watchworthy presents

The Funniest '90s Movies 

Ranker Film
Originally by
Updated March 18, 2020 305.8k votes 14.1k voters 560.6k views 493 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.

Data-driven recommendations based on voting from over 40 million monthly visits to Ranker. Try the free app
list ordered by
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

More Happy Gilmore 

#101 of 1,699 The Most Rewatchable Movies 'Happy Gilmore' Is Secretly A Drama About Dealing With Loss And Grief The Best Quotes From 'Happy Gilmore' Are A Hole In One

2
Ace Ventura: Pet Detecti... is listed (or ranked) 2 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

More Ace Ventura: Pet Detective 

#30 of 1,017 The All-Time Greatest Comedy Films #160 of 548 The Greatest Movies for Guys

3
Dumb and Dumber is listed (or ranked) 3 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

More Dumb and Dumber 

#156 of 1,699 The Most Rewatchable Movies 'Dumb And Dumber' Is Far Darker And Creepier Than You Remember

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

More Tommy Boy 

#182 of 1,699 The Most Rewatchable Movies #17 of 1,017 The All-Time Greatest Comedy Films #132 of 548 The Greatest Movies for Guys

5
Billy Madison is listed (or ranked) 5 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

More Billy Madison 

#354 of 599 The Greatest Epic Movies Ever Made #89 of 1,017 The All-Time Greatest Comedy Films

6
The Waterboy is listed (or ranked) 6 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

More The Waterboy 

#94 of 1,017 The All-Time Greatest Comedy Films The Most Hilarious Quotes From 'The Waterboy'listed on The 50 Highest Grossing '90s Movies, Ranked

7
There's Something About ... is listed (or ranked) 7 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

More There's Something About Mary 

#360 of 1,699 The Most Rewatchable Movies Behind-The-Scenes Stories From The Making Of ‘There’s Something About Mary’listed on The 50 Highest Grossing '90s Movies, Ranked

8
Men in Black is listed (or ranked) 8 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

More Men in Black 

#7 of 190 The Best Alien Movies Ever Made #497 of 721 The Best Black Movies Ever Made, Rankedlisted on Every Oscar Winning Film Ever

9
Mrs. Doubtfire is listed (or ranked) 9 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

More Mrs. Doubtfire 

#71 of 1,699 The Most Rewatchable Movies Mrs. Doubtfire Is Actually A Dark Film About An Extremely Deranged Manlisted on Every Oscar Winning Film Ever

10
Friday is listed (or ranked) 10 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
11
Wayne's World is listed (or ranked) 11 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

More Wayne's World 

#153 of 1,699 The Most Rewatchable Movies #24 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime Why Did It Take 20 Years For Dana Carvey To Forgive Mike Myers?

12
The Sandlot is listed (or ranked) 12 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

More The Sandlot 

#87 of 1,699 The Most Rewatchable Movies #36 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime What Ever Happened To All The Kids From The Sandlot?

13
Austin Powers: Internati... is listed (or ranked) 13 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

More Austin Powers: International Man of Mystery 

#195 of 1,699 The Most Rewatchable Movies #89 of 302 The Greatest Soundtracks of All Time The Best Characters in the Austin Power Movies, Ranked

14
Toy Story is listed (or ranked) 14 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

More Toy Story 

#2 of 598 The Best Animated Films Ever The Best Toy Story Characters in the Whole Series, Rankedlisted on The 50 Highest Grossing '90s Movies, Ranked

15
The Wedding Singer is listed (or ranked) 15 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
16
Liar Liar is listed (or ranked) 16 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

More Liar Liar 

#60 of 1,199 The Absolute Funniest Movies Of All Timelisted on The 50 Highest Grossing '90s Movies, Ranked

17
American Pie is listed (or ranked) 17 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

More American Pie 

#272 of 1,699 The Most Rewatchable Movies #330 of 599 The Greatest Epic Movies Ever Made 'American Pie' Is A Nightmarish Vision Of Late '90s High School Life

18
My Cousin Vinny is listed (or ranked) 18 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

More My Cousin Vinny 

#116 of 1,699 The Most Rewatchable Movies Behind-The-Scenes Stories From 'My Cousin Vinny'listed on Every Oscar Winning Film Ever

19
Groundhog Day is listed (or ranked) 19 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, starring Bill Murray, Andie MacDowell, and Chris Elliott. It was written by Ramis and Danny Rubin, based on a story ...more

More Groundhog Day 

#18 of 1,699 The Most Rewatchable Movies #54 of 410 The Best Rainy Day Movies

20
The Big Lebowski is listed (or ranked) 20 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

More The Big Lebowski 

#114 of 1,699 The Most Rewatchable Movies 20 Things You Didn't Know About The Big Lebowski 'The Big Lebowski' Fan Theories That Really Tie The Film Together

21
Home Alone is listed (or ranked) 21 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

More Home Alone 

#5 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime All The Traps In Home Alone and Home Alone 2, Ranked By Horrific Brutalitylisted on The 50 Highest Grossing '90s Movies, Ranked

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

More Clueless 

#121 of 1,699 The Most Rewatchable Movies #54 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime The Best Outfits from Clueless

23
Big Daddy is listed (or ranked) 23 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

More Big Daddy 

#157 of 624 The Greatest Guilty Pleasure Movieslisted on The 50 Highest Grossing '90s Movies, Ranked

24
Robin Hood: Men in Tight... is listed (or ranked) 24 on the list The Funniest '90s Movies
Patrick Stewart, Mel Brooks, Dave Chappelle

Released: 1993

Directed by: Mel Brooks

Robin Hood: Men in Tights is a 1993 French-American musical adventure comedy film and a parody of the Robin Hood story. Produced and directed by Mel Brooks, the film stars Cary Elwes, Richard ...more

More Robin Hood: Men in Tights 

#119 of 1,699 The Most Rewatchable Movies Here's What The Cast Of Robin Hood: Men In Tights Looks Like Now

25
Austin Powers: The Spy W... is listed (or ranked) 25 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

More Austin Powers: The Spy Who Shagged Me 

#80 of 1,199 The Absolute Funniest Movies Of All Time The Best Characters in the Austin Power Movies, Rankedlisted on The 50 Highest Grossing '90s Movies, Ranked