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The Funniest '90s Movies 

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Updated April 17, 2020 315.5k votes 14.7k voters 589.9k views 373 items

List Rules Comedies and comedy films released between 1990 and 1999

List of the funniest 90s movies. The best comedies of the 1990s make up the titles on this ranking page. Nineties nostalgia exists for a reason. One of the main reasons is the unforgettable  and classic comedies that came out in movie theaters. It is also why we still constantly replay them in our homes today. Thanks to the Zucker brothers, we got the Farrelly brothers (and thereby There's Something About Mary) while the Cohen Brothers furthered their epic 80s comedy filmography with The Big Lebowski. Adam Sandler became one of the richest actors in all of Hollywood history as a result of the 1990s. In fact, his popular '90s comedy movies Billy Madison and Happy Gilmore make up his production company name today: Happy Madison. And who can forget Austin Powers' catchphrases spreading like wildfire? Kevin Smith also had two slam dunks with Clerks and Dogma, while the David Spade-Chris Farley funny, unforgettable, onscreen duo did the same with Black Sheep and Tommy Boy.

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1
Happy Gilmore is listed (or ranked) 1 on the list The Funniest '90s Movies
Adam Sandler, Ben Stiller, Julie Bowen

Released: 1996

Directed by: Dennis Dugan

Happy Gilmore is a 1996 sports comedy film directed by Dennis Dugan and produced by Robert Simonds. It stars Adam Sandler as the title character, an unsuccessful ice hockey player who discovers ...more

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2
Dumb and Dumber is listed (or ranked) 2 on the list The Funniest '90s Movies
wiabux added Jim Carrey, Jeff Daniels, Teri Garr

Released: 1994

Directed by: Peter Farrelly, Bobby Farrelly

Dumb and Dumber is a 1994 American road buddy comedy film starring Jim Carrey and Jeff Daniels. It was written by the Farrelly brothers and Bennett Yellin, and is the Farrelly Brothers ...more

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'Dumb And Dumber' Is Far Darker And Creepier Than You Remember #94 of 299 The Greatest Soundtracks of All Time #136 of 1,646 The Most Rewatchable Movies

3
Ace Ventura: Pet Detecti... is listed (or ranked) 3 on the list The Funniest '90s Movies
Jim Carrey, Courteney Cox, Dan Marino

Released: 1994

Directed by: Tom Shadyac

Ace Ventura: Pet Detective is a 1994 American comedy detective film directed by Tom Shadyac, and co-written by and starring Jim Carrey. It was developed by the film's original writer, Jack ...more

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#234 of 1,646 The Most Rewatchable Movies #75 of 133 Movies That Should Never Be Remade #20 of 560 The Greatest Guilty Pleasure Movies

4
Tommy Boy is listed (or ranked) 4 on the list The Funniest '90s Movies
Dan Aykroyd, Rob Lowe, Bo Derek

Released: 1995

Directed by: Peter Segal

Tommy Boy is a 1995 American road comedy film directed by Peter Segal, written by Bonnie and Terry Turner, produced by Lorne Michaels, and starring former Saturday Night Live castmates and close ...more

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The Most Hilarious 'Tommy Boy' Quotes #210 of 1,646 The Most Rewatchable Movies #72 of 133 Movies That Should Never Be Remade

5
There's Something About ... is listed (or ranked) 5 on the list The Funniest '90s Movies
Cameron Diaz, Sarah Silverman, Ben Stiller

Released: 1998

Directed by: Peter Farrelly, Bobby Farrelly

There's Something About Mary is a 1998 comedy film, directed by the Farrelly brothers, Bobby and Peter. It stars Cameron Diaz, Matt Dillon and Ben Stiller, and it is a combination of romantic ...more

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Behind-The-Scenes Stories From The Making Of ‘There’s Something About Mary’ #87 of 299 The Greatest Soundtracks of All Timelisted on The 50 Highest Grossing '90s Movies, Ranked

6
Austin Powers: Internati... is listed (or ranked) 6 on the list The Funniest '90s Movies
wiabux added Elizabeth Hurley, Will Ferrell, Carrie Fisher

Released: 1997

Directed by: Jay Roach

Austin Powers: International Man of Mystery is a 1997 American action comedy film and the first installment of the Austin Powers series. It was directed by Jay Roach and written by Mike Myers, ...more

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The Best Characters in the Austin Power Movies, Ranked #60 of 299 The Greatest Soundtracks of All Time #193 of 1,646 The Most Rewatchable Movies

7
The Wedding Singer is listed (or ranked) 7 on the list The Funniest '90s Movies
Drew Barrymore, Adam Sandler, Steve Buscemi

Released: 1998

Directed by: Frank Coraci

The Wedding Singer is a 1998 romantic comedy film written by Tim Herlihy and directed by Frank Coraci. It stars Adam Sandler as a wedding singer in the 1980s and Drew Barrymore as a waitress ...more

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8
Groundhog Day is listed (or ranked) 8 on the list The Funniest '90s Movies
Bill Murray, Andie MacDowell, Michael Shannon

Released: 1993

Directed by: Harold Ramis

Groundhog Day is a 1993 American fantasy comedy film directed by Harold Ramis. A derisive weatherman (Bill Murray) finds himself reliving the same day over and over again after reporting a small ...more

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#70 of 355 The Best Rainy Day Movies #41 of 1,646 The Most Rewatchable Movies #33 of 133 Movies That Should Never Be Remade

9
The Waterboy is listed (or ranked) 9 on the list The Funniest '90s Movies
Adam Sandler, Kathy Bates, Rob Schneider

Released: 1998

Directed by: Frank Coraci

The Waterboy is a 1998 American sports/comedy film directed by Frank Coraci, starring Adam Sandler, Kathy Bates, Fairuza Balk, Henry Winkler, Jerry Reed, Larry Gilliard, Jr., Blake Clark, Peter ...more

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The Most Hilarious Quotes From 'The Waterboy' #39 of 560 The Greatest Guilty Pleasure Movieslisted on The 50 Highest Grossing '90s Movies, Ranked

10
Billy Madison is listed (or ranked) 10 on the list The Funniest '90s Movies
Adam Sandler, Steve Buscemi, Chris Farley

Released: 1995

Directed by: Tamra Davis

Billy Madison is a 1995 American family comedy film directed by Tamra Davis. It stars Adam Sandler in the title role, along with Bradley Whitford, Bridgette Wilson, Norm Macdonald, and Darren ...more

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#239 of 1,646 The Most Rewatchable Movies #96 of 1,138 The Absolute Funniest Movies Of All Time #168 of 923 The All-Time Greatest Comedy Films

11
Friday is listed (or ranked) 11 on the list The Funniest '90s Movies
Ice Cube, Meagan Good, Nia Long

Released: 1995

Directed by: F. Gary Gray

Friday is a 1995 American stoner buddy comedy film directed by F. Gary Gray in his directorial debut, and starring Ice Cube, Chris Tucker, Nia Long, Bernie Mac, Tiny 'Zeus' Lister Jr, and John ...more

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#146 of 299 The Greatest Soundtracks of All Time #359 of 1,646 The Most Rewatchable Movies #76 of 1,138 The Absolute Funniest Movies Of All Time

12
My Cousin Vinny is listed (or ranked) 12 on the list The Funniest '90s Movies
Marisa Tomei, Joe Pesci, Ralph Macchio

Released: 1992

Directed by: Jonathan Lynn

My Cousin Vinny is a 1992 American comedy film written by Dale Launer and directed by Jonathan Lynn. The film stars Joe Pesci, Ralph Macchio, Marisa Tomei, Mitchell Whitfield, Lane Smith, Bruce ...more

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Behind-The-Scenes Stories From 'My Cousin Vinny' #112 of 1,646 The Most Rewatchable Movieslisted on Every Oscar Winning Film Ever

13
Wayne's World is listed (or ranked) 13 on the list The Funniest '90s Movies
Alice Cooper, Mike Myers, Rob Lowe

Released: 1992

Directed by: Penelope Spheeris

Wayne's World is a 1992 American comedy film directed by Penelope Spheeris and starring Mike Myers as Wayne Campbell and Dana Carvey as Garth Algar, hosts of the Aurora, Illinois-based ...more

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Behind The Scenes Of The 'Wayne’s World' Version Of 'Bohemian Rhapsody' #148 of 1,646 The Most Rewatchable Movies #53 of 133 Movies That Should Never Be Remade

14
Liar Liar is listed (or ranked) 14 on the list The Funniest '90s Movies
wiabux added Jim Carrey, Jennifer Tilly, Krista Allen

Released: 1997

Directed by: Tom Shadyac

Liar Liar is a 1997 American comedy film written by Paul Guay and Stephen Mazur, directed by Tom Shadyac and starring Jim Carrey who was nominated for a Golden Globe Award for Best Performance ...more

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#140 of 1,646 The Most Rewatchable Movies #46 of 1,138 The Absolute Funniest Movies Of All Timelisted on The 50 Highest Grossing '90s Movies, Ranked

15
Mrs. Doubtfire is listed (or ranked) 15 on the list The Funniest '90s Movies
Robin Williams, Pierce Brosnan, Sally Field

Released: 1993

Directed by: Chris Columbus, Chuck Jones

Mrs. Doubtfire is a 1993 American comedy-drama film directed by Chris Columbus, based on the novel Alias Madame Doubtfire by Anne Fine. A recently divorced actor (Robin Williams) decides to ...more

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Mrs. Doubtfire Is Actually A Dark Film About An Extremely Deranged Man #57 of 1,646 The Most Rewatchable Movieslisted on Every Oscar Winning Film Ever

16
American Pie is listed (or ranked) 16 on the list The Funniest '90s Movies
Alyson Hannigan, Tara Reid, Shannon Elizabeth

Released: 1999

Directed by: Chris Weitz, Paul Weitz

American Pie is a 1999 teen comedy film written by Adam Herz and directed by brothers Paul and Chris Weitz, in their directorial film debut. It is the first film in the American Pie theatrical ...more

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'American Pie' Is A Nightmarish Vision Of Late '90s High School Life #108 of 299 The Greatest Soundtracks of All Time #290 of 1,646 The Most Rewatchable Movies

17
Home Alone is listed (or ranked) 17 on the list The Funniest '90s Movies
Macaulay Culkin, Joe Pesci, John Candy

Released: 1990

Directed by: Chris Columbus

Home Alone is a 1990 American Christmas family comedy film written and produced by John Hughes and directed by Chris Columbus. The film stars Macaulay Culkin as Kevin McCallister, a boy who is ...more

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18
The Sandlot is listed (or ranked) 18 on the list The Funniest '90s Movies
James Earl Jones, Denis Leary, Karen Allen

Released: 1993

Directed by: David M. Evans

The Sandlot, also known as The Sandlot Kids, is a 1993 American coming-of-age film Comedy directed by David M. Evans, which tells the story of a group of young baseball players during the summer ...more

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19
Men in Black is listed (or ranked) 19 on the list The Funniest '90s Movies
Will Smith, Sylvester Stallone, Steven Spielberg

Released: 1997

Directed by: Barry Sonnenfeld

Men in Black is a 1997 American science fiction action comedy film directed by Barry Sonnenfeld, produced by Walter F. Parkes and Laurie MacDonald and starring Tommy Lee Jones and Will Smith. ...more

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#98 of 299 The Greatest Soundtracks of All Time #182 of 355 The Best Rainy Day Movieslisted on Every Oscar Winning Film Ever

20
Toy Story is listed (or ranked) 20 on the list The Funniest '90s Movies
Tom Hanks, Tim Allen, Don Rickles

Released: 1995

Directed by: John Lasseter

Toy Story is a 1995 American computer-animated buddy-comedy adventure film produced by Pixar Animation Studios and released by Walt Disney Pictures. Directed by John Lasseter, Toy Story was the ...more

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21
The Big Lebowski is listed (or ranked) 21 on the list The Funniest '90s Movies
Julianne Moore, Jeff Bridges, Tara Reid

Released: 1998

Directed by: Ethan Coen, Joel Coen

The Big Lebowski is a 1998 stoner comedy film written, produced, and directed by Joel and Ethan Coen. It stars Jeff Bridges as Jeffrey "The Dude" Lebowski, an unemployed Los Angeles ...more

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22
Clueless is listed (or ranked) 22 on the list The Funniest '90s Movies
Alicia Silverstone, Brittany Murphy, Paul Rudd

Released: 1995

Directed by: Amy Heckerling

Clueless is a 1995 American comedy film loosely based on Jane Austen's 1815 novel Emma. It stars Alicia Silverstone, Stacey Dash, Paul Rudd, and Brittany Murphy. The film is set in Beverly Hills ...more

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The Best Outfits from Clueless #30 of 299 The Greatest Soundtracks of All Time #21 of 355 The Best Rainy Day Movies

23
Office Space is listed (or ranked) 23 on the list The Funniest '90s Movies
Jennifer Aniston, John C. McGinley, Mike Judge

Released: 1999

Directed by: Mike Judge

Office Space is a 1999 American comedy film written and directed by Mike Judge. The film satirizes the everyday work life of a typical mid-to-late-1990s software company, it focuses on a handful ...more

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#325 of 355 The Best Rainy Day Movies #117 of 1,646 The Most Rewatchable Movieslisted on The Very Best Movies About Hackers

24
Austin Powers: The Spy W... is listed (or ranked) 24 on the list The Funniest '90s Movies
Elizabeth Hurley, Heather Graham, Will Ferrell

Released: 1999

Directed by: Jay Roach

Austin Powers: The Spy Who Shagged Me is a 1999 action comedy film and the second film in the Austin Powers series. It is preceded by the original film, Austin Powers: International Man of ...more

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The Best Characters in the Austin Power Movies, Ranked #43 of 299 The Greatest Soundtracks of All Timelisted on The 50 Highest Grossing '90s Movies, Ranked

25
Big Daddy is listed (or ranked) 25 on the list The Funniest '90s Movies
laaaarrge added Adam Sandler, Jon Stewart, Steve Buscemi

Released: 1999

Directed by: Dennis Dugan

Big Daddy is a 1999 American comedy film directed by Dennis Dugan and starring Adam Sandler. The film was produced by Robert Simonds and released on June 25, 1999, by Columbia Pictures where it ...more

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#329 of 1,646 The Most Rewatchable Movies #157 of 560 The Greatest Guilty Pleasure Movieslisted on The 50 Highest Grossing '90s Movies, Ranked