The 10 Funniest Movies of the 1990s

1. "Fargo " (1996)

"Fargo" isn't your typical comedy, but it certainly has elements that make you laugh at the sheer absurdity of it all. Jerry Lundegaard, a desperate car salesman, hatches a plan to have his wife kidnapped so he can collect the ransom from his wealthy father-in-law.

However, things don't go according to plan (as expected) when the kidnappers, Carl and Gaear, leave a trail of violence and blood. In the quiet, snow-filled landscapes of Minnesota, pregnant police chief Marge Gunderson starts connecting the dots, leading to a series of events that combine the sinister with the hilarious.

2. "Office Space" (1999)

"Office Space" takes us into the soul-sucking world of corporate monotony.

Peter Gibbons, stuck in a job he hates, undergoes hypnotherapy to care less about work but then his therapist just goes and dies mid-session, leaving Peter in a state of permanent apathy. He starts slacking off, destroying company property and even embezzles money, using a computer virus for help with that.

His newfound devil-may-care attitude towards his tedious job and the consequences it brings are relatable (even in 2023!) and hilariously entertaining.

3. "The Big Lebowski" (1998)

"The Big Lebowski" follows Jeff Lebowski, affectionately known as "The Dude." When two thugs mistake him for a millionaire with the same name, his rug gets ruined in the process. Seeking compensation for his rug, "The Dude" gets tangled in a convoluted plot involving the millionaire's debt, a kidnapping, nihilists, and a missing ransom.

Watching "The Dude's" laid-back attitude clashing with the increasing complexity of the situation around him is still entertaining, even all these years later.

4. "Clueless" (1995)

"Clueless" is a charming tale set in Beverly Hills, focusing on Cher Horowitz, a wealthy and popular high school student. Cher's life revolves around fashion, social status, and matchmaking, but when she tries to play cupid for two of her teachers and her seemingly unsophisticated friend Tai, things don't go as planned.

The mishaps and misunderstandings occur as Cher navigates her way through high school society, friendships, and unexpected feelings of love, and you just can't help but fall in love with her a bit more.

5. "Austin Powers: International Man of Mystery" (1997)

"Austin Powers: International Man of Mystery" is a spy parody that introduces us to Austin Powers, a 1960s secret agent cryogenically frozen and reanimated in the 1990s to combat his arch-nemesis, Dr. Evil. However, Austin finds that his 60s-era style and approach to espionage are out of place in the new world, leading to a series of comedic situations.

The absurdity of the spy plot, the time-travel, and Austin's flamboyant character are all quintessentially '90s, making this one a hilarious, if slightly outdated, watch.

6. "Groundhog Day" (1993)

"Groundhog Day" ensnares us in a temporal loop alongside its protagonist, Phil Connors. Phil, a weatherman, wakes each morning to find that it's Groundhog Day. Again. And again.

While initially bewildered, he eventually exploits the situation to his advantage. He learns the piano, becomes fluent in French, and even saves a life or two. However, the droll repetitiveness of his life gradually loses its charm. Phil ultimately learns that the way to break the cycle is through acts of kindness (not being a huge d*ck, basically) and genuine love for Rita, his producer.

7. "Home Alone " (1990)

Forgotten by his family during their Christmas vacation, Kevin McCallister finds himself in an adult-free paradise. However, his holiday takes a turn when he encounters the Wet Bandits, Harry and Marv, who plan to rob his house.

With a combination of quick-thinking and crafty traps, Kevin defends his home. His ingenious antics and the bandits' increasingly frustrated attempts at burglary is something that will never get old.

8. "Mrs. Doubtfire" (1993)

In "Mrs. Doubtfire," we follow Daniel Hillard, a man who goes to unimaginable lengths to be with his children after a painful divorce. Armed with his talent for voice acting and a convincing disguise as a British nanny, he fools his ex-wife into hiring him as a caretaker for their kids.

The absurdity of his double life, juxtaposed with the heartwarming bond he forms with his children, creates a delightful blend of humor and sentimentality. Feels just a tiny bit dated now in 2023, but then again, the theme of a parent going to great length to be with their kid? Timeless.

9. "Dumb and Dumber" (1994)

"Dumb and Dumber" takes us on a cross-country adventure with Harry and Lloyd, two friends whose combined intelligence leaves much to be desired.

When Lloyd becomes infatuated with a woman he drives to the airport, they set off to Aspen to return a briefcase she "forgot." Unbeknownst to them, the briefcase contains ransom money, and they're being tracked by criminals.

Their oblivion and mishaps create a whirlwind of comedic chaos, illuminating the humorous side of naïveté.

10. "There's Something About Mary" (1998)

Thirteen years after a disastrous prom date, Ted hires a private investigator to track down his high school crush, Mary. The investigator becomes smitten with Mary and lies to Ted about her. Eventually, Ted learns the truth and races to Miami to confess his feelings.

The film revolves around the domino effect of absurd situations resulting from multiple men falling for Mary's charm. Amid the laughter it sparks, the movie serves as a whimsical (although just a teensy wee bit problematic) reminder of the lengths some will go for love.