The Top 10 Comedy Films Of The 2000s

Frank Martin |

Nov 3, 2022

Will Ferrell in Anchorman, Robert Downey Jr. in Tropic Thunder, and Owen Wilson in Wedding Crashers

At the start of the new millennium, a new order of comedic actors was on the rise. These actors constantly pumped out hit after hit of hilarious films.

Not only did parody and satire get a new breath of life, the dramedy also rose to prominence. These films varied wildly in style and tone, and still hold up two decades later.

10) Waiting

Waiting might not have had the enormous budgets and marketing some of its competitors did, but it had a lot of heart and authenticity about a dysfunctional group of restaurant employees.

The filmmaker took his experience of working in a restaurant and molded a story around it, which is usually how great films are made. The hilarious nature of the dining room, kitchen, and work relationships make for an underrated experience.

9) Scary Movie

Parody movies are nothing new. They’ve been around for decades. However, Scary Movie and its sequels set off a new wave of them in more genres than just horror.

None of them were as funny as this first one, however it is worth noting everything that came afterwards. So many parodies of the 2000s followed this formula and it’s all thanks to this hilariously raunchy film.

8) Shaun of the Dead

Simon Pegg was still an unknown to American audiences when Sean of the Dead rocked both comedy and horror fans alike. It managed to seamlessly combine both genres into something completely new.

The movie featured a very likeable cast and had a different kind of twist to the played out zombie genre. Besides that though, it also offered fans a different kind of ending than one they are probably used to.

7) Borat

Fans were really just starting to come to grips with the comedic madness of Sacha Baron Cohen when Borat first came out. Quite possibly, the comedic landscape still hasn’t recovered yet.

The movie was offensive and insulting in all the right ways. He caused just enough outrage to get people interested, which is what good comedy, especially improvisational comedy, is supposed to do.

6) Anchorman

If it wasn’t clear to audiences that Will Ferrell was a force to be reckoned with then Anchorman certainly put him on the map. Ron Burgundy, too, became a cultural force in his own right.

The film featured an all-star cast that took the ’70s to a ridiculous extreme. More than that though, it also tackled the subject of sexism in the workplace in hilarious fashion.

5) Superbad

Superbad is a relatively bizarre film. It was written by Seth Rogen when he was an immature kid and decided to leave all of the immature jokes in there when they filmed it as an adult.

It’s raunchy and completely unapologetic. The plot is as basic as it can be about kids simply trying to get laid at a party. Yet surprisingly, the film has a lot of heart to go along with its laughs.

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4) Knocked Up

Knocked Up exemplified a certain kind of trend in 2000s comedy. Meaning, it featured films that tried to deal with everyday situations in a humorous yet dramatic matter.

It also set up Seth Rogen and his fellow cast of potheads as the comedy actors to look out for during the decade. This doesn’t even take into accounts Katherine Heigl’s fun portrayal of a successful woman knocked up by Seth Rogen’s doofy character.

3) Tropic Thunder

It’s hard to think of a comedy in the 2000s that had a more impressive cast than Tropic Thunder. Ben Stiller helmed the film, but it was Jack Black, Tom Cruise, Danny McBride, and Robert Downey Jr. that made it something special.

Besides the absurdist dialogue, the film took war action to a ridiculous extreme. There were explosions, shootouts, and so much violence in the jungle that its cast of idiots didn’t know how to handle themselves.

2) Old School

Old School was right on the cusp of transitioning between the ’90s era of comedy and the 2000s. It was definitely the right film for the right time to have audiences introduced into something new.

Vince Vaughn, Luke Wilson, and Will Ferrell worked hilariously together to depict old men reliving their college fantasies. The movie delivered a plethora of memorable dialogue while also featuring a hilarious Jeremy Piven.

1) Wedding Crashers

It’s hard to find any aspect of Wedding Crashes that doesn’t measure up to hilarious proportions. The film is about Vince Vaughn and Owen Wilson crashing weddings to sleep with women, and they are very good at it.

They run into trouble when they try to crash the wedding of Christopher Walken’s daughter. More than that though, the film also features the likes of Bradley Cooper, Isla Fisher, and even Rachel McAdams. With all of their forces combined, Wedding Crashers is something to remember.

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