Entertainment

The Funniest '90s Movies  

Ranker Film
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298.8k votes 13.7k voters 544k 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.

list ordered by
1
Office Space is listed (or ranked) 1 on the list The Funniest '90s Movies
Jennifer Aniston, John C. McGinley, 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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2
Groundhog Day is listed (or ranked) 2 on the list The Funniest '90s Movies
Bill Murray, Andie MacDowell, Michael Shannon
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

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#18 of 1,699 The Most Rewatchable Movies #54 of 410 The Best Rainy Day Movies #108 of 307 The Best Movies for Men

3
Dumb and Dumber is listed (or ranked) 3 on the list The Funniest '90s Movies
wiabux added Jim Carrey, Jeff Daniels, Teri Garr
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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#43 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #63 of 304 The Greatest Soundtracks of All Timefeaturing 'Dumb And Dumber' Is Far Darker And Creepier Than You Remember

4
Home Alone is listed (or ranked) 4 on the list The Funniest '90s Movies
Macaulay Culkin, Joe Pesci, John Candy
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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#23 of 630 The Greatest Guilty Pleasure Moviesfeaturing The Story Behind ‘Angels With Filthy Souls,’ The Fake Black-And-White Movie Inside ‘Home Alone’listed on The Highest Grossing 90s Movies

5
Austin Powers: Internati... is listed (or ranked) 5 on the list The Funniest '90s Movies
wiabux added Elizabeth Hurley, Will Ferrell, Carrie Fisher
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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#90 of 304 The Greatest Soundtracks of All Time #195 of 1,699 The Most Rewatchable Moviesfeaturing The Best Characters in the Austin Power Movies, Ranked

6
Happy Gilmore is listed (or ranked) 6 on the list The Funniest '90s Movies
Adam Sandler, Ben Stiller, Julie Bowen
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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#96 of 630 The Greatest Guilty Pleasure Moviesfeaturing 'Happy Gilmore' Is Secretly A Drama About Dealing With Loss And Grief The Best Quotes From 'Happy Gilmore' Are A Hole In One

7
Wayne's World is listed (or ranked) 7 on the list The Funniest '90s Movies
Alice Cooper, Mike Myers, Rob Lowe
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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8
Ace Ventura: Pet Detecti... is listed (or ranked) 8 on the list The Funniest '90s Movies
Jim Carrey, Courteney Cox, Dan Marino
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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#14 of 630 The Greatest Guilty Pleasure Movies #237 of 1,699 The Most Rewatchable Movies #26 of 1,204 The Absolute Funniest Movies Of All Time

9
Tommy Boy is listed (or ranked) 9 on the list The Funniest '90s Movies
Dan Aykroyd, Rob Lowe, Bo Derek
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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#72 of 630 The Greatest Guilty Pleasure Movies #216 of 1,699 The Most Rewatchable Movies #23 of 1,204 The Absolute Funniest Movies Of All Time

10
My Cousin Vinny is listed (or ranked) 10 on the list The Funniest '90s Movies
Marisa Tomei, Joe Pesci, Ralph Macchio
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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11
There's Something About ... is listed (or ranked) 11 on the list The Funniest '90s Movies
Cameron Diaz, Sarah Silverman, Ben Stiller
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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12
Mrs. Doubtfire is listed (or ranked) 12 on the list The Funniest '90s Movies
Robin Williams, Pierce Brosnan, Sally Field
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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#28 of 630 The Greatest Guilty Pleasure Moviesfeaturing Mrs. Doubtfire Is Actually A Dark Film About An Extremely Deranged Manlisted on Every Oscar Winning Film Ever

13
Liar Liar is listed (or ranked) 13 on the list The Funniest '90s Movies
wiabux added Jim Carrey, Jennifer Tilly, Krista Allen
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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#148 of 1,699 The Most Rewatchable Movies #59 of 1,204 The Absolute Funniest Movies Of All Timelisted on The Highest Grossing 90s Movies

14
American Pie is listed (or ranked) 14 on the list The Funniest '90s Movies
Alyson Hannigan, Tara Reid, Shannon Elizabeth
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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#60 of 304 The Greatest Soundtracks of All Time #114 of 571 Things That Are Not As Cool As People Think They Arefeaturing 'American Pie' Is A Nightmarish Vision Of Late '90s High School Life

15
The Wedding Singer is listed (or ranked) 15 on the list The Funniest '90s Movies
Drew Barrymore, Adam Sandler, Steve Buscemi
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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#222 of 1,699 The Most Rewatchable Movies #65 of 410 The Best Rainy Day Movies #68 of 1,204 The Absolute Funniest Movies Of All Time

16
Billy Madison is listed (or ranked) 16 on the list The Funniest '90s Movies
Adam Sandler, Steve Buscemi, Chris Farley
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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#238 of 1,699 The Most Rewatchable Movies #81 of 1,204 The Absolute Funniest Movies Of All Time #88 of 992 The All-Time Greatest Comedy Films

17
Big Daddy is listed (or ranked) 17 on the list The Funniest '90s Movies
laaaarrge added Adam Sandler, Jon Stewart, Steve Buscemi
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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#156 of 630 The Greatest Guilty Pleasure Movies #860 of 1,699 The Most Rewatchable Movieslisted on The Highest Grossing 90s Movies

18
The Waterboy is listed (or ranked) 18 on the list The Funniest '90s Movies
Adam Sandler, Kathy Bates, Rob Schneider
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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#57 of 630 The Greatest Guilty Pleasure Moviesfeaturing The Most Hilarious Quotes From 'The Waterboy'listed on The Highest Grossing 90s Movies

19
The Big Lebowski is listed (or ranked) 19 on the list The Funniest '90s Movies
Julianne Moore, Jeff Bridges, Tara Reid
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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20
Kingpin is listed (or ranked) 20 on the list The Funniest '90s Movies
wiabux added Bill Murray, Woody Harrelson, Randy Quaid
Kingpin is a 1996 American sport comedy film directed by the Farrelly brothers and starring Woody Harrelson, Randy Quaid, Vanessa Angel, and Bill Murray. It was filmed in and around Pittsburgh, ...more

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#1,092 of 1,699 The Most Rewatchable Movies #100 of 1,204 The Absolute Funniest Movies Of All Time #193 of 992 The All-Time Greatest Comedy Films

21
Austin Powers: The Spy W... is listed (or ranked) 21 on the list The Funniest '90s Movies
Elizabeth Hurley, Heather Graham, Will Ferrell
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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22
Robin Hood: Men in Tight... is listed (or ranked) 22 on the list The Funniest '90s Movies
Patrick Stewart, Mel Brooks, Dave Chappelle
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

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23
Rush Hour is listed (or ranked) 23 on the list The Funniest '90s Movies
wiabux added Jackie Chan, Roselyn Sánchez, Chris Tucker
Rush Hour is a 1998 American buddy action comedy film and the first installment in the Rush Hour series, directed by Brett Ratner and starring Jackie Chan and Chris Tucker. It was followed by ...more

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#54 of 630 The Greatest Guilty Pleasure Movies #537 of 1,699 The Most Rewatchable Movieslisted on The Highest Grossing 90s Movies

24
Toy Story is listed (or ranked) 24 on the list The Funniest '90s Movies
Tom Hanks, Tim Allen, Don Rickles
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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#2 of 600 The Best Animated Films Everfeaturing The Best Toy Story Characters in the Whole Series, Rankedlisted on The Highest Grossing 90s Movies

25
What About Bob? is listed (or ranked) 25 on the list The Funniest '90s Movies
Bill Murray, Richard Dreyfuss, Charlie Korsmo
What About Bob? is a 1991 comedy film directed by Frank Oz, and starring Bill Murray and Richard Dreyfuss. Murray plays Bob Wiley, a psychiatric patient who follows his egotistical psychiatrist ...more

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#118 of 630 The Greatest Guilty Pleasure Movies #529 of 1,699 The Most Rewatchable Movies #64 of 1,204 The Absolute Funniest Movies Of All Time