comedy The Funniest '90s Movies  

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174.4k votes 7.7k voters 322.8k views 494 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 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 90 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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Office Space is listed (or ranked) 1 on the list The Funniest '90s Movies
Office Space 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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Groundhog Day is listed (or ranked) 2 on the list The Funniest '90s Movies
Groundhog Day 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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Dumb and Dumber is listed (or ranked) 3 on the list The Funniest '90s Movies
wiabux added Dumb and Dumber 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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Home Alone is listed (or ranked) 4 on the list The Funniest '90s Movies
Home Alone 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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Wayne's World is listed (or ranked) 5 on the list The Funniest '90s Movies
Wayne's World 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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Happy Gilmore is listed (or ranked) 6 on the list The Funniest '90s Movies
Happy Gilmore 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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Mrs. Doubtfire is listed (or ranked) 7 on the list The Funniest '90s Movies
Mrs. Doubtfire Robin Williams, Pierce Brosnan, Sally Field Mrs. Doubtfire is a 1993 American comedy film, starring Robin Williams and Sally Field and based on the novel Alias Madame Doubtfire by Anne Fine. It was directed by Chris Columbus and ...more

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There's Something About Mary is listed (or ranked) 8 on the list The Funniest '90s Movies
There's Something About Mary 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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American Pie is listed (or ranked) 9 on the list The Funniest '90s Movies
American Pie Alyson Hannigan, Tara Reid, Shannon Elizabeth American Pie is a 1999 teen sex 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 ...more

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Liar Liar is listed (or ranked) 10 on the list The Funniest '90s Movies
wiabux added Liar Liar 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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Austin Powers: International M... is listed (or ranked) 11 on the list The Funniest '90s Movies
wiabux added Austin Powers: International Man of Mystery 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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Ace Ventura: Pet Detective is listed (or ranked) 12 on the list The Funniest '90s Movies
Ace Ventura: Pet Detective 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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Tommy Boy is listed (or ranked) 13 on the list The Funniest '90s Movies
Tommy Boy 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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My Cousin Vinny is listed (or ranked) 14 on the list The Funniest '90s Movies
My Cousin Vinny 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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Big Daddy is listed (or ranked) 15 on the list The Funniest '90s Movies
laaaarrge added Big Daddy 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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The Wedding Singer is listed (or ranked) 16 on the list The Funniest '90s Movies
The Wedding Singer 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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Billy Madison is listed (or ranked) 17 on the list The Funniest '90s Movies
Billy Madison 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

The Best R-Rated Sex Comedies

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The Big Lebowski is listed (or ranked) 18 on the list The Funniest '90s Movies
The Big Lebowski Julianne Moore, Jeff Bridges, Tara Reid The Big Lebowski is a 1998 stoner crime comedy film written, produced, and directed by Joel and Ethan Coen. It stars Jeff Bridges as Jeffrey "The Dude" Lebowski, an unemployed Los ...more

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Rush Hour is listed (or ranked) 19 on the list The Funniest '90s Movies
wiabux added Rush Hour 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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The Waterboy is listed (or ranked) 20 on the list The Funniest '90s Movies
The Waterboy 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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Clueless is listed (or ranked) 21 on the list The Funniest '90s Movies
Clueless Alicia Silverstone, Brittany Murphy, Paul Rudd 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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Kingpin is listed (or ranked) 22 on the list The Funniest '90s Movies
wiabux added Kingpin 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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Friday is listed (or ranked) 23 on the list The Funniest '90s Movies
Friday Ice Cube, Meagan Good, Nia Long 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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What About Bob? is listed (or ranked) 24 on the list The Funniest '90s Movies
What About Bob? 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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Toy Story is listed (or ranked) 25 on the list The Funniest '90s Movies
Toy Story 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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Men in Black is listed (or ranked) 26 on the list The Funniest '90s Movies
Men in Black Will Smith, Sylvester Stallone, Steven Spielberg 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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The Sandlot is listed (or ranked) 27 on the list The Funniest '90s Movies
The Sandlot James Earl Jones, Denis Leary, Karen Allen 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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Austin Powers: The Spy Who Sha... is listed (or ranked) 28 on the list The Funniest '90s Movies
Austin Powers: The Spy Who Shagged Me 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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South Park: Bigger, Longer & U... is listed (or ranked) 29 on the list The Funniest '90s Movies
South Park: Bigger, Longer & Uncut George Clooney, Minnie Driver, Isaac Hayes South Park: Bigger, Longer & Uncut is a 1999 American adult animated satirical musical comedy film based on the animated television series South Park, and produced, co-written by and ...more

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The Mask is listed (or ranked) 30 on the list The Funniest '90s Movies
VanessaHawelu added The Mask Cameron Diaz, Jim Carrey, Ben Stein The Mask is a 1994 American fantasy slapstick action comedy film based on a series of comic books published by Dark Horse Comics. This film was directed by Chuck Russell, and produced by Dark ...more

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Robin Hood: Men in Tights is listed (or ranked) 31 on the list The Funniest '90s Movies
Robin Hood: Men in Tights 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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Dazed and Confused is listed (or ranked) 32 on the list The Funniest '90s Movies
Dazed and Confused Ben Affleck, Milla Jovovich, Matthew McConaughey Dazed and Confused is a 1993 coming of age comedy film written and directed by Richard Linklater. The film features a large ensemble cast of actors who would later become stars, including ...more

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City Slickers is listed (or ranked) 33 on the list The Funniest '90s Movies
VanessaHawelu added City Slickers Jake Gyllenhaal, Billy Crystal, Danielle Harris City Slickers is a 1991 American western comedy film directed by Ron Underwood and starring Billy Crystal, Daniel Stern, Bruno Kirby and Jack Palance, with supporting roles by Patricia Wettig, ...more

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Ace Ventura: When Nature Calls is listed (or ranked) 34 on the list The Funniest '90s Movies
wiabux added Ace Ventura: When Nature Calls Jim Carrey, Sophie Okonedo, Adewale Akinnuoye-Agbaje Ace Ventura: When Nature Calls is a 1995 American film and the sequel to the 1994 American film Ace Ventura: Pet Detective. Jim Carrey reprises his role as the title character Ace Ventura, a ...more

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Kindergarten Cop is listed (or ranked) 35 on the list The Funniest '90s Movies
VanessaHawelu added Kindergarten Cop Arnold Schwarzenegger, Odette Annable, Angela Bassett Kindergarten Cop is a 1990 American comedy film directed by Ivan Reitman and starring Arnold Schwarzenegger as John Kimble, a tough police detective, who must go undercover and pose as a ...more

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Cool Runnings is listed (or ranked) 36 on the list The Funniest '90s Movies
Cool Runnings John Candy, Malik Yoba, Jay Brazeau Cool Runnings is a 1993 American sports film directed by Jon Turteltaub, and starring Leon, Doug E. Doug, Rawle D. Lewis, Malik Yoba and John Candy. The film was released in the United States on ...more

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Dogma is listed (or ranked) 37 on the list The Funniest '90s Movies
Dogma Ben Affleck, Matt Damon, Chris Rock Dogma is a 1999 American comedy film, written and directed by Kevin Smith, who also stars along with Ben Affleck, Matt Damon, Linda Fiorentino, Alan Rickman, Bud Cort, Salma Hayek, Chris Rock, ...more

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The Nutty Professor is listed (or ranked) 38 on the list The Funniest '90s Movies
VanessaHawelu added The Nutty Professor Eddie Murphy, Jada Pinkett Smith, Dave Chappelle The Nutty Professor is a 1996 American science fiction comedy film starring Eddie Murphy. It is a remake of the 1963 film of the same name, which starred Jerry Lewis, and was itself based on ...more

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Galaxy Quest is listed (or ranked) 39 on the list The Funniest '90s Movies
wiabux added Galaxy Quest Sigourney Weaver, Alan Rickman, Tim Allen Galaxy Quest is a 1999 American science fiction action comedy film directed by Dean Parisot and written by David Howard and Robert Gordon. The film follows the adventures of a troupe of actors ...more

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Beavis and Butt-head Do Americ... is listed (or ranked) 40 on the list The Funniest '90s Movies
Beavis and Butt-head Do America Demi Moore, Bruce Willis, David Letterman Beavis and Butt-head Do America is a 1996 American animated road comedy film, based on the TV series Beavis and Butt-head. It was produced by Paramount Pictures in association with Geffen ...more

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Half Baked is listed (or ranked) 41 on the list The Funniest '90s Movies
Half Baked Snoop Dogg, Jon Stewart, Willie Nelson Half Baked is a 1998 American stoner comedy film starring Dave Chappelle, Jim Breuer, Harland Williams and Guillermo Díaz. The film was directed by Tamra Davis, co-written by Chappelle ...more

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Romy and Michele's High School... is listed (or ranked) 42 on the list The Funniest '90s Movies
Romy and Michele's High School Reunion Lisa Kudrow, Janeane Garofalo, Mira Sorvino Romy and Michele's High School Reunion is a 1997 comedy film starring Lisa Kudrow, Mira Sorvino, Janeane Garofalo, Camryn Manheim, and Alan Cumming directed by David Mirkin. The plot revolves ...more

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A Night at the Roxbury is listed (or ranked) 43 on the list The Funniest '90s Movies
wiabux added A Night at the Roxbury Eva Mendes, Will Ferrell, Jennifer Coolidge A Night at the Roxbury is a 1998 American comedy film based on a recurring skit on television's long-running Saturday Night Live called "The Roxbury Guys". Saturday Night Live regulars ...more

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Don't Be a Menace to South Cen... is listed (or ranked) 44 on the list The Funniest '90s Movies
VanessaHawelu added Don't Be a Menace to South Central While Drinking Your Juice in the Hood Vivica A. Fox, Bernie Mac, Damon Wayans Don't Be a Menace to South Central While Drinking Your Juice in the Hood is a 1996 American comedy film directed by Paris Barclay, and produced by Keenen Ivory Wayans, and also written by Wayans ...more

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The Mighty Ducks is listed (or ranked) 45 on the list The Funniest '90s Movies
VanessaHawelu added The Mighty Ducks Joshua Jackson, Emilio Estevez, Dan Tamberelli The Mighty Ducks is a 1992 American sports comedy film directed by Stephen Herek, starring Emilio Estevez. It was produced by Avnet–Kerner Productions and distributed by Walt Disney Pictures. It ...more

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Addams Family Values is listed (or ranked) 46 on the list The Funniest '90s Movies
VanessaHawelu added Addams Family Values Christina Ricci, Christopher Lloyd, Anjelica Huston Addams Family Values is a 1993 American dark comedy film, which is the sequel to the 1991 American film The Addams Family. It was written by Paul Rudnick and directed by Barry Sonnenfeld, and ...more

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Hot Shots! is listed (or ranked) 47 on the list The Funniest '90s Movies
Hot Shots! Charlie Sheen, Kristy Swanson, Valeria Golino Hot Shots! is a 1991 comedy spoof film starring Charlie Sheen, Cary Elwes, Valeria Golino, Lloyd Bridges, Kevin Dunn, Jon Cryer and Ryan Stiles. It was directed by Jim Abrahams, and was written ...more

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10 Things I Hate About You is listed (or ranked) 48 on the list The Funniest '90s Movies
VanessaHawelu added 10 Things I Hate About You Joseph Gordon-Levitt, Gabrielle Union, Heath Ledger 10 Things I Hate About You is a 1999 American teen romantic comedy-drama film. It is directed by Gil Junger and stars Julia Stiles, Heath Ledger and Joseph Gordon-Levitt. The romantic comedy ...more

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Clerks is listed (or ranked) 49 on the list The Funniest '90s Movies
Clerks Kevin Smith, Jason Mewes, Scott Mosier Clerks is a 1994 American black-and-white comedy film written and directed by Kevin Smith, who also appears in the film as Silent Bob. Starring Brian O'Halloran as Dante Hicks and Jeff Anderson ...more

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Father of the Bride is listed (or ranked) 50 on the list The Funniest '90s Movies
Father of the Bride Steve Martin, Diane Keaton, Martin Short Father of the Bride is a 1991 American comedy film starring Steve Martin, Diane Keaton, Kimberly Williams, George Newbern, Martin Short, B.D. Wong and Kieran Culkin. It is a remake of the 1950 ...more