My Fave Five 2000s Comedy Films

Hello, friends!

One of my favorite film genres is comedy. If you’ve followed me for any amount of time, you probably already knew that. They say laughter is the best medicine and I enjoy a good laugh. When getting this post together, I was thinking about doing my fave five comedy films of all time. However, seeing as how we are in the middle of the Ultimate 2000s Blogathon, I decided to instead focus specifically on that decade. It is difficult compiling a list of my top all time favorite comedy films but it was a little harder of a challenge to come up with my top comedies of the 2000s. After some toiling, here are my five favorite 2000s comedy films.

Step Brothers movie poster5) Step Brothers

Will Ferrell and John C. Reilly were a powerhouse comedy duo of the 2000s. Step Brothers was the second film they lead together, the first being Talladega Nights: The Ballad of Ricky Bobby and the most recent was 2018’s Holmes and Watson. While I laugh during Talladega Nights, I laugh hysterically during Step Brothers. Ferrell and director Adam McKay took what made Talladega Nights a hit and refined it, creating more memorable scenes, laugh-out-loud moments, and instantly quotable lines. Say what you will about Ferrell and Reilly, but they have some of the best comedic chemistry of our time. Add in Mary Steenburgen, Richard Jenkins, Adam Scott, and Kathryn Hahn and you have a cast any comedy film will be jealous of.

Superbad movie poster4) Superbad

Towards the end of the first decade of the 2000s, Michael Cera was moving from television onto the big screen. That transition was a gift from the movie gods. Cera’s deadpan delivery and comedic timing are gifts to cinema. He plays the awkward teen like no other actor I have seen, making him the perfect fit to play Evan, a kid who wants to throw the perfect party for the girl of his dreams. Next to him is Jonah Hill playing Seth, who is more confident but just as awkward as Evan. Christopher Mintz-Plasse makes one of the best acting debuts as Fogell, aka McLovin. Written by Seth Rogen, whom Hill’s character is named after, Superbad is one of the funniest yet most accurate depictions of what it’s like to be a high schooler.

Dodgeball: A True Underdog Story movie poster3) Dodgeball: A True Underdog Story

Everybody loves a good underdog story. Dodgeball: A True Underdog Story takes the well-known sports movie cliches and parodies them; taking a team of misfits and showing them work their way from unlikely team to dodgeball champions. Lead by Peter Le Fleur (Vince Vaughn), the Average Joe’s Gym is fighting to keep their gym getting bought by Globo Gym, lead by White Goodman (Ben Stiller). For me, Stiller is what makes this film so funny. Yes, Vaughn is great, but Stiller has some of the best lines in the film and adds such a flare to his delivery that makes his delivery all the better. The comedy is such a product of its time but Dodgeball proved what that decade-defining humor could be at its best.

Wedding Crashers movie poster2) Wedding Crashers

Every movie on this list so far are outstanding because the lead duos play off each other so well. Wedding Crashers is no exception, and probably the best example on this list of how a pair with fantastic chemistry can elevate a movie. Owen Wilson and Vince Vaughn, Vaughn’s second appearance on this list, play two best friends who crash weddings to get laid. There is a set of “Crasher Rules” that Jeremy (Wilson) and John (Vaughn) are always throwing back and forth at each other, which I’ve always thought was entertaining. The beautiful ladies Amy McAdams and Isla Fisher prove that they have just as much comedic talent as the boys. If I ever need a film for a quick pick-me-up, this is high on my list.

The Hangover movie poster1) The Hangover

Almost anyone who has had a night of partying and drinking has had to deal with a hangover the next morning. Like any great comedy, The Hangover takes something as common as dealing with drinking too much and cranks the craziness to max. They say “two is a party, three is a crowd” but that does not apply to this film. Zack Galifianakis gets my vote as the actor with the best lines in the film but really, Galifianakis, Bradley Cooper, and Ed Helms all have their own stand-out moments. Plus, there are plenty of cameos in this road trip-esque film that each scene is unique and funny on its own. Not only is The Hangover my favorite comedy of the decade, it is one of my favorite comedies of all time.


Honorable mentions include Bruce Almighty, School of Rock, The 40 Year Old Virgin, EuroTrip, and Talladega Nights: The Ballad of Ricky Bobby.

If you want to check out any of the entries for the Ultimate 2000s Blogathon, you can see a list of all of them here.

What are some of your favorite comedies from the 2000s?

Until next time, cheers!

11 thoughts on “My Fave Five 2000s Comedy Films

  1. What a great decade for comedy! I would add “Tropic Thunder”, although you could call it an “Action comedy”…it was a decade of raucous humor, “buddy” comedies and a surprising amount of warmth and emotion!

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  2. These are all fantastic. Tropic Thunder is a great one too. I’d probably add Shaun of the Dead, Hot Fuzz… Wait, is it against the rule if they’re all Edgar Wright comedies? πŸ˜‚

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