The 12 Most Hilarious Comedy Films from the '90s

      Here are the 12 funniest comedy films from the '90s—a compilation that highlights how the '90s might just be the ultimate decade for comedies.

      There are numerous excellent '90s films that technically fit into the comedy genre, but they don't always evoke laughter. Those aren't included here. Instead, this list features the most hilarious '90s comedies—those guaranteed to make you chuckle, even if it causes you to question your own morality for enjoying them. Aren’t those the best kind?

      Have a differing opinion? Think we overlooked a particularly funny '90s comedy? Feel free to share your thoughts in the comments. Now, here’s our list.

      **Groundhog Day (1993)**

      Columbia Pictures – Credit: C/O

      Harold Ramis's Groundhog Day stands out as one of the greatest comedy films ever created, and also ranks among the best films of any genre. Its depth almost led us to omit it from this list, as it often feels more like a profound reflection on life disguised as a straightforward comedy.

      However, after revisiting some memorable scenes, we realized just how funny it really is. Ned Ryerson, the snowball fight, "He might be OK," and turning "I Got You Babe" into a tune of despair... there's so much more.

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

      **Dumb and Dumber (1994)**

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

      You must fully embrace the silliness of Dumb and Dumber, which was to the '90s what the creators of Airplane! were to the '80s. It all began with Dumb and Dumber, featuring Jim Carrey and Jeff Daniels as two endearing simpletons who journey from Providence, Rhode Island, to Aspen, Colorado, to return a briefcase filled with cash.

      The clueless duo gets drawn into a realm of adult deception, yet they maintain their inherent kindness. Our favorite moment is the mix-up between Austria and Australia—we made that same mistake as kids—and the trade of a van for a scooter: "I can get 70 miles per gallon for this hog."

      At the time of Dumb and Dumber’s release, Carrey was a major comedy sensation, while Daniels held his own by playing his role with authenticity. His performance anchors the entire film.

      **Fear of a Black Hat (1994)**

      The Samuel Goldwyn Company – Credit: C/O

      Featuring Rusty Cundieff, who also wrote and directed, Fear of a Black Hat is a clever satire of ever-changing hip-hop trends that respond to them almost in real-time. It might be the least recognized movie on this list, but it's packed with witty moments that linger in our minds.

      The film, which debuted at Sundance, follows a political/gangster rap group named NWH (the H stands for hats) that fractures into various sub-genres, including desperate diss tracks, P.M. Dawn-esque philosophizing, and dance music reminiscent of C&C Music Factory.

      It serves as a remarkable time capsule of the hip-hop explosion, with humor that remains relevant even if you don’t catch all the timely references.

      **Billy Madison (1995)**

      Universal Pictures – Credit: C/O

      Adam Sandler shines in Billy Madison, the tale of a man who must retake his education—from kindergarten onward. One of the best aspects of Sandler’s comedies is how he allows his friends to shine alongside him.

      Two scenes stand out in our memory. 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 another, understated SNL legend James Downey delivers a widely quoted critique of Billy’s abysmal Academic Decathlon response, concluding with, “I award you no points, and may God have mercy on your soul.”

      **Clueless (1995)**

      Paramount Pictures – Credit: C/O

      Beyond being a visual emblem of the '90s—the mall scenes are truly iconic—Clueless is brimming with sharp dialogue, as any worthwhile Jane Austen adaptation should be.

      Centered around Alicia Silverstone’s immense charm, it also showcased the understated appeal of Paul Rudd, who later became a significant star.

      Our favorite quote—perhaps one we shouldn’t find funny anymore—comes from future Scrubs star Donald Faison: “Are you b—— blind or something? Your man Christian is a cakeboy. He's a disco-dancing, Oscar Wilde-reading, Streisand ticket-holding friend of Dorothy.”

      As noted by a highly-upvoted YouTube commenter, “It’s adorkable how he can come up with so many identifiers without actually being INSULTING or homophobic!”

      It’s one of the