Top 20 Comedies of the Last 20 Years

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1.
The 40-Year-Old Virgin (2005)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
Goaded by his buddies, a nerdy guy who's never "done the deed" only finds the pressure mounting when he meets a single mother. (116 mins.)
Director: Judd Apatow
 
2.
Knocked Up (2007)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
For fun-loving party animal Ben Stone, the last thing he ever expected was for his one-night stand to show up on his doorstep eight weeks later to tell him she's pregnant with his child. (129 mins.)
Director: Judd Apatow
 
3.
Anchorman: The Legend of Ron Burgundy (2004)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Ron Burgundy is San Diego's top-rated newsman in the male-dominated broadcasting of the 1970s, but that's all about to change for Ron and his cronies when an ambitious woman is hired as a new anchor. (94 mins.)
Director: Adam McKay
 
4.
The Hangover (2009)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Three buddies wake up from a bachelor party in Las Vegas, with no memory of the previous night and the bachelor missing. They make their way around the city in order to find their friend before his wedding. (100 mins.)
Director: Todd Phillips
 
5.
Funny People (2009)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
When seasoned comedian George Simmons learns of his terminal, inoperable health condition, his desire to form a genuine friendship causes him to take a relatively green performer under his wing as his opening act. (146 mins.)
Director: Judd Apatow
 
6.
Superbad (2007)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Two co-dependent high school seniors are forced to deal with separation anxiety after their plan to stage a booze-soaked party goes awry. (113 mins.)
Director: Greg Mottola
 
7.
Old School (2003)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Three friends attempt to recapture their glory days by opening up a fraternity near their alma mater. (88 mins.)
Director: Todd Phillips
 
8.
Anger Management (2003)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
Dave Buznik is a businessman who is wrongly sentenced to an anger-management program, where he meets an aggressive instructor. (106 mins.)
Director: Peter Segal
 
9.
Liar Liar (1997)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A fast track lawyer can't lie for 24 hours due to his son's birthday wish after the lawyer turns his son down for the last time. (86 mins.)
Director: Tom Shadyac
 
10.
The Other Guys (2010)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
Two mismatched New York City detectives seize an opportunity to step up like the city's top cops whom they idolize -- only things don't quite go as planned. (107 mins.)
Director: Adam McKay
 
11.
Wedding Crashers (2005)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
John Beckwith and Jeremy Grey, a pair of committed womanizers who sneak into weddings to take advantage of the romantic tinge in the air, find themselves at odds with one another when John meets and falls for Claire Cleary. (119 mins.)
Director: David Dobkin
 
12.
Big Daddy (1999)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
A lazy law school grad adopts a kid to impress his girlfriend, but everything doesn't go as planned and he becomes the unlikely foster father. (93 mins.)
Director: Dennis Dugan
 
13.
Happy Gilmore (1996)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
A rejected hockey player puts his skills to the golf course to save his grandmother's house. (92 mins.)
Director: Dennis Dugan
 
14.
Black Sheep (1996)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
A gubernatorial candidate hires a wormy special assistant whose only job is to make sure the candidate's well-meaning but incompetent brother doesn't ruin the election. (87 mins.)
 
15.
Austin Powers: International Man of Mystery (1997)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
A 1960s hipster secret agent is brought out of cryofreeze to oppose his greatest enemy in the 1990s, where his social attitudes are glaringly out of place. (94 mins.)
Director: Jay Roach
 
16.
Meet the Parents (2000)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Male nurse Greg Focker meets his girlfriend's parents before proposing, but her suspicious father is every date's worst nightmare. (108 mins.)
Director: Jay Roach
 
17.
Bruce Almighty (2003)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A guy who complains about God too often is given almighty powers to teach him how difficult it is to run the world. (101 mins.)
Director: Tom Shadyac
 
18.
Get Smart (2008)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
A highly intellectual but socially awkward spy is tasked with preventing a terrorist attack from a Russian spy agency. (110 mins.)
Director: Peter Segal
 
19.
Forgetting Sarah Marshall (2008)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Devastated Peter takes a Hawaiian vacation in order to deal with the recent break-up with his TV star girlfriend, Sarah. Little does he know, Sarah's traveling to the same resort as her ex - and she's bringing along her new boyfriend. (111 mins.)
 
20.
Ace Ventura: Pet Detective (1994)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
A goofy detective specializing in animals goes in search of a missing dolphin mascot of a football team. (86 mins.)
Director: Tom Shadyac