Entertainment

The Funniest Movies of the 2000s 

Ranker Film
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Updated November 7, 2019 97.7k votes 6.1k voters 209.8k views 125 items

List Rules Top comedies and dramatic comedy films released between January 2000 and December 2009

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.

list ordered by
1
Superbad is listed (or ranked) 1 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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#25 of 1,009 The All-Time Greatest Comedy Films #13 of 1,196 The Absolute Funniest Movies Of All Time Behind-The-Scenes Stories From The Making Of 'Superbad'

2
Step Brothers is listed (or ranked) 2 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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#28 of 1,009 The All-Time Greatest Comedy Films #46 of 107 The Funniest Movies Starring SNL Cast Members

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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#213 of 1,699 The Most Rewatchable Movies #5 of 1,009 The All-Time Greatest Comedy Films

4
The Hangover is listed (or ranked) 4 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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#95 of 1,699 The Most Rewatchable Movies #3 of 1,196 The Absolute Funniest Movies Of All Time

5
DodgeBall: A True Underd... is listed (or ranked) 5 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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#48 of 1,009 The All-Time Greatest Comedy Films #54 of 1,196 The Absolute Funniest Movies Of All Time

6
Wedding Crashers is listed (or ranked) 6 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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7
The 40-Year-Old Virgin ... is listed (or ranked) 7 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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8
Old School is listed (or ranked) 8 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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#36 of 1,009 The All-Time Greatest Comedy Films #51 of 116 Movies That Need Sequels

9
Elf is listed (or ranked) 9 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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10
Tropic Thunder is listed (or ranked) 10 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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#844 of 1,699 The Most Rewatchable Movies #65 of 1,009 The All-Time Greatest Comedy Films #57 of 1,196 The Absolute Funniest Movies Of All Time

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
Mean Girls is listed (or ranked) 12 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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#2 of 803 The Greatest Chick Flicks Ever Made #253 of 1,196 The Absolute Funniest Movies Of All Time Behind-The-Scenes Secrets Of 'Mean Girls'

13
Meet the Parents is listed (or ranked) 13 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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14
Napoleon Dynamite is listed (or ranked) 14 on the list The Funniest Movies of the 2000s
looksharp added Haylie Duff, Jon Heder, Diedrich Bader

Released: 2004

Directed by: Jared Hess

Napoleon Dynamite is a 2004 American independent art-house comedy film written by Jared and Jerusha Hess and directed by Jared. The film stars Jon Heder in the role of the title character, for ...more

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#239 of 1,699 The Most Rewatchable Movies #49 of 1,009 The All-Time Greatest Comedy Films #44 of 1,196 The Absolute Funniest Movies Of All Time

15
School of Rock is listed (or ranked) 15 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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16
Knocked Up is listed (or ranked) 16 on the list The Funniest Movies of the 2000s
Jessica Alba, Eva Mendes, Katherine Heigl

Released: 2007

Directed by: Judd Apatow

Knocked Up is a 2007 American romantic comedy film co-produced, written, and directed by Judd Apatow. The films stars Seth Rogen, Katherine Heigl, Paul Rudd, and Leslie Mann. It follows the ...more

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17
Zoolander is listed (or ranked) 17 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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18
Bruce Almighty is listed (or ranked) 18 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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#85 of 1,009 The All-Time Greatest Comedy Films #100 of 165 Live Action Films with the Best CGI Effects #26 of 100 The Most Rewatchable Comedy Movies

19
The Other Guys is listed (or ranked) 19 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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20
Shrek 2 is listed (or ranked) 20 on the list The Funniest Movies of the 2000s
but chickens double d added Cameron Diaz, Eddie Murphy, Joan Rivers

Released: 2004

Directed by: Kelly Asbury, Andrew Adamson, Conrad Vernon

Shrek 2 is a 2004 American computer-animated, comedy film directed by Andrew Adamson, Kelly Asbury, and Conrad Vernon. It is the sequel to 2001's Shrek and the second installment in the series. ...more

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21
Monsters, Inc. is listed (or ranked) 21 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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22
Pineapple Express is listed (or ranked) 22 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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23
Hot Fuzz is listed (or ranked) 23 on the list The Funniest Movies of the 2000s
wiabux added Cate Blanchett, Martin Freeman, Simon Pegg

Released: 2007

Directed by: Edgar Wright

Hot Fuzz is a 2007 British action comedy parody film directed by Edgar Wright, written by Wright and Simon Pegg, and starring Pegg and Nick Frost. The film follows two police officers attempting ...more

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#395 of 1,699 The Most Rewatchable Movies #128 of 1,009 The All-Time Greatest Comedy Films

24
Shaun of the Dead is listed (or ranked) 24 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 and written by Wright and Simon Pegg, and starring Pegg and Nick Frost. Pegg plays Shaun, a man attempting to get ...more

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#97 of 1,699 The Most Rewatchable Movies #32 of 1,196 The Absolute Funniest Movies Of All Time

25
50 First Dates is listed (or ranked) 25 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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#162 of 1,699 The Most Rewatchable Movies #162 of 1,009 The All-Time Greatest Comedy Films 50 First Dates Isn't Romantic - It's About A Guy Who Takes Advantage Of A Disabled Woman