The Best Comedy Movies From The 90s

The Best Comedy Movies From The 90s
Best Comedies from the 90s

The 1990s produced some of the most hilarious and iconic comedy films that still have audiences roaring with laughter today. From clever satires and screwball comedies to outrageously silly slapstick, the 1990s was a golden decade for funny movies.

Let's take a nostalgic trip back and count down our pick of the 20 best comedy movies from the 1990s.

20. A Night At The Roxbury

Director: John Fortenberry

Cast: Will Ferrell, Chris Kattan

The brainless but lovable Butabi brothers Doug and Steve just want to party at the hippest club in town, but can they make it past the velvet rope? A Night at the Roxbury is absurd fun, with Will Ferrell and Chris Kattan bringing their popular SNL characters to the big screen.

  • Memorable head-bobbing dance scenes
  • Features early Will Ferrell comedy
  • Also stars Dan Hedaya and Molly Shannon

19. Clerks

Director: Kevin Smith

Cast: Brian O'Halloran, Jeff Anderson, and Marilyn Ghigliotti

Jay and Silent Bob

Made on a shoestring budget, Kevin Smith's directorial debut follows a day in the lives of convenience store clerks Dante and Randal. Clerks captures aimless twenty-something life with raw humour about minimum-wage jobs, hockey, relationships, and an escaped cheetah.

  • Launched Kevin Smith's career
  • Known for witty, irreverent dialogue
  • Shot in black and white
  • Introduced audiences to Jay and Silent Bob
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18. Dumb and Dumber

Director: The Farrelly Brothers

Cast: Jim Carrey, Jeff Daniels, Lauren Holly

In possibly his most unhinged comedic performance, Jim Carrey plays sweet yet dim-witted Lloyd, who hits the road to Aspen with his equally moronic best friend Harry (Jeff Daniels) in Dumb and Dumber. The classic comedy road trip has everything from VW Beetle hijinks to some nasty cases of diarrhoea.

  • Established the gross-out comedy style the Farrelly Brothers became known for
  • Featured Carrey at the height of his 90s comedic fame after Ace Ventura and The Mask
  • "No Way...We landed on the moon!"

17. The Cable Guy

Director: Ben Stiller

Cast: Jim Carrey, Matthew Broderick, and Leslie Mann

This dark comedy, starring Jim Carrey, took his manic comedic persona into deliciously creepy territory. Carrey plays the overly-friendly cable TV installer who infiltrates the life of Matthew Broderick’s character. Directed by Ben Stiller, the clever satire racks up big laughs while offering social commentary on technology, media, and the legal system.

  • One of Jim Carrey's most memorable performances
  • Features Ben Stiller in an early directing role
  • Includes a scene filmed at Mediaeval Times
  • Early role for Jack Black

16. Austin Powers: International Man of Mystery

Director: Jay Roach

Cast: Mike Myers, Elizabeth Hurley, and Michael York

Groovy, baby! Mike Myers brought his SNL character Austin Powers to the big screen in this colorful spoof on 60s culture and spy films. Myers plays both Powers, an out-of-touch British super spy cryogenically frozen since the 60s, and his nemesis Dr. Evil hellbent on world domination.

  • Made Mike Myers a bankable comedy movie star
  • Created instantly recognizable catchphrases like “Yeah, baby!”
  • Spawned a popular trilogy with The Spy Who Shagged Me (1999) and Goldmember (2002)
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15. My Cousin Vinny (1992)

Director: Jonathan Lynn

Cast: Joe Pesci, Marisa Tomei, Ralph Macchio, Mitchell Whitfield

My Cousin Vinny (1992)

Brooklyn lawyer Vinny gets in over his head when travels down South to defend his wrongly accused cousin and friend in this hilarious fish-out-of-water courtroom comedy. Joe Pesci shines with his electric, hot-headed energy against type as an inexperienced lawyer. Marisa Tomei also won an Oscar for her bubbly performance as Vinny's girlfriend.

  • Won Academy Award for Best Supporting Actress (Marisa Tomei)
  • Often considered one of Pesci's best comedic roles

14. Wayne's World

Director: Penelope Spheeris

Cast: Mike Myers, Dana Carvey, Tia Carrere

Party on! Wayne's World brings the beloved SNL sketch to the big screen in all its slacker glory. Mike Myers and Dana Carvey are iconic as rock n' roll cable access hosts Wayne and Garth who are trying to save their show from getting bought out by the slimy producer Benjamin (Rob Lowe).

  • Catchphrase “We're not worthy!”
  • Featured the now famous “Bohemian Rhapsody” lip syncing scene
  • Has a sequel Wayne's World 2 also released in 1993

13. The Mask

Director: Chuck Russell

Cast: Jim Carrey, Cameron Diaz, Peter Riegert

Jim Carrey's incredible elastic facial expressions and body were made for his role as timid bank clerk Stanley Ipkiss who finds a magical green mask granting him supernatural powers. With outlandish visual effects and cartoon logic, The Mask showcases Carrey at his most playful and unhinged. The film also features Cameron Diaz in her exciting film debut playing lounge singer Tina Carlyle.

  • Vibrant, over-the-top visual effects
  • Features early starring role for Cameron Diaz
  • Inspired an animated TV series spin-off
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12. Happy Gilmore

Director: Dennis Dugan

Cast: Adam Sandler, Christopher McDonald, Julie Bowen

Adam Sandler stars as a hot-tempered hockey player who discovers a hidden talent for golf with hysterical results. When Happy discovers his grandmother is about to lose her home, he sets out to win a golf tournament prize with his slap shot skills and aggressive antics to the horror of the golf pros.

  • Features Bobby Bowden, Bob Barker cameos
  • Established Adam Sandler's comedic film persona
  • Shows off his talent for blending crass humor with surprising warmth

11. Mrs. Doubtfire

Director: Chris Columbus

Cast: Robin Williams, Sally Field, Pierce Brosnan

After a messy divorce, desperate dad Daniel Hillard (Robin Williams) disguises himself as a kindly British housekeeper named Mrs. Doubtfire to secretly spend time with his kids. While hijinks ensue trying to maintain his double life, the Williams delivers a surprisingly poignant performance that balances slapstick comedy with family drama.

  • Won Academy Award for Best Makeup
  • Features Robin Williams at his comedic best
  • "Helloooooooo!"

10. Men in Black

Director: Barry Sonnenfeld

Cast: Will Smith, Tommy Lee Jones, Linda Fiorentino

Will Smith and Tommy Lee Jones have hilarious chemistry as secret agents policing extraterrestrial life hidden on Earth. The ultra hip Men in Black mixes quirky aliens, slick action sequences, and plenty of laughs. With its retro futurism aesthetic, the original blockbuster spawned two sequels and stands as one of the most enjoyable sci-fi comedies.

  • Earned 3 Academy Award nominations including Best Original Score
  • Catapulted Will Smith into box office superstardom
  • Features makeup and creature effects by legendary Rick Baker

9. Liar Liar

Director: Tom Shadyac

Cast: Jim Carrey, Maura Tierney, Justin Cooper, Cary Elwes

Jim Carrey is in top manic form playing sleazy lawyer and compulsive liar Fletcher Reede who suddenly finds himself unable to tell a lie. This uproarious comedy builds laughs upon laughs as Fletcher fumbles through a day in court and important meetings while bluntly spewing uncomfortable truths.

  • Features Jim Carrey's frantic physical comedy
  • Written by Paul Guay and Stephen Mazur
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8. Rush Hour

Director: Brett Ratner

Cast: Jackie Chan, Chris Tucker, Tom Wilkinson

Rush Hour

What happens when a straight-laced Hong Kong police inspector pairs up with a wisecracking LAPD detective? Rush Hour mixes Jackie Chan's jaw-dropping stunt work with Chris Tucker's motormouth comedy for a winning action-comedy combo. As the mismatched cops race to rescue a diplomat's kidnapped daughter, the laughs and butt-kicking never let up.

  • Buddy cop comedy lead to two sequels
  • Breakout Hollywood hit for Jackie Chan
  • Features Chris Tucker's fast-talking stand-up style

7. There's Something About Mary

Director: Bobby and Peter Farrelly

Cast: Cameron Diaz, Ben Stiller, Matt Dillon

The Farrelly Brothers pushed gross-out comedy to new extremes in this outrageous romantic comedy about a ragtag group of suitors fighting over the affections of dazzling optimist Mary (Cameron Diaz). Equal parts raunchy and sweet, There's Something About Mary set the template for R-rated laugh fests in the 2000s with its anything-goes hijinks and huge box office success.

  • Established the popular gross-out comedy style the Farrelly Brothers became known for
  • Features Cameron Diaz in her breakout starring role
  • Includes unforgettable hair gel scene

6. Kingpin

Director: Bobby & Peter Farrelly

Cast: Woody Harrelson, Randy Quaid, Vanessa Angel

Down-on-his luck former bowling champion Roy Munson (Woody Harrelson) sees his chance for million-dollar comeback if he can transform naive Amish talent Ishmael (Randy Quaid) into the next bowling superstar. Kingpin serves up plenty of ridiculous debauchery and hilarious sports comedy without any gutter balls.

  • Features early starring roles for Woody Harrelson and Randy Quaid
  • Known for Bill Murray's memorable supporting role and cameo
  • Often considered one of the Farrelly Brothers most underrated comedies

5. Office Space

Director: Mike Judge

Cast: Ron Livingston, Jennifer Aniston, David Herman

Office Space

Cult comedy classic Office Space ruthlessly mocks dead end corporate employment through the plight of bored IT workers Peter Gibbons (Ron Livingston) and Michael Bolton (David Herman) who hatch a plan to steal money from the soulless Initech company. Writer and director Mike Judge perfectly skewers office life in late 90s America from pointless meetings to malfunctioning printers.

  • Considered one of the most beloved workplace comedies
  • Features Jennifer Aniston in a supporting role
  • Inspired many cubicle drones to question their career choices

4. Grumpy Old Men

Director: Donald Petrie

Cast: Jack Lemmon, Walter Matthau, Ann-Margret

Grumpy Old Men

Lifelong neighborhood rivals Max (Walter Matthau ) and John (Jack Lemmon) find themselves still battling over the newest lovely resident on the block Ariel (Ann-Margret). Both comedy veterans are at their kvetching finest trading insults like a real life Felix and Oscar odd couple. Grumpy Old Men became an unlikely holiday classic comedy.

  • Pairing of classic Hollywood stars Walter Matthau and Jack Lemmon
  • Features Ann-Margret as charming love interest
  • Followed by a sequel Grumpier Old Men (1995) reuniting original cast

3. Groundhog Day

Director: Harold Ramis

Cast: Bill Murray, Andie MacDowell, Chris Elliott

Arrogant weather reporter Phil Connors finds himself stuck repeating February 2nd over and over again. As cynicism slowly transforms into optimism, Bill Murray delivers a tour de force comedic performance finding laughs and surprisingly thoughtful insights on self-improvement and the meaning of life. Groundhog Day proves prolifically funny, perfectly sweet and timelessly profound.

  • Regarded as one of Bill Murray's greatest comedic performances
  • Expert blend of clever comedy and philosophical depth
  • Inspired the phrase “Groundhog Day” meaning a repetitive, unpleasant situation

2. The Birdcage

Director: Mike Nichols

Cast: Robin Williams, Nathan Lane, Gene Hackman

Longtime lovers Armand and Albert own a drag club together in South Beach Miami. When Armand's son announces his engagement to the daughter of super conservative Senator Keeley (Gene Hackman), mayhem ensues trying to pass off flamboyant Albert as an uptight traditional housewife to appeal to the straight-laced future in-laws. Nathan Lane and Robin Williams make an uproarious comedic duo in this American adaptation of the classic French farce La Cage aux Folles.

  • First team-up between legendary comedians Robin Williams and Nathan Lane
  • Directed by Mike Nichols
  • Respectful portrayal of gay couple became cultural milestone

1. The Big Lebowski

Director: Joel Coen/ Ethan Coen

Cast: Jeff Bridges, John Goodman, Julianne Moore, Steve Buscemi

A stoner neo-noir crime comedy sounds impossible on paper but the Coen Brothers brilliantly pulled it off with The Big Lebowski. Jeff “Dude” Lebowski (Jeff Bridges) just wants compensation for his ruined rug after being assaulted when loan sharks mistake him for a different Lebowski. As circumstances spiral out of control, the Dude gets in over his head alongside his volatile best friend Walter Sobchak (John Goodman) and the colorful supporting characters. Behind the laughs, The Big Lebowski offers an unforgettable tribute to taking it easy as cosmic tumbleweed blowing through life’s absurdities.

  • Regarded as one of the greatest cult classic comedies
  • Features Jeff Bridges iconic performance as “the Dude”
  • Known for unique hybrid of stoner comedy and crime noir homage

And scene! While the 90s feels like a long time ago now, these fantastic comedy films have stood the test of time thanks to endless reruns and devoted fans passing them down to new generations. Though tastes and social standards evolve, human nature has stayed much the same, and these films expertly mine comedy that cuts straight to the core of the human experience. Great comedy connects us through shared laughter and continues offering escapes from life's hassles.