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The Funniest Movies of the 2000s 

Ranker Film
Originally by
Updated March 25, 2020 100.4k votes 6.3k voters 222k views 125 items

List Rules Vote up the comedies and dramatic comedy films released between January 2000 and December 2009 that make you laugh the hardest.

Here is a list of the funniest movies of the 2000s. These titles are the names of the greatest comedy films released in the 2000-2009 range of hilarity. Judd Apatow and Steve Carell struck comedy gold with The 40-Year-Old Virgin, as he continued when he forgot Sarah Marshall and knocked up Katherine Heigl. Comedies of the 2000s came in the form of the ultra absurd; take a look at the montage scenes in Wet Hot American Summer. The funniest movies also were indie packages, as was the case with Little Miss Sunshine, an equally wonderful comedy where Carell couldn't be playing more polar characters. O Brother, Where Art Thou? and Eight Crazy Nights made millions laugh their butts off, as did comedy films like Elf and Meet The Parents. This list compiles those comedies that landed on the silver screens and changed the landscape for funny movies - some of which were overlooked at the time but have since gained dedicated audiences. Or, they made the list because they were just plain hilarious.

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1
The Hangover is listed (or ranked) 1 on the list The Funniest Movies of the 2000s
Mike Tyson, Bradley Cooper, Heather Graham

Released: 2009

Directed by: Todd Phillips

The Hangover is a 2009 American comedy film, co-produced and directed by Todd Phillips and written by Jon Lucas and Scott Moore. It is the first film of The Hangover trilogy. The film stars ...more

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2
The 40-Year-Old Virgin ... is listed (or ranked) 2 on the list The Funniest Movies of the 2000s
Elizabeth Banks, Kat Dennings, Steve Carell

Released: 2005

Directed by: Judd Apatow

The 40-Year-Old Virgin is a 2005 American romantic comedy film written, produced and directed by Judd Apatow, about a middle-aged man's journey to finally lose their virginity. It was co-written ...more

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3
Anchorman: The Legend of... is listed (or ranked) 3 on the list The Funniest Movies of the 2000s
Christina Applegate, Will Ferrell, Ben Stiller

Released: 2004

Directed by: Adam McKay

Anchorman: The Legend of Ron Burgundy, or simply Anchorman, is a 2004 comedy film directed by Adam McKay, produced by Judd Apatow, starring Will Ferrell, and written by McKay and Ferrell. The ...more

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4
Elf is listed (or ranked) 4 on the list The Funniest Movies of the 2000s
Zooey Deschanel, Will Ferrell, Peter Dinklage

Released: 2003

Directed by: Jon Favreau filmography

Elf is a 2003 American Christmas comedy film directed by Jon Favreau and written by David Berenbaum. It stars Will Ferrell, James Caan, Bob Newhart, Ed Asner, and Zooey Deschanel. It was ...more

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5
Step Brothers is listed (or ranked) 5 on the list The Funniest Movies of the 2000s
wiabux added Will Ferrell, Seth Rogen, Mary Steenburgen

Released: 2008

Directed by: Adam McKay

Step Brothers is a 2008 American buddy slapstick comedy film starring Will Ferrell and John C. Reilly. The screenplay was written by Will Ferrell and Adam McKay, from a story written by them ...more

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6
Superbad is listed (or ranked) 6 on the list The Funniest Movies of the 2000s
Emma Stone, Seth Rogen, Jonah Hill

Released: 2007

Directed by: Greg Mottola

Superbad is a 2007 American teen comedy film directed by Greg Mottola and starring Jonah Hill and Michael Cera. The film was written by Seth Rogen and Evan Goldberg, who began working on the ...more

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7
Old School is listed (or ranked) 7 on the list The Funniest Movies of the 2000s
Elisha Cuthbert, Snoop Dogg, Will Ferrell

Released: 2003

Directed by: Todd Phillips

Old School is a 2003 American comedy film released by DreamWorks Pictures and The Montecito Picture Company and directed by Todd Phillips. The story was written by Court Crandall, and the film ...more

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8
Wedding Crashers is listed (or ranked) 8 on the list The Funniest Movies of the 2000s
Owen Wilson, Vince Vaughn, Christopher Walken

Released: 2005

Directed by: David Dobkin

Wedding Crashers is a 2005 American comedy film directed by David Dobkin. John Beckwith (Owen Wilson) and Jeremy Grey (Vince Vaughn), a pair of committed womanizers who sneak into weddings to ...more

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9
Meet the Parents is listed (or ranked) 9 on the list The Funniest Movies of the 2000s
Robert De Niro, Ben Stiller, Owen Wilson

Released: 2000

Directed by: Jay Roach

Meet the Parents is a 2000 American comedy film directed by Jay Roach. Male nurse Greg Focker (Ben Stiller) meets his girlfriend's parents before proposing, but her suspicious father (robert De ...more

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10
DodgeBall: A True Underd... is listed (or ranked) 10 on the list The Funniest Movies of the 2000s
wiabux added Ben Stiller, Chuck Norris, Vince Vaughn

Released: 2004

Directed by: Rawson Marshall Thurber

DodgeBall: A True Underdog Story, commonly referred to as DodgeBall, is a 2004 American sports comedy film produced by 20th Century Fox and Red Hour Productions, written and directed by Rawson ...more

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11
Shrek is listed (or ranked) 11 on the list The Funniest Movies of the 2000s
Cameron Diaz, Eddie Murphy, Mike Myers

Released: 2001

Directed by: Andrew Adamson, Vicky Jenson

Shrek is a 2001 American computer-animated fantasy-comedy film produced by PDI/DreamWorks, released by DreamWorks Pictures, directed by Andrew Adamson and Vicky Jenson, featuring the voices of ...more

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12
Monsters, Inc. is listed (or ranked) 12 on the list The Funniest Movies of the 2000s
pmmom38 added Billy Crystal, John Goodman, Steve Buscemi

Released: 2001

Directed by: David Silverman, Pete Docter, Lee Unkrich

Monsters, Inc. is a 2001 American computer-animated comedy film directed by Pete Docter, produced by Pixar Animation Studios, and released by Walt Disney Pictures. John Lasseter and Andrew ...more

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13
Mean Girls is listed (or ranked) 13 on the list The Funniest Movies of the 2000s
Lindsay Lohan, Rachel McAdams, Amanda Seyfried

Released: 2004

Directed by: Mark Waters

Mean Girls is a 2004 American teen comedy film. Mark Waters directed, and Tina Fey wrote the screenplay, which is based in part on Rosalind Wiseman's non-fiction book Queen Bees and Wannabes, ...more

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14
Super Troopers is listed (or ranked) 14 on the list The Funniest Movies of the 2000s
Lynda Carter, Brian Cox, Jim Gaffigan

Released: 2001

Directed by: Jay Chandrasekhar

Super Troopers is a 2001 comedy film directed by Jay Chandrasekhar, written by and starring the Broken Lizard comedy group. Marisa Coughlan, Daniel von Bargen and Brian Cox co-star while Lynda ...more

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15
Forgetting Sarah Marshal... is listed (or ranked) 15 on the list The Funniest Movies of the 2000s
Mila Kunis, Kristen Bell, Russell Brand

Released: 2008

Directed by: Nicholas Stoller

Forgetting Sarah Marshall is a 2008 American romantic comedy-drama film directed by Nicholas Stoller and starring Jason Segel, Kristen Bell, Mila Kunis and Russell Brand. The film, which was ...more

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16
The Other Guys is listed (or ranked) 16 on the list The Funniest Movies of the 2000s
Eva Mendes, Dwayne Johnson, Mark Wahlberg

Released: 2010

Directed by: Adam McKay

The Other Guys is a 2010 action comedy film directed and co-written by Adam McKay, starring Will Ferrell and Mark Wahlberg, and featuring Michael Keaton, Eva Mendes, Steve Coogan, Ray Stevenson, ...more

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17
Bruce Almighty is listed (or ranked) 17 on the list The Funniest Movies of the 2000s
Jennifer Aniston, Jim Carrey, Morgan Freeman

Released: 2003

Directed by: Tom Shadyac

Bruce Almighty is a 2003 American religious comedy-drama film directed by Tom Shadyac, written by Steve Koren, Mark O'Keefe and Steve Oedekerk and stars Jim Carrey as Bruce Nolan, a ...more

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18
50 First Dates is listed (or ranked) 18 on the list The Funniest Movies of the 2000s
looksharp added Drew Barrymore, Adam Sandler, Dan Aykroyd

Released: 2004

Directed by: Peter Segal

50 First Dates is a 2004 American romantic comedy film directed by Peter Segal and written by George Wing. The film stars Adam Sandler as a lothario veterinarian and Drew Barrymore as an ...more

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19
Zombieland is listed (or ranked) 19 on the list The Funniest Movies of the 2000s
wiabux added Emma Stone, Amber Heard, Bill Murray

Released: 2009

Directed by: Ruben Fleischer

Zombieland is a 2009 American zombie comedy film directed by Ruben Fleischer from a screenplay written by Rhett Reese and Paul Wernick. The film stars Jesse Eisenberg, Woody Harrelson, Emma ...more

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20
Tropic Thunder is listed (or ranked) 20 on the list The Funniest Movies of the 2000s
wiabux added Ben Stiller, Jack Black, Robert Downey Jr.

Released: 2008

Directed by: Ben Stiller

Tropic Thunder is a 2008 American action satire comedy film directed by Ben Stiller. Through a series of freak occurrences, a group of actors shooting a big-budget war movie are forced to become ...more

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21
Pineapple Express is listed (or ranked) 21 on the list The Funniest Movies of the 2000s
wiabux added Seth Rogen, James Franco, Gary Cole

Released: 2008

Directed by: David Gordon Green

Pineapple Express is a 2008 American buddy stoner action comedy film directed by David Gordon Green. A process server (Seth Rogen) and his marijuana dealer (James Franco) are forced to flee from ...more

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22
Shaun of the Dead is listed (or ranked) 22 on the list The Funniest Movies of the 2000s
Martin Freeman, Simon Pegg, Bill Nighy

Released: 2004

Directed by: Edgar Wright

Shaun of the Dead is a 2004 British horror comedy film directed by Edgar Wright. In a small flat on the outskirts of London, Shaun (Simon Pegg), a 30-something dull loser, must protect his ...more

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23
Zoolander is listed (or ranked) 23 on the list The Funniest Movies of the 2000s
Natalie Portman, Paris Hilton, Heidi Klum

Released: 2001

Directed by: Ben Stiller

Zoolander is a 2001 American comedy film directed by Ben Stiller and, starring Stiller and Owen Wilson. The film contains elements from a pair of short films directed by Russell Bates and ...more

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24
School of Rock is listed (or ranked) 24 on the list The Funniest Movies of the 2000s
WarrenMitchell added Sarah Silverman, Jack Black, Miranda Cosgrove

Released: 2003

Directed by: Richard Linklater

School of Rock is a 2003 American comedy film directed by Richard Linklater, written by Mike White, and starring Jack Black. The main plot follows struggling rock singer and guitarist, Dewey ...more

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25
Miss Congeniality is listed (or ranked) 25 on the list The Funniest Movies of the 2000s
Sandra Bullock, William Shatner, Michael Caine

Released: 2000

Directed by: Donald Petrie

Miss Congeniality is a 2000 comedy film directed by Donald Petrie, written by Marc Lawrence, Katie Ford and Caryn Lucas, starring Sandra Bullock, Michael Caine, Benjamin Bratt and Candice

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