The Funniest Movies of the Decade (2000-2009)

Continuing with the Best of the Decade series this month, LwB has the Funniest Movies of the Decade. No matter how many times I see these films, I still laugh hysterically. In the past ten years, I’ve constantly repeated great lines from these movies to the annoyance of my friends and family everywhere.

tropic-thunder-poster10. Tropic Thunder (2008)
Robert Downey Jr playing a black guy? That concept alone makes this film great. Then I saw how well he pulled it off. Jack Black and Tom Cruise do a phenomenal job as well. No disrespect to the late Heath Ledger, but Robert Downey Jr. should have won best supporting actor for his performance.
Robert Downey Jr. talks about his role





americanpie29. American Pie 2 (2001)
This movie was just as good as the original, if not better.  As usual, there were a number of memorable, outrageous scenes from Stifler, Jim and the rest of the crew.
Best Stifler Moments






hangover8.The Hangover (2009)
This is the most recent movie to make the list and the only one on here I haven’t watched several times. Once it gets to HBO, I’ll be sure to watch it over and over. The scene where they wake up the morning after is hysterical.
The morning after scene






harold_and_kumar_go_to_white_castle7.  Harold & Kumar Go to White Castle (2004)
I knew this would be a classic comedy once I saw the scene where Harold and Kumar pick up a hitchhiking Doogie Howser on ecstasy.  That scene alone makes it one of the funniest movies of the decade.
Doogie Howser Scene






SuperBad_Movie6. Superbad (2007)
This is a hilarious movie that catapulted Jonah Hill into stardom. What I love about this movie is that it portrays the awkwardness of being a teenager so well.  Jonah Hill finds some creative new ways to describe having sex in this flick also.  My goal is to be the iron chef of pounding vag.
Great Superbad clips





old school5. Old School (2003)
This comedy has it all: Frank the Tank, the foul-mouthed wedding singer, Blue, and a great shot of Elisha Cuthbert’s ass in booty shorts.  It’s a classic comedy.
I think this is pretty much everyone’s favorite Old School scene.






borat4. Borat (2006)
Sascha Baron Cohen should have gotten the Academy Award for Best Actor for this movie.  I don’t know how he was able to stay in character so well. The movie’s humor is based on its shock value, so it loses its luster after watching it a couple times. However, I can’t remember laughing harder at a movie the first time I saw it.
I couldn’t find many clips online. This is the funniest clip I could find.





wedding_crashers3. Wedding Crashers (2005)
I pretty much enjoy every Vince Vaughn movie. I also enjoy almost every Owen Wilson film. Putting them together is a great formula for non-stop laughter. Both were great in this movie, however it was Will Ferrell’s five minute appearance that stole the show.






40-year-old_virgin2. 40 Year Old Virgin (2005)
This is a close second to the funniest movies of the decade. Steve Carell plays this role of an awkward, sexually confused 40-year old so well. There are so many great scenes and lines from this movie that they had to cut a number of great parts out. The extended movie on DVD has so many other awesome scenes that never made it past the cutting room floor.
Funniest 40-Year Old Virgin Scene




anchorman1. Anchorman (2004)
Anchorman tops the list of the funniest movies of the decade. This is, by far, Will Ferrell’s best movie.  The movie is chock-full of great one-liners, many of which have become mainstream in pop-culture.  It’s so difficult to pick my favorite scene because there are so many….but here it is.
My favorite Anchorman Clip (extended version)




Honorable Mention Movies: Meet the Parents, You, Me and Dupree, Little Miss Sunshine, Zoolander, Knocked Up, Forgetting Sarah Marshall, Idiocracy

What was your favorite movie? Agree with the list? Disagree. Comment about it!

7 comments for “The Funniest Movies of the Decade (2000-2009)

  1. Laura
    December 10, 2009 at 1:27 pm

    MA!!! The MEATLOAF!!

  2. December 10, 2009 at 4:24 pm

    Loving this list! All those movies are absolutely fantastic and hilarious!
    .-= E.P.´s last blog ..Endings and beginnings =-.

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  4. December 12, 2009 at 2:41 am

    Thank goodness Super Troopers didn’t make the list!
    .-= Aaron´s last blog ..Biggest Loser Season 8: The Final Four =-.

  5. Bro
    December 12, 2009 at 6:55 pm

    I’m going to have to disagree with you on Anchorman as #1. 40-year-old Virgin is #1, although I’ve had near brawls with people over 40-year-old Virigin v. Wedding Crashers.

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  7. Free Comedy Movies
    January 19, 2010 at 4:49 am

    Thanks for the list. Comedy movies are my fave. I love horror movies too!

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