Devin Herenda 
19 Best ’90s Comedies
The ’90s were filled with a variety of hilarious flicks. But, TBH, with actors like Jim Carrey, Whoopi Goldberg, and Chris Farley leading popular comedies, you really couldn’t go wrong.
Touchstone Pictures / Via youtube.com youtube.comYears of release: 1991, 1995
Starring: Steve Martin, Martin Short, Diane Keaton, Kimberly Williams-Paisley
In this retelling of a ’50s comedy, Steve Martin played George Banks, a stressed out dad whose daughter, Annie (Kimberly Williams-Paisley), reveals she’s gotten engaged while traveling for her study abroad program. Annie gets married during Father of the Bride, while in the hilarious sequel, both she and her mom, Nina (Diane Keaton), become pregnant at the same time.
3. Happy Gilmore
Universal PicturesYear of release: 1996
Starring: Adam Sandler, Julie Bowen, Christopher McDonald, Frances Bay
When Happy Gilmore (Adam Sandler) learns his grandmother (Frances Bay) may soon lose her home, he decides to enter a golf tournament that can earn him enough money to save the day. In the process, he gains the attention of golf fans due to his tempestuous demeanor and one-of-a-kind swing.
4. Clueless
Paramount Pictures / Via youtube.comYear of release: 1995
Starring: Alicia Silverstone, Stacey Dash, Brittany Murphy, Paul Rudd
Did you think we’d forget this epic ’90s teen comedy? As if! Aside from serving many fun fashion looks, Clueless was filled with laugh-out-loud moments of wealthy Beverly Hills teens navigating their everyday high school experiences.
5. Rookie of the Year
Twentieth Century FoxYear of release: 1993
Starring: Thomas Ian Nicholas, Garey Busey, Amy Morton
After breaking his arm in an accident, pre-teen Henry Rowengartner (Thomas Ian Nicholas) is left with an amazing pitching arm that lands him a spot on the Chicago Cubs roster. This film was a sporty, family-friendly option that ’90s kids definitely had on their watchlist.
6. Sister Act and Sister Act 2: Back in the Habit
Touchstone PicturesYears of release: 1992, 1993
Starring: Whoopi Goldberg, Kathy Najimy, Maggie Smith
Whoopi led the films as Deloris Van Cartier, a Las Vegas singer who is placed in a convent after witnessing a murder orchestrated by her mobster boyfriend. In the sequel, Deloris returns to her role as a nun and passes along her music knowledge to a group of troubled students.
7. Mrs. Doubtfire
Twentieth Century Fox / Via youtube.comYear of release: 1993
Starring: Robin Williams, Sally Field, Pierce Brosnan
Robin Williams took on the role of Daniel Hillard, a man who poses as a female nanny following his porce in order to spend more time with his three children. Mrs. Doubtfire is one of the late comedy legend’s most unforgettable ’90s performances, and it had a great supporting cast, including Mara Wilson making her big-screen debut.
8. Heavyweights
Buena Vista Pictures / Courtesy Everett CollectionYear of release: 1995
Starring: Ben Stiller, Tom McGowan, Aaron Schwartz, Paul Feig
Before he portrayed White Goodman in Dodgeball, Ben Stiller played another extreme health guru, Tony Perkis, in Heavyweights. The character purchases a kids’ weight loss camp, but his out-of-control strictness soon becomes too much to take, which causes camp attendees to revolt. A young Kenan Thompson is included in the cast, and the film is also one of Judd Apatow’s earliest writing credits.
9. White Men Can’t Jump.
©20thCentFox / Courtesy Everett CollectionYear of release: 1992
Starring: Wesley Snipes, Woody Harrelson, Rosie Perez
After Sidney (Wesley Snipes) is hustled by Billy (Woody Harrelson), a white street basketball player, the two team up to con players throughout LA. Make sure to rewatch this classic before Jack Harlow makes his film debut in its upcoming remake.
10. 10 Things I Hate About You
Touchstone Pictures / Courtesy Everett CollectionYear of release: 1999
Starring: Julia Stiles, Larisa Oleynik, Heath Ledger, Joseph Gordon-Levitt
This 1999 movie adapted Shakespeare’s The Taming of the Shrew with a modern take on the story. Bianca Stratford (Larisa Oleynik) is told by her protective father (Larry Miller) she can only go out on dates when her sister, Kat (Julia Stiles), starts dating. To make this happen, Cameron (Joseph Gordon-Levitt), a classmate who is crushing on Bianca, schemes up a plan that will make Kat fall for bad boy Patrick Verona (Heath Ledger).
11. Tommy Boy
Broadway Pictures / Via youtube.comYear of release: 1995
Starring: Chris Farley, David Spade, Rob Lowe, Bo Derek
Tommy (Chris Farley) goes on an adventure to save his late father’s (Brian Dennehy) automobile parts business with Richard (David Spade), who works for the company. With Saturday Night Live alums and real-life friends — (the late) Chris Farley and David Spade — bringing the laughs in these lead parts, the movie proved their television chemistry was just as entertaining in cinema.
12. The Big Lebowski
Polygram Filmed Entertainment / Via youtube.comYear of release: 1998
Starring: Jeff Bridges, Julianne Moore, John Goodman, Steve Buscemi
Jeff “The Dude” Lebowski (Jeff Bridges) is confused with another Jeff Lebowski (David Huddleston), a millionaire whose kidnapped wife (Tara Reid) owes big money to shady characters. When he seeks out the other Lebowski, The Dude gets mixed up in this tricky situation and calls on his bowling friends (John Goodman, Steve Buscemi) to help him navigate his unexpected circumstances.
13. Wayne’s World
Paramount Pictures / Via youtube.comYear of release: 1992
Starring: Mike Myers, Dana Carvey, Rob Lowe, Tia Carrere
This comedy saw a successful recurring Saturday Night Live skit move to the big screen. Wayne (Mike Myers) and Garth (Dana Carvey) are offered to air their Wayne’s World show on a local TV station by a seedy producer (Rob Lowe) in the film, which later had an entertaining sequel.
14. Dumb and Dumber
New Line CinemaYear of release: 1994
Starring: Jim Carrey, Jeff Daniels, Lauren Holly
Harry (Jeff Daniels) and Lloyd (Jim Carrey) cracked up viewers as they set out to return a cash-filled briefcase to its owner, a woman named Mary (Lauren Holly). Moviegoers petitioned for a Dumb and Dumber part two for years until a sequel was released in 2014.
15. The Wedding Singer
Juno PixYear of release: 1998
Starring: Adam Sandler, Drew Barrymore, Christine Taylor
The first film collaboration between Adam Sandler and Drew Barrymore was both romantic and hilarious. In a mid-’80s setting, Robbie (Adam), a wedding singer, falls for Julia (Drew) as he’s planning her impending nuptials.
16. My Cousin Vinny
20thcentfox / ©20thCentFox/Courtesy Everett CollectionYear of release: 1992
Starring: Joe Pesci, Marisa Tomei, Ralph Macchio
It’s been 30 years since My Cousin Vinny, which scored an Oscar for Marisa Tomei, was released and it still holds up. With his fiancée, Mona Lisa Vito (Marisa) by his side, New Yorker Vinny Gambini (Joe Pesci) serves as an attorney for his cousin Bill (Ralph Macchio), who’s wrongfully been accused of murder.
17. What About Bob?
Touchstone Pictures / Via youtube.comYear of release: 1991
Starring: Bill Murray, Richard Dreyfuss, Julie Hagerty
Bob Wiley (Bill Murray) is a patient of Dr. Leo Marvin (Richard Dreyfuss), a psychotherapist and author who is at the top of his professional game. Leo travels with his family to Lake Winnipesaukee for a trip, and Bob decides to follow. During this vacation, Bob begins to benefit from Leo’s teachings, while Leo is quickly driven crazy by his patient’s presence.
18. Home Alone
Twentieth Century Fox / Via youtube.comYear of release: 1990
Starring: Macaulay Culkin, Joe Pesci, Daniel Stern, Catherine O’Hara
The first Home Alone franchise film introduced Macaulay Culkin as Kevin McCallister, a kid who fights off intruders Harry (Joe Pesci) and Marv (Daniel Stern) when his family accidentally leaves him at home during their Christmas vacation. Macaulay, Joe, Daniel, and more lead actors returned to their roles for Home Alone 2: Lost in New York.
19. House Party
New Line Cinema/Courtesy Everett CollectionYear of release: 1990
Starring: Christopher Reid, Christopher Martin, Robin Harris
Christopher Reid and Christopher Martin of Kid ‘n Play starred in this musical comedy about a wild night of party escapades. The hip-hop duo went on to act in four more films together after this one, and there is now a House Party reboot on the way.
What other ’90s movies would you add to this list?
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