The 12 Most Hilarious Comedy Films of the '90s

      Here are the 12 funniest comedy films from the '90s—a list that highlights how this decade might have been the ultimate era for comedies.

      While numerous excellent '90s films technically belong to the comedy genre, many don't consistently generate laughter. Those films are not included here. This list features the most hilarious comedies from the '90s, the kind that will leave you chuckling even if you feel a bit guilty for doing so. Aren't those the best?

      Do you disagree? Think we overlooked a hilariously funny '90s comedy? Share your thoughts in the comments. Now, here's our list.

      **Groundhog Day (1993)**

      Columbia Pictures – Credit: C/O

      Harold Ramis’ *Groundhog Day* is not just one of the best comedy films ever but also ranks among the best films across all genres. Its depth almost led us to exclude it, as it seems more a profound reflection on life than a straightforward comedy.

      However, upon rewatching memorable moments, it's clear that the film is genuinely funny. Highlights include Ned Ryerson, the snowball fight, and the transformation of “I Got You Babe” into a symbol of despair.

      It's undoubtedly one of the funniest comedies of the '90s, even beyond its meaningful themes about love, self-betterment, and community.

      **Dumb and Dumber (1994)**

      New Line Cinema – Credit: Jim Carrey and Jeff Daniels in *Dumb and Dumber*, New Line Cinema

      You must embrace the silliness of *Dumb and Dumber*, which served the '90s similarly to how Airplane! creators Zucker-Abrahams-Zucker did for the '80s. The film features Jim Carrey and Jeff Daniels as two lovable idiots on a journey from Providence, Rhode Island, to Aspen, Colorado, to return a briefcase stuffed with cash.

      These clueless characters are drawn into a web of adult deception but maintain their inherent sweetness. Our favorite moment is the mix-up between Austria and Australia— a mistake we made in our youth — and the hilarious van-for-scooter trade: “I can get 70 miles to the gallon for this hog.”

      Carrey was an immense comedy star at the time of the film's release, but Daniels grounded the film with his sincere performance.

      **Fear of a Black Hat (1994)**

      The Samuel Goldwyn Company – Credit: C/O

      Featuring Rusty Cundieff, who both wrote and directed, *Fear of a Black Hat* offers a sharp satire on the ever-evolving trends in hip-hop, capturing them as quickly as they emerged. While it may not be as widely known as others on this list, it's packed with clever observations that resonate.

      The film, which debuted at Sundance, follows a political gangsta rap group called NWH (the "H" stands for hats) as they splinter into various genres, including aggressive diss tracks and dance music reminiscent of C&C Music Factory.

      It's an excellent time capsule of hip-hop’s rise, and its humor remains intact regardless of whether you catch all the specific cultural references.

      **Billy Madison (1995)**

      Universal Pictures – Credit: C/O

      Adam Sandler delivers plenty of laughs throughout *Billy Madison*, the tale of a man returning to school—starting from the ground up. One of the best aspects of Sandler's comedies is how he showcases his friends' talents.

      Two memorable scenes stick out. In one, Steve Buscemi receives an apology from Billy for bullying him in high school and crosses Billy off his 'People to Kill’ list.

      In the other, understated SNL icon James Downey delivers a highly quotable insult regarding Billy’s disastrous Academic Decathlon answer, concluding, “I award you no points, and may God have mercy on your soul.”

      **Clueless (1995)**

      Paramount Pictures – Credit: C/O

      Beyond being a quintessential representation of '90s culture— with its iconic mall scenes—*Clueless* is filled with witty dialogue, as a good Jane Austen adaptation should be.

      The film thrives on Alicia Silverstone's charm and introduces us to the endearing Paul Rudd, who would go on to enjoy immense popularity.

      One memorable line, perhaps no longer deemed appropriate to laugh at, comes from Donald Faison: “Are you b— blind or something? Your man Christian is a cakeboy. He’s a disco-dancin’, Oscar Wilde-readin’, Streisand ticket-holdin’ friend of Dorothy.”

      As one popular YouTube comment noted: “It’s adorable how he can list all these identifiers without actually being INSULTING or homophobic!”

      It's one of the '90s comedies that still feels incredibly relevant.

      **Tommy Boy (1995)**

      Paramount – Credit: Paramount Pictures

      The 30th anniversary of *Tommy Boy* has sparked renewed attention for this classic starring David