10 best comedies of the 1990s, ranked

The 1990s was one of the biggest decades for comedy films. Filmmakers pushed cultural boundaries, experimented with new ideas, and blended genres to create unique and gut-busting viewing experiences.

Contents

• 10. Waiting For Guffman (1996)
• 9. Office Space (1999)
• 8. Austin Powers: International Man of Mystery (1997)
• 7. My Cousin Vinny (1992)
• 6. The Birdcage (1996)
• 5. There’s Something About Mary (1998)
• 4. The Big Lebowski (1998)
• 3. Home Alone (1990)
• 2. The Truman Show (1998)
• 1. Groundhog Day (1993)
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Comedy has evolved and progressed since the turn of the century, but nostalgia aside, the films of this bygone era retain a charm that makes audiences return to them all these years later. With that in mind, it’s time to look at the best comedy films from the ’90s.

10. Waiting For Guffman (1996)

“Everybody dance!” In this mockumentary film, a group of oddball performers put together a theater production about the wild history of their town, hoping to impress the Broadway producer they’ve invited to the play.

With a spectacular ensemble cast featuring Christopher Guest, Eugene Levy, Catherine O’Hara, Parker Posey, and Fred Willard, Schitt’s Creek fans will enjoy this quirky small-town film and its comedic and tragic tale of a (sort-of) regular group of people reaching for the stars.

9. Office Space (1999)

Sick of their soul-sucking cubicle jobs, three white-collar workers (Loudermilk‘s Ron Livingston, David Herman, and Ajay Naidu) hatch a scheme to steal money from their company and get back at their corporate oppressors.

Much like The Office, this cult classic pokes fun at the annoying workplace absurdities many real people have experienced, making for a relatable and side-splitting tale of the little guys sticking it to their bosses.

8. Austin Powers: International Man of Mystery (1997)

They don’t do parody movies like these used to. In a ridiculous spoof of the James Bond movies, ’60s secret agent Austin Powers freezes himself to stop his nemesis Dr. Evil from destroying the world in the ’90s.

Poking fun at the many tired tropes found in the 007 franchise, International Man of Mystery features scene after scene of laugh-out-loud bits and characters, with Mike Myers stealing the show in a smashing and legendary dual performance.

7. My Cousin Vinny (1992)

When two New Yorkers (Ralph Macchio and Mitchell Whitfield) are arrested in Alabama, one calls his cousin Vinny (Joe Pesci), a novice lawyer, to drive down to defend them both in court, making for a hilarious fish-out-of-water story.

Pesci and his co-star Marisa Tomei deliver electrifying performances in this film, and its surprisingly realistic depiction of the criminal justice system has held it up in the decades since its release.

6. The Birdcage (1996)

When his son (Dan Futterman) gets engaged, a drag club owner (Robin Williams) and his partner (Nathan Lane) try to hide their homosexuality in front of his fiancée’s conservative parents (Gene Hackman and Dianne Wiest).

Revolutionary for its positive LGBTQ+ representation with its main characters, this hysterical and profound comedy opened the door for other major Hollywood films to depict similar stories on the big screen.

5. There’s Something About Mary (1998)

After an obsessed man (Ben Stiller) tracks down his high school crush (Cameron Diaz), he competes with several other suitors for her heart. Starting with the infamous “frank and beans” fiasco, this film delivers so many wacky and shocking moments that audiences can’t help but laugh at.

There’s Something About Mary certainly couldn’t be made today, but 25 years later, it remains one of the most outrageous rom-coms ever made.

4. The Big Lebowski (1998)

When The Dude (Jeff Bridges) is mistaken for an indebted millionaire (David Huddleston) with his exact name, he and his bowling pals (John Goodman and Steve Buscemi) get swept up in a wild adventure through the weird world of Los Angeles.

This film is filled with a variety of quirky characters, from the nihilistic, Johnson-snatching Germans to the perverted bowler Jesus (John Turturro) to the Dude’s scene-stealing friend, Walter. But it’s Jeff Bridges’ iconic character that elevates this absurdist odyssey to the cult classic it is today.

3. Home Alone (1990)

When eight-year-old Kevin (Macaulay Culkin) gets left behind by his family during Christmas vacation, he must defend their house from being robbed by two bumbling bandits (Joe Pesci and Daniel Stern).

Many audiences have fond holiday memories of watching Kevin torture Harry and Marv on Christmas Eve. But this movie is more than a night of Tom & Jerry-style mayhem. There’s plenty of heart to be found as Kevin learns to take care of himself and sees the world past the veneer of childhood.

2. The Truman Show (1998)

As an ordinary man (Jim Carrey) discovers his life and everyone in it is part of a reality TV show centered around him, he must overcome his fears and decide whether or not he wants to see the real world waiting behind the scenes.

It’s a clever satire poking fun at people’s obsession with celebrities and their private lives while also exploring how easily people can accept the world that’s presented to them. The Truman Show effectively blends witty comedy and heartfelt drama to present one of the most unconventional and moving blockbusters ever.

1. Groundhog Day (1993)

This groundbreaking comedy follows a loathsome weatherman (Bill Murray) who bas to relive the same day over and over again. In one of the most well-known cases of an existential crisis, protagonist Phil struggles to escape this loop and fails to enjoy his eternal life without consequence, only to finally find joy and meaning by supporting and connecting with others in the town he once hated.

Hilarious, heartfelt, and thought-provoking, Groundhog Day continues to be an inspiring classic that has even become a subgenre in itself.