In researching a response to the question I discovered a fact I had not considered before -- the late 1990's are a treasure trove of comedy gems. Thus, I had to expand the parameters to include this goldmine of guffaws. Comedy has changed considerably since the halcyon days of the 70's and 80's. In some ways it has grown darker and more sophisticated. In other ways it has dispensed with the notion of telling a complete story in favor of the potentially viral joke or block comedy scene. To account for these changes I decided not to limit this list to movies with the most laugh-out-loud moments, but to reward clever and cerebral comedic storytelling as well. Here you will find the high brow and low brow standing shoulder to shoulder.
This list, as with all comedy, is subjective. People tend to have very strong feelings when it comes to the things they laugh at. I invite you to participate in this comedy conversation. Let me know what movies I may have overlooked and why I'm an idiot for thinking this film is funnier than that one. It all goes to a good cause -- reminding my friend that there's still funny to be found.
Without further adieu, I present to you:
The Funniest Movies of the Past 20 Years
1. There's
Something About Mary (1998)
2. Borat (2006)
3. Austin
Powers (1997)
4. South Park: Bigger, Longer, Uncut (1999)
5. The
Big Lebowski (1998)
6. Waiting
for Guffman (1996)
7. Best in
Show (2000)
8. Step Brothers (2008)
9. Office
Space (1999)
10. Anchorman (2004)
11. The 40-Year-Old Virgin (2005)
12. Old
School (2003)
13. Superbad (2007)
14. The
Hangover (2009)
15. Rushmore (1998)
16. Bridesmaids (2011)
17. Knocked
Up (2007)
18. The
Wedding Singer (1998)
19. Ted (2012)
20. Rat Race (2001)
21. The
Royal Tennenbaums (2001)
22. Talladega
Nights (2006)
23. Happy
Gilmore (1996)
24. Harold
& Kumar Go To White Castle (2004)
25. Being
John Malkovich (1999)
26. Elf (2003)
27. The
Dictator (2012)
28. Kingpin (1996)
29. Wedding
Crashers (2005)
30. Jackass:
The Movie (2002)
31. School
of Rock (2003)
32. Election (1999)
33. Bad
Santa (2003)
34. O
Brother, Where Art Thou (2000)
35. The
Grand Budapest Hotel (2014)
36. Tropic
Thunder (2008)
37. Hot Fuzz (2007)
38. Kiss
Kiss Bang Bang (2005)
39. High
Fidelity (2000)
40. Little
Miss Sunshine (2006)
41. Forgetting
Sarah Marshall (2008)
42. Wet Hot
American Summer (2001)
43. American
Pie (1999)
44. This is
the End (2013)
45. Team America:
World Police (2004)
46. Role
Models (2008)
47. Hot Tub
Time Machine (2010)
48. 21 Jump
Street (2012)
49. Meet the
Parents (2000)
50. Bottle
Rocket (1996)
Others Receiving Votes:
Napoleon Dynamite (2004)
Dodgeball (2004)
Dodgeball (2004)
Zoolander (2001)
Cable Guy (1996)
Sideways (2004)
The Pineapple Express (2008)
Shaun of the Dead (2004)
Bowfinger (1999)
Trainwreck (2015)
Easy A (2010)
The Other Guys (2010)
Super Troopers (2001)
Mean Girls (2004)
Road Trip (2000)
Burn After Reading (2008)
Orange County (2002)
Spy (2015)
