THE FUNNIEST MOVIES OF THE PAST 20 YEARS

A couple of weeks ago a longtime friend was bemoaning the sad state of movie comedies these days. In college, we wore out our VHS tapes of Airplane, Animal House, History of the World, Caddyshack, Stripes, Fletch, Vacation, and Meatballs. But where were those comedy classics of today, demanded my frustrated friend. "What are the funniest movies since 2000?" I quickly listed a few titles off the top of my head, but insisted I needed time to conduct a thorough investigation.

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)

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)