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Comedy is by far among the most subjective type of filmmaking out there (right next to horror, we’d say). However, even though moviegoers may have vastly different opinions of what is truly funny, some films still manage to break through and become recognized for the innovative ways they manage to elicit laughter and the sheer number of laughs per minute they can inspire in audiences. Focusing specifically on films released since 1996, here are the 10 best comedy movies released since that have stood the test of time.

1. There’s Something about Mary (1998)

Back in the late 1990s, this Farrelly Brothers film shocked audiences with its gross-out gags and outrageous, blatantly offensive sense of humor. However, the sharp performances from Ben Stiller, Cameron Diaz, and Matt Dillon have helped it transcend that era to emerge an enduring favorite among comedy aficionados.

2. The Big Lebowski (1998)

Joel and Ethan Coen are regularly regarded among the best filmmakers working today, but this is probably among the goofiest films of their filmography. Jeff Bridges created an icon in his turn as The Dude, launching a zillion memes and quotable lines alongside co-stars John Goodman and John Turturro.

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3. Office Space (1999)

Although this comedy from Mike Judge (King of the Hill) was a box office bomb, it has since earned a reputation as one of the most relatable comedies ever made. Office Space is just a barrage of laugh-out-loud moments and memorable lines. No one who has seen this has ever looked at office work the same way again.

4. Shaun of the Dead (2004)

The first in the Blood and Ice Cream (or Three Flavors Cornetto) trilogy, this spoof of zombie films made veritable stars of all involved. Director Edgar Wright instantly earned a global fanbase, and stars Simon Pegg, and Nick Frost went on to share the screen several more times. Be sure to check out Hot Fuzz and The World’s End as well.

5. Anchorman: The Legend of Ron Burgundy (2004)

Will Ferrell has headlined so many hit comedies, but none has had the cultural impact of his initial turn as the pompous titular newscaster in this Adam McKay film. So many hilarious lines and memorable characters that viewers will find themselves trapped in a glass case of emotion, unable to stop the laughter.

6. Mean Girls (2004)

This Tina Fey-scripted teen comedy set a new gold standard for what that particular subgenre can look like in the modern age. Buoyed by flawless performances by Lindsay Lohan and Rachel McAdams, Mean Girls appears to be more relevant than ever before. That’s no small feat for a film that’s already more than a decade old.

7. The 40-Year-Old Virgin (2005)

Steve Carell and filmmaker Judd Apatow are two of the hottest names in Hollywood now. However, since this film was released, Carell has become an Oscar-nominated actor, and Apatow is essentially his own brand. This perfectly cast and surprisingly sweet film still stands as perhaps the best work either has done on the big screen.

8. Borat (2006)

Fans of Da Ali G Show knew that Sacha Baron Cohen was one of the most fearless comic talents in recent memory. Borat made that announcement to the world, as its star took tremendous creative risks to satirize our own society, earning an Oscar nomination for Best Adapted Screenplay in the process.

9. Bridesmaids (2011)

Whether you loved or hated the Ghostbusters reboot, director Paul Feig proved with this Kristen Wiig-led comedy that he has a knack for giving funny ladies a place to showcase their talents. Melissa McCarthy, as well as screenwriters Wiig and Annie Mumolo, received Oscar nominations, and Hollywood finally realized that female-led comedies can succeed at the box office.

10. 21 Jump Street (2012)

Reboots are coming fast and furious these days, and 21 Jump Street — based on the 1980s TV show — deftly commented on its own place among that trend. Meanwhile, stars Channing Tatum and Jonah Hill deliver uproarious performances that still have us hoping that a third Jump Street film eventually comes to pass.

What’s your favorite comedy of the past 20 years? Share your thoughts in the comments section below.

Robert Yaniz Jr.
Robert Yaniz Jr. has been a professional writer since 2003 and a student of pop culture long before that. If he had a nickel for each hour he spent gazing up at a screen in a darkened theater, he would be far too busy swimming around his Scrooge McDuck-style vault to write anything for the Internet. As it stands, you can find his musings on the entertainment world at or chat movies with him directly on Twitter @crookedtable.