments and add to the hilarity.

This past year a sequel was announced at Paris Fashion Week. Zoolander may have a silly concept with even sillier characters, but it is so well written and dynamic that it works.


11. O Brother Where Art Thou? (2000)

O Brother Where Art Thou

The Coen brothers strike gold again. Written, edited, produced, and directed by Joel and Ethan Coen, O Brother Where Art Thou? is a modern satire of Homer’s The Odyssey. Featuring George Clooney, John Turturro, and Tim Blake Nelson as The Soggy Bottom Boys, a fictional folk band, the film has a killer soundtrack starring some of the best names in folk like Emmylou Harris and Alison Krauss.

It’s a different type of comedy than a lot of movies on this list, and a lot of the comedy we saw throughout the decade. The Coen’s brother dark style of comedy, seen in classics like Fargo and Barton Fink, is seen here. The film may not be a laugh riot, but its brand of dark yet witty humor is winning and compliments the rich soundtrack and sepia tone backdrop perfectly.

Although it is adapted from Homer, there is still the Coen touch, an original feeling that a viewer gets while watching a Coen brothers’ work. O Brother Where Art Thou? may not be Coens’ best movie, or even their funniest movie (Fargo in my opinion), it is their comedy tour de force of the 21st century.


10. Juno (2007)

juno movie

Four Academy Award nominations, a number one film soundtrack, extremely positive critical reviews and grossing close to $250 million, unheard of for a comedy. Directed by Jason Reitman and written by Diablo Cody, Juno follows the title character (Ellen Page), an independent-minded teenager confronting an unplanned pregnancy and the subsequent events that put pressures of adult life onto her.

Michael Cera, Jennifer Garner, Jason Bateman, Allison Janney, and J. K. Simmons also star. Cody won the Academy Award for Best Original Screenplay, for a script that was praised by both pro-life and pro-choice supporters for its portrayal of abortion. It was the best reviewed comedy on Rotten Tomatoes for all of 2007 and was placed at the top of Roger Ebert’s and Paste magazine’s lists of best films of 2007.

The character of Juno MacGuff has also received considerable praise with several publications placing her as one of the best characters of the decade. Putting aside all of the awards, nominations, and acclaim aside, Juno is a wonderfully written film that tackles social issues like teenage pregnancy, abortion, and adoption rights.

It presents these issues plainly, and honestly, and does not try to sugarcoat what is going on in Juno’s mind. Diablo Cody’s masterful script tackles these issues and provides plenty of laughs, outside of the mainstream comedy we were used to during the century.


9. Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006)


I know what you’re thinking, how could a film that was mostly real-life interactions with unsuspecting people, be included in a best written list. Borat is included for two reasons mainly, the situations created, and the character of Borat. Sasha Baron Cohen won the 2007 Golden Globe Award for Best Actor: Musical or Comedy, as Borat, while the film was nominated for Best Motion Picture: Musical or Comedy.

The fact that he caricatured an entire country and the idea of being foreign in this country and mocked it for an entire film and still won awards and had American audiences flocking to it is amazing. Borat is one of the ultimate examples of the mockumentary. The reactions he gets from people are just as funny as the character was at the time. People have no idea what to think, it’s so offensive and insensitive that it is hilarious.

The Atlantic Monthly said that it “may be the funniest film in a decade”. The Guardian included the film in its list of ten ‘Best films of the noughties’ (2000–09). In 2014, Baron Cohen decided to retire the character of Borat, along with other popular characters like Bruno and Ali G. It was probably for the best, as people actually know who he is now. However, if we need a refresher, we can always turn to this insane comedic gem.