Entertainment

The Funniest '90s Movies  

Ranker Film
Originally by
291.6k votes 13.3k voters 526.1k 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 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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26
City Slickers is listed (or ranked) 26 on the list The Funniest '90s Movies
VanessaHawelu added 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
27
What About Bob? is listed (or ranked) 27 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
28
Men in Black is listed (or ranked) 28 on the list The Funniest '90s Movies
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
29
The Sandlot is listed (or ranked) 29 on the list The Funniest '90s Movies
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
30
Cool Runnings is listed (or ranked) 30 on the list The Funniest '90s Movies
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
31
Robin Hood: Men in Tights is listed (or ranked) 31 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
32
The Mask is listed (or ranked) 32 on the list The Funniest '90s Movies
VanessaHawelu added 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
33
Friday is listed (or ranked) 33 on the list The Funniest '90s Movies
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
34
Clueless is listed (or ranked) 34 on the list The Funniest '90s Movies
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
35
Dazed and Confused is listed (or ranked) 35 on the list The Funniest '90s Movies
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
36
Clerks is listed (or ranked) 36 on the list The Funniest '90s Movies
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
37
Beavis and Butt-head Do Americ... is listed (or ranked) 37 on the list The Funniest '90s Movies
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
38
Ace Ventura: When Nature Calls is listed (or ranked) 38 on the list The Funniest '90s Movies
wiabux added 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
39
The Nutty Professor is listed (or ranked) 39 on the list The Funniest '90s Movies
VanessaHawelu added Eddie Murphy, Jada Pinkett Smith, Dave Chappelle
The Nutty Professor is a 1996 American slapstick science-fiction comedy film directed by Tom Shadyac, and a remake of the 1963 film, which starred Jerry Lewis. Grossly overweight yet ...more
40
10 Things I Hate About You is listed (or ranked) 40 on the list The Funniest '90s Movies
VanessaHawelu added 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
41
Father of the Bride is listed (or ranked) 41 on the list The Funniest '90s Movies
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
42
A Night at the Roxbury is listed (or ranked) 42 on the list The Funniest '90s Movies
wiabux added 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
43
Dogma is listed (or ranked) 43 on the list The Funniest '90s Movies
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
44
Hot Shots! is listed (or ranked) 44 on the list The Funniest '90s Movies
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
45
The Mighty Ducks is listed (or ranked) 45 on the list The Funniest '90s Movies
VanessaHawelu added 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
46
Toy Story 2 is listed (or ranked) 46 on the list The Funniest '90s Movies
Tom Hanks, Kelsey Grammer, Tim Allen
Toy Story 2 is a 1999 American computer-animated comedy adventure film produced by Pixar Animation Studios and released by Walt Disney Pictures. Directed by John Lasseter and co-directed by Lee ...more
47
Major Payne is listed (or ranked) 47 on the list The Funniest '90s Movies
Damon Wayans, Karyn Parsons, Bam Bam Bigelow
Major Payne is a 1995 comedy film, starring Damon Wayans.
48
Half Baked is listed (or ranked) 48 on the list The Funniest '90s Movies
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
49
Galaxy Quest is listed (or ranked) 49 on the list The Funniest '90s Movies
wiabux added 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
50
Romy and Michele's High School... is listed (or ranked) 50 on the list The Funniest '90s Movies
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