75 Best Comedies of the 1990s

April 26, 2018 by Steven M. Peters

Source: Courtesy of Walt Disney Studios Motion Pictures
Though comedy films of the 1990s may seem like they were strictly vehicles for comedians such as Adam Sandler, Ben Stiller, and Mike Myers, the decade offered much more. The comedy genre, even in the 1990s, has always been very diverse.

As was the case with American cinema in general, the advent of small-budget, independent films in the 1990s helped push comedy movies in a more creative direction, as filmmakers were more willing to take risks with their work. The result was a decade of movies vastly differing in their creative approach but sharing one important ingredient – a good sense of humor.

24/7 Wall St. determined the best comedies of the decade by creating an index based on user ratings from the Internet Movie Database and Rotten Tomatoes.

Click here to see the 75 best comedies of the 1990s.
Click here to see our methodology.

As is the case with Hollywood in every decade, there were a number of hugely successful, big budget comedy movies in the 1990s. Columbia Pictures’ “Men in Black” and Walt Disney Studios’ “Toy Story 2” each cost $90 million to produce and grossed over $245 million in the U.S. alone.

While even successful comedies didn’t gross quite as much as other Hollywood blockbusters in other genres of the 1990s, the decade is notable for the number of independently produced, memorable micro-budget films. Among titles on our list are “Bottle Rocket,” “Slacker,” and “Clerks.” As our list is based on audience and critic ratings, the inclusion of such movies demonstrates that moviegoers often prefer smaller indie fare to huge Hollywood productions.

The directors of these three films – Wes Anderson, Richard Linklater, and Kevin Smith, respectively – all went on to direct movies with bigger budgets, at least one of which for each filmmaker also appears on our list. The 1990s helped establish this now common trend in filmmaking of starting with small budget movies before getting to direct bigger budget movies, somewhat similar to minor league athletes being pulled up to the majors.

Source: Courtesy of Sony Pictures Releasing

75. Bottle Rocket (1996)
> Director: Wes Anderson
> Starring: Luke Wilson, Owen Wilson, Ned Dowd
> Domestic box office: $0.56 million

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Source: Courtesy of Miramax

74. The Mighty (1998)
> Director: Peter Chelsom
> Starring: Kieran Culkin, Elden Henson, Sharon Stone
> Domestic box office: $2.64 million

Source: Courtesy of October Films

73. Cookie’s Fortune (1999)
> Director: Robert Altman
> Starring: Glenn Close, Julianne Moore, Liv Tyler
> Domestic box office: $10.92 million

Source: Courtesy of Cinecom Pictures

72. Rosencrantz & Guildenstern Are Dead (1990)
> Director: Tom Stoppard
> Starring: Gary Oldman, Tim Roth, Richard Dreyfuss
> Domestic box office: $0.74 million

Source: Courtesy of TriStar Pictures

71. Jerry Maguire (1996)
> Director: Cameron Crowe
> Starring: Tom Cruise, Cuba Gooding Jr., Renée Zellweger
> Domestic box office: $153.95 million

Source: Courtesy of Fine Line Features

70. Twelfth Night or What You Will (1996)
> Director: Trevor Nunn
> Starring: Helena Bonham Carter, Richard E. Grant, Imogen Stubbs
> Domestic box office: $0.55 million

Source: Courtesy of Gramercy Pictures

69. Mystery Science Theater 3000: The Movie (1996)
> Director: Jim Mallon
> Starring: Trace Beaulieu, Michael J. Nelson, Jim Mallon
> Domestic box office: $1.01 million

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Source: Courtesy of Twentieth Century Fox

68. Ever After: A Cinderella Story (1998)
> Director: Andy Tennant
> Starring: Drew Barrymore, Anjelica Huston, Dougray Scott
> Domestic box office: $65.71 million

Source: Courtesy of Sony Pictures Classics

67. Sweet and Lowdown (1999)
> Director: Woody Allen
> Starring: Sean Penn, Samantha Morton, Woody Allen
> Domestic box office: $4.20 million

Source: Courtesy of Walt Disney Studios Motion Pictures

66. A Bug’s Life (1998)
> Director: John Lasseter, Andrew Stanton
> Starring: Kevin Spacey, Dave Foley, Julia Louis-Dreyfus
> Domestic box office: $162.80 million

Source: Courtesy of Fox Searchlight Pictures

65. Waking Ned Devine (1998)
> Director: Kirk Jones
> Starring: Ian Bannen, David Kelly, Fionnula Flanagan
> Domestic box office: $24.79 million

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Source: Courtesy of New Line Cinema

64. Pleasantville (1998)
> Director: Gary Ross
> Starring: Tobey Maguire, Jeff Daniels, Joan Allen
> Domestic box office: $40.57 million

Source: Courtesy of Miramax

63. Beautiful Girls (1996)
> Director: Ted Demme
> Starring: Matt Dillon, Timothy Hutton, Noah Emmerich
> Domestic box office: $10.60 million

Source: Courtesy of Miramax

62. Flirting with Disaster (1996)
> Director: David O. Russell
> Starring: Ben Stiller, Patricia Arquette, Téa Leoni
> Domestic box office: $14.89 million

Source: Courtesy of Fine Line Features

61. Trick (1999)
> Director: Jim Fall
> Starring: Christian Campbell, John Paul Pitoc, Tori Spelling
> Domestic box office: $2.05 million

Source: Courtesy of Metro-Goldwyn-Mayer

60. Get Shorty (1995)
> Director: Barry Sonnenfeld
> Starring: Gene Hackman, Rene Russo, Danny DeVito
> Domestic box office: $72.08 million

Source: Courtesy of Orion Classics

59. Trees Lounge (1996)
> Director: Steve Buscemi
> Starring: Steve Buscemi, Carol Kane, Mark Boone Junior
> Domestic box office: $0.70 million

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Source: Courtesy of Universal Pictures

58. Crooklyn (1994)
> Director: Spike Lee
> Starring: Alfre Woodard, Delroy Lindo, David Patrick Kelly
> Domestic box office: $13.64 million

Source: Courtesy of Columbia Pictures

57. Men in Black (1997)
> Director: Barry Sonnenfeld
> Starring: Tommy Lee Jones, Will Smith, Linda Fiorentino
> Domestic box office: $250.69 million

Source: Courtesy of New Line Cinema

56. Wag the Dog (1997)
> Director: Barry Levinson
> Starring: Dustin Hoffman, Robert De Niro, Anne Heche
> Domestic box office: $43.02 million

Source: Courtesy of Miramax

55. Chasing Amy (1997)
> Director: Kevin Smith
> Starring: Ben Affleck, Joey Lauren Adams, Ethan Suplee
> Domestic box office: $12.01 million

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Source: Courtesy of TriStar Pictures

54. As Good as It Gets (1997)
> Director: James L. Brooks
> Starring: Jack Nicholson, Helen Hunt, Greg Kinnear
> Domestic box office: $148.48 million

Source: Courtesy of Warner Bros.

53. Dogfight (1991)
> Director: Nancy Savoca
> Starring: River Phoenix, Lili Taylor, Richard Panebianco
> Domestic box office: $0.39 million

Source: Courtesy of Warner Bros.

52. Three Kings (1999)
> Director: David O. Russell
> Starring: George Clooney, Mark Wahlberg, Ice Cube
> Domestic box office: $60.65 million

Source: Courtesy of TriStar Pictures

51. Manhattan Murder Mystery (1993)
> Director: Woody Allen
> Starring: Woody Allen, Diane Keaton, Jerry Adler
> Domestic box office: $11.29 million

Source: Courtesy of TriStar Pictures

50. The Fisher King (1991)
> Director: Terry Gilliam
> Starring: Jeff Bridges, Robin Williams, Adam Bryant
> Domestic box office: $41.90 million

Source: Courtesy of The Samuel Goldwyn Company

49. Much Ado About Nothing (1993)
> Director: Kenneth Branagh
> Starring: Kenneth Branagh, Emma Thompson, Keanu Reeves
> Domestic box office: $22.55 million

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Source: Courtesy of Paramount Pictures

48. South Park: Bigger, Longer & Uncut (1999)
> Director: Trey Parker
> Starring: Trey Parker, Matt Stone, Mary Kay Bergman
> Domestic box office: $52.01 million

Source: Courtesy of Fine Line Features

47. Night on Earth (1991)
> Director: Jim Jarmusch
> Starring: Winona Ryder, Gena Rowlands, Lisanne Falk
> Domestic box office: $2.02 million

Source: Courtesy of Paramount Pictures

46. Bob Roberts (1992)
> Director: Tim Robbins
> Starring: Tim Robbins, Giancarlo Esposito, Alan Rickman
> Domestic box office: $4.48 million

Source: Courtesy of Columbia Pictures

45. Go (1999)
> Director: Doug Liman
> Starring: Sarah Polley, Jay Mohr, Scott Wolf
> Domestic box office: $16.84 million

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Source: Courtesy of USA Films

44. A Room for Romeo Brass (1999)
> Director: Shane Meadows
> Starring: Martin Arrowsmith, Dave Blant, Darren Campbell
> Domestic box office: $0.02 million

Source: Courtesy of Warner Bros.

43. Arizona Dream (1993)
> Director: Emir Kusturica
> Starring: Johnny Depp, Jerry Lewis, Faye Dunaway
> Domestic box office: $0.11 million

Source: Courtesy of Buena Vista Pictures Distribution

42. Grosse Pointe Blank (1997)
> Director: George Armitage
> Starring: John Cusack, Minnie Driver, Dan Aykroyd
> Domestic box office: $28.01 million

Source: Courtesy of Universal Pictures

41. Army of Darkness (1992)
> Director: Sam Raimi
> Starring: Bruce Campbell, Embeth Davidtz, Marcus Gilbert
> Domestic box office: $11.50 million

Source: Courtesy of Orion Classics

40. Slacker (1991)
> Director: Richard Linklater
> Starring: Richard Linklater, Rudy Basquez, Jean Caffeine
> Domestic box office: $1.23 million

Source: Courtesy of Fine Line Features

39. Deconstructing Harry (1997)
> Director: Woody Allen
> Starring: Woody Allen, Judy Davis, Julia Louis-Dreyfus
> Domestic box office: $10.57 million

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Source: Courtesy of Geffen Pictures

38. The Butcher Boy (1997)
> Director: Neil Jordan
> Starring: Stephen Rea, Fiona Shaw, Eamonn Owens
> Domestic box office: $1.82 million

Source: Courtesy of Paramount Pictures

37. Election (1999)
> Director: Alexander Payne
> Starring: Matthew Broderick, Reese Witherspoon, Chris Klein
> Domestic box office: $14.88 million

Source: Courtesy of Lions Gate Films

36. Buffalo ’66 (1998)
> Director: Vincent Gallo
> Starring: Vincent Gallo, Christina Ricci, Ben Gazzara
> Domestic box office: $2.38 million

Source: Courtesy of Twentieth Century Fox

35. Office Space (1999)
> Director: Mike Judge
> Starring: Ron Livingston, Jennifer Aniston, David Herman
> Domestic box office: $10.82 million

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Source: Courtesy of Miramax

34. Smoke Signals (1998)
> Director: Chris Eyre
> Starring: Adam Beach, Evan Adams, Irene Bedard
> Domestic box office: $6.72 million

Source: Courtesy of Sony Pictures Classics

33. Henry Fool (1997)
> Director: Hal Hartley
> Starring: Thomas Jay Ryan, James Urbaniak, Parker Posey
> Domestic box office: $1.34 million

Source: Courtesy of Twentieth Century Fox

32. The Commitments (1991)
> Director: Alan Parker
> Starring: Robert Arkins, Michael Aherne, Angeline Ball
> Domestic box office: $14.92 million

Source: Courtesy of Sony Pictures Classics

31. Living in Oblivion (1995)
> Director: Tom DiCillo
> Starring: Steve Buscemi, Catherine Keener, Dermot Mulroney
> Domestic box office: $1.15 million

Source: Courtesy of Warner Bros.

30. Defending Your Life (1991)
> Director: Albert Brooks
> Starring: Albert Brooks, Meryl Streep, Rip Torn
> Domestic box office: $16.37 million

Source: Courtesy of Miramax

29. Shakespeare in Love (1998)
> Director: John Madden
> Starring: Gwyneth Paltrow, Joseph Fiennes, Geoffrey Rush
> Domestic box office: $100.32 million

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Source: Courtesy of Miramax

28. Clerks (1994)
> Director: Kevin Smith
> Starring: Brian O’Halloran, Jeff Anderson, Marilyn Ghigliotti
> Domestic box office: $3.15 million

Source: Courtesy of Miramax

27. Swingers (1996)
> Director: Doug Liman
> Starring: Vince Vaughn, Heather Graham, Jon Favreau
> Domestic box office: $4.51 million

Source: Courtesy of Paramount Pictures

26. Nobody’s Fool (1994)
> Director: Robert Benton
> Starring: Paul Newman, Bruce Willis, Jessica Tandy
> Domestic box office: $39.49 million

Source: Courtesy of G2 Films

25. Topsy-Turvy (1999)
> Director: Mike Leigh
> Starring: Jim Broadbent, Allan Corduner, Dexter Fletcher
> Domestic box office: $6.20 million

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Source: Courtesy of Sony Pictures Classics

24. In the Company of Men (1997)
> Director: Neil LaBute
> Starring: Aaron Eckhart, Matt Malloy, Stacy Edwards
> Domestic box office: $2.86 million

Source: Courtesy of Fine Line Features

23. Trust (1990)
> Director: Hal Hartley
> Starring: Adrienne Shelly, Martin Donovan, Rebecca Nelson
> Domestic box office: $0.36 million

Source: Courtesy of Sony Pictures Classics

22. Welcome to the Dollhouse (1995)
> Director: Todd Solondz
> Starring: Heather Matarazzo, Christina Brucato, Victoria Davis
> Domestic box office: $4.77 million

Source: Courtesy of The Samuel Goldwyn Company

21. The Wedding Banquet (1993)
> Director: Ang Lee
> Starring: Winston Chao, May Chin, Ah-Lei Gua
> Domestic box office: $6.93 million

Source: Courtesy of Warner Bros.

20. The Iron Giant (1999)
> Director: Brad Bird
> Starring: Eli Marienthal, Harry Connick Jr., Jennifer Aniston
> Domestic box office: $23.16 million

Source: Courtesy of Gramercy Pictures

19. Dazed and Confused (1993)
> Director: Richard Linklater
> Starring: Jason London, Wiley Wiggins, Matthew McConaughey
> Domestic box office: $7.99 million

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Source: Courtesy of Columbia Pictures

18. Groundhog Day (1993)
> Director: Harold Ramis
> Starring: Bill Murray, Andie MacDowell, Chris Elliott
> Domestic box office: $70.91 million

Source: Courtesy of New Line Cinema

17. Metropolitan (1990)
> Director: Whit Stillman
> Starring: Carolyn Farina, Edward Clements, Chris Eigeman
> Domestic box office: $2.94 million

Source: Courtesy of Miramax

16. Bullets Over Broadway (1994)
> Director: Woody Allen
> Starring: John Cusack, Dianne Wiest, Jennifer Tilly
> Domestic box office: $13.38 million

Source: Courtesy of Miramax

15. Smoke (1995)
> Director: Wayne Wang, Paul Auster
> Starring: Harvey Keitel, William Hurt, Giancarlo Esposito
> Domestic box office: $8.35 million

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Source: Courtesy of Walt Disney Studios Motion Pictures

14. Aladdin (1992)
> Director: Ron Clements, John Musker
> Starring: Scott Weinger, Robin Williams, Linda Larkin
> Domestic box office: $217.35 million

Source: Courtesy of Twentieth Century Fox

13. Barton Fink (1991)
> Director: Joel Coen, Ethan Coen
> Starring: John Turturro, John Goodman, Judy Davis
> Domestic box office: $6.15 million

Source: Courtesy of Castle Rock Entertainment

12. Waiting for Guffman (1996)
> Director: Christopher Guest
> Starring: Christopher Guest, Fred Willard, Catherine O’Hara
> Domestic box office: $2.92 million

Source: Courtesy of USA Films

11. Being John Malkovich (1999)
> Director: Spike Jonze
> Starring: John Cusack, Cameron Diaz, Catherine Keener
> Domestic box office: $22.86 million

Source: Courtesy of Walt Disney Studios Motion Pictures

10. Toy Story 2 (1999)
> Director: John Lasseter, Ash Brannon, Lee Unkrich
> Starring: Tom Hanks, Tim Allen, Joan Cusack
> Domestic box office: $245.85 million

Source: Courtesy of Fine Line Features

9. Short Cuts (1993)
> Director: Robert Altman
> Starring: Andie MacDowell, Julianne Moore, Tim Robbins
> Domestic box office: $6.11 million

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Source: Courtesy of Gramercy Pictures

8. The Big Lebowski (1998)
> Director: Joel Coen, Ethan Coen
> Starring: Jeff Bridges, John Goodman, Julianne Moore
> Domestic box office: $17.50 million

Source: Courtesy of Walt Disney Studios Motion Pictures

7. Rushmore (1998)
> Director: Wes Anderson
> Starring: Jason Schwartzman, Bill Murray, Olivia Williams
> Domestic box office: $17.11 million

Source: Courtesy of Good Machine

6. Happiness (1998)
> Director: Todd Solondz
> Starring: Jane Adams, Jon Lovitz, Philip Seymour Hoffman
> Domestic box office: $2.81 million

Source: Courtesy of Walt Disney Studios Motion Pictures

5. Ed Wood (1994)
> Director: Tim Burton
> Starring: Johnny Depp, Martin Landau, Sarah Jessica Parker
> Domestic box office: $5.89 million

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Source: Courtesy of TriStar Pictures

4. Husbands and Wives (1992)
> Director: Woody Allen
> Starring: Woody Allen, Mia Farrow, Sydney Pollack
> Domestic box office: $10.56 million

Source: Courtesy of Paramount Pictures

3. The Truman Show (1998)
> Director: Peter Weir
> Starring: Jim Carrey, Ed Harris, Laura Linney
> Domestic box office: $125.62 million

Source: Courtesy of New Line Cinema

2. The Player (1992)
> Director: Robert Altman
> Starring: Tim Robbins, Greta Scacchi, Fred Ward
> Domestic box office: $21.71 million

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Source: Courtesy of Walt Disney Studios Motion Pictures

1. Toy Story (1995)
> Director: John Lasseter
> Starring: Tom Hanks, Tim Allen, Don Rickles
> Domestic box office: $191.80 million

Methodology:
To determine the best movies of the 1990s, 24/7 Wall St. created an index based on each film’s Rotten Tomatoes average critic rating, Rotten Tomatoes average audience rating, and Internet Movie Database average user rating. To be considered, each film had to have at least 10,000 total user ratings between IMDb and Rotten Tomatoes,10 approved Tomatometer critic reviews, and be labelled “comedy” by IMDb.

We averaged the user ratings from Rotten Tomatoes and IMDb and weighted by the number of votes for each. The combined user rating was then averaged with the Rotten Tomatoes critic rating. Box office data comes from IMDb and is not adjusted for inflation.