27 Hilarious Comedies That Prove the ’90s Was the Funniest Decade

I love ’90s music and films. It was the greatest decade. I’m torn between it and the ’70s. Nonetheless, the nineties produced numerous comedies that made it stand apart from the other decades. Here are my absolute favorites.

1. Wayne’s World (1992)

Wayne's World 1992
Image Credit: Paramount Pictures.

“Wayne’s World. Wayne’s World. Party time. Excellent! Based on the Saturday Night Live sketch Wayne’s World, the film stars Myers in his feature film debut as Wayne Campbell and Dana Carvey as Garth Algar.

The two are a pair of rock and heavy metal fans broadcasting a public-access TV show. There are many quotable lines and an incredible car scene singing “Bohemian Rhapsody.” “Excuse me. Do you have any Grey Poupon?” 

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

Austin Powers International Man of Mystery
Image Credit: New Line Cinema.

“Yeah, baby!” Austin Powers: International Man of Mystery was written and produced by Mike Myers, who also plays the roles of Austin Powers and his arch-nemesis, Dr. Evil. It parodies James Bond and 1960s pop culture. It has fun music, quotable lines, flamboyant characters, and plenty of hilarity ensues. It also stars Elizabeth Hurley, Seth Green, Robert Wagner, and Michael York.

3. Dumb and Dumber (1994)

Dumb and Dumber 1994
Image Credit: New Line Cinema.

“So, you’re saying there’s a chance?!” Dumb and Dumber is a Jim Carrey cult classic that is ridiculously dumb and, get this, dumber. Jeff Daniels costars in this buddy comedy following two dim-witted friends who set out on a cross-country trip to return a briefcase to the owner. Naturally, they don’t realize the owner left it as a ransom, and they get into all kinds of hilarious shenanigans.

4. Rush Hour (1998)

Rush Hour 1998
Image Credit: New Line Cinema.

Rush Hour stars Jackie Chan and Chris Tucker as mismatched police officers assigned to rescue a Chinese diplomat’s abducted daughter. With action-packed martial arts scenes and numerous quotable lines, this movie is a classic that spawned two more funny films.

5. Kindergarten Cop (1990)

Kindergarten Cop 1990
Image Credit: Imagine Entertainment.

“I’m the party pooper!” Arnold Schwarzenegger stars as tough police detective John Kimble, who is working undercover as a kindergarten teacher to locate the wife and child of drug dealer Cullen Crisp (Richard Tyson) living under assumed identities. Pamela Reed, Penelope Ann Miller, and Linda Hunt co-star.

6. The Cutting Edge (1992)

The Cutting Edge 1992
Image Credit: Metro-Goldwyn-Mayer.

“TOE PICK!” The Cutting Edge is an adorable and funny film that follows an Olympic ice hockey player (D. B. Sweeney) losing enough vision to bench him permanently from the game.

To get a pair of skates back on his feet and another chance at the Olympics, he pairs up with a spoiled figure skater (Moira Kelly) who can’t hold onto a partner for long with her attitude. Love blossoms, the skating is moving, and there are tons of laughs. It stars

7. Happy Gilmore (1996)

Happy Gilmore (1996)
Image Credit: Universal Pictures.

Happy Gilmore stars Adam Sandler as Happy, an unsuccessful hockey player who finds himself playing golf with the help of his coach, Chubbs (Carl Weathers). Grandma is going to lose her house to back taxes, so Happy sets out to make enough money to keep her house. It’s a classic ’90s comedy gem. “What? Friends skate to ‘Endless Love” in the dark?!” 

8. Sister Act (1992)

Sister Act
Image Credit: Touchstone Pictures.

Sister Act is a hilarious film where lounge singer Deloris Van Cartier (Whoopi Goldberg) witnesses a murder and is placed into witness protection, hiding in a convent. She uses her time there teaching the choir up to par while getting into many hilarious shenanigans. The cast and the music are fun. Sister Act 2: Back in the Habit is also a hilarious film. 

9. Six Days Seven Nights (1998)

Six Days Seven Nights 1998
Image Credit: Touchstone Pictures.

Six Days Seven Nights is an underrated ’90s comedy with action and adventure. Robin Monroe (Anne Heche), a New York magazine editor, and the drunken pilot Quinn Harris (Harrison Ford) are forced to put aside their mutual dislike if they are to survive after crash landing on a deserted island. David Schwimmer also stars for some extra laughs. 

10. Office Space (1999)

Office Space 1999
Image Credit: Judgemental Films.

Office Space is the gift that keeps on giving. The tech is outdated, but the general feel of what it’s like working in a cubicle remains the same. It follows three disgruntled computer programmers navigating layoffs and a get-rich scheme that goes awry. 

11. The Wedding Singer (1998)

The Wedding Singer
Image Credit: New Line Cinema.

The Wedding Singer follows a wedding singer (Adam Sandler) being stood up at the altar. He befriends a waitress (Drew Barrymore) who is getting married and helps her plan the wedding. The soundtrack is a trip back to Funkytown, and it’s full of quotable laughs. 

12. Captain Ron (1992)

Captain Ron
Image Credit: Buena Vista Pictures Distribution.

Captain Ron is one of the most hilarious movies of all time. It stars Kurt Russell in the titular role. After Martin Harvey (Martin Short) inherits a boat docked in the Caribbean, he uproots his family for a vacation and hires Captain Ron to navigate the ship to Miami. It doesn’t take long before Martin dislikes him, and the back-and-forth antics will have you bursting at your sides. 

13. Friday (1995)

Friday 1995
Image Credit: New Line Cinema.

Friday is a cult classic with many laughs. It follows Craig (Ice Cube) getting fired on his day off and his friend Smokey’s (Chris Tucker) ploy to get him to try weed. It’s filled with eccentric characters, good music, and quotable lines.

14. What About Bob (1991)

What About Bob Swimming
Image Credit: Tombstone Pictures.

What About Bob is another cult classic that follows obsessive-compulsive neurotic Bob (Bill Murray), following his psychotherapist Dr. Leo Marvin (Richard Dreyfuss), and his family on their family vacation. Bob gets close to Dr. Marvin’s family while driving him to the brink of madness in this black comedy.

15. Conspiracy Theory (1997)

Conspiracy Theory1997
Image Credit: Warner Bros.

An underrated 90s film that’s not a comedy but has plenty of laughs, Conspiracy Theory follows a taxi driver (Mel Gibson), an avid believer of conspiracy theories, and his obsession with a Justice Department attorney (Julia Roberts). One of his conspiracy theories proves true, and they have to navigate the truth to save his life. 

16. Tremors (1990)

Image Credit: Universal Pictures.

Tremors is one of the best horror comedies of all time. Two handymen (Kevin Bacon and Fred Ward) decide to leave their middle-of-nowhere town when they encounter creatures pulling people underneath the ground—the small town band together to survive while delivering plenty of laughs. It also stars Reba McEntire and Michael Gross. 

17. Teenage Mutant Ninja Turtles II: The Secret of the Ooze (1991)

Teenage Mutant Ninja Turtles II1991
Image Credit: New Line Cinema.

Teenage Mutant Ninja Turtles II: The Secret of the Ooze is an example of a sequel surpassing the original. Leonardo, Donatello, Michaelangelo, and Raphael search for a new place to live while battling the foot clan and the elusive Shredder. This film also spawned the Ninja Rap — “Go ninja, go ninja go!” 

18. True Lies (1994)

True Lies 1994
Image Credit: 20th Century Fox.

True Lies follows a fearless secret agent (Arnold Schwarzenegger) and his humorous partner (Tom Arnold) working to defeat terrorists in the States. After he believes his wife (Jamie Lee Curtis) is having an affair with a used car salesman, he unwittingly pulls her into danger, and they must fight to survive together. 

19. Romy and Michele’s High School Reunion (1997)

Romy and Michele's High School Reunion
Image Credit: Touchstone Pictures.

“Have a Romy and Michele day!” Romy and Michele’s High School Reunion is stupidly funny. It follows two dim-witted, inseparable friends (Lisa Kudrow and Mira Sorvino) hitting the road for their ten-year high school reunion. They devise an elaborate lie to tell at the reunion to impress the mean girls, but it does not go according to plan. Janeane Garofalo will have you splitting at your sides. 

20. Major League II (1994)

Major League II 1994
Image Credit: Warner Bros.

Nothing beats the original 1989 Major League classic is funny, but the sequel comes close. The Cleveland Indian’s baseball team is a World Series contender and has to fight to achieve the impossible of staying together when the new manager is doing everything they can to tear the team apart. 

21. Addams Family Values (1993)

Addams Family Values 1993
Image Credit: Paramount Pictures.

Addams Family Values is a classic example of the sequel surpassing the original. The addition of Joan Cusack’s character, Debbie Jellinsky, a black widow serial killer who marries Fester Addams (Christopher Lloyd), intending to murder him for his inheritance, is an unforgettable performance. Wednesday (Christina Ricci) and Pugsley (Jimmy Workman) at summer camp deliver barrels of laughter.

22. Demolition Man (1993)

Demolition Man 1993
Image Credit: Warner Bros.

Demolition Man is an action-packed story in a dystopian future where Taco Bell is fine dining, and all weaponry is behind glass in a museum—a criminal (Wesley Snipes) who was cryogenically frozen escapes during a parole hearing.

So the police force of 2032 thaws a risk-taking police officer (Sylvester Stallone) to help get the situation under control. Sandra Bullock is adorable, but we never learn how to use the three seashells.

23. Son in Law (1993)

Son in Law 1993
Image Credit: Hollywood Pictures.

Everyone remembers the genius that is Encino Man, but many forget about the hilarity that ensues in Son in Law. Pauly Shore plays Crawl, a flamboyant college resident advisor who helps a country girl from South Dakota (Carla Gugino) come out of her shell and embrace California culture. When she takes Crawl home to the farm for the holidays, a series of events provide plenty of chuckles. 

24. Death Becomes Her (1992)

Death Becomes Her 1992
Image Credit: Universal Pictures.

Death Becomes Her is a black comedy about immortality. Best friends Helen (Goldie Hawn) and Madeline (Meryl Streep) part ways when Madeline steals Helen’s fiancé, Dr. Ernest Menville (Bruce Willis). Years later, when Helen shows up for revenge, a magic potion that gives immortality comes into play. But it has unpleasant side effects that prove chucklesome.

25. Grumpy Old Men (1993)

Grumpy Old Men 1993
Image Credit: Warner Bros.

Grumpy Old Men is a sidesplitting back-and-forth between two retirees, neighbors, and friends. John Gustafson (Jack Lemmon) and Max Goldman (Walter Matthau) exchange insults and play pranks on each other as part of their routine.

When a new neighbor (Ann-Margret) moves in and captures their attention, the gloves come off, and the real laughter begins. The sequel, Grumpier Old Men, is equally funny. 

26. L.A. Story (1991)

L.A. Story 1991
Image Credit: Tri-Star Pictures.

This underrated 90s comedy film delivers buckets of chuckles. It follows a weatherman (Steve Martin) who uses the help of a talking freeway billboard to try to win the heart of an English newspaper reporter (Victoria Tennant). The story is unique and includes a young Sarah Jessica Parker as a fun and ditzy spokesperson whom he also dates.

27. My Cousin Vinny (1992)

Marisa Tomei
Image Credit: 20th Century Fox.

My Cousin Vinny is a 90s comedic gem. It tells the story of two New Yorkers (Ralph Macchio and Mitchell Whitfield) accused of murder in rural Alabama while on their way back to college.

They call in the help of one of their cousins, Vinny (Joe Pesci), a loudmouth lawyer with no trial experience, and a beautifully charming fiancée, Mona Lisa Vito (Marisa Tomei). This film is laughter from start to finish. 

26 Comedy Films That Cancel Culture Forbids You From Laughing at Today

Revenge of the Nerds
Image Credit: 20th Century Fox.

Has cancel culture come for your favorite films? There are several classic comedies that were once considered hilarious that are deemed offensive today. Here are twenty-six of them.

25 Nostalgic Movies Everyone Needs to See at Least Once in Their Lifetime

One Flew Over the Cuckoo's Nest
Image Credit: United Artists.

Take a trip down memory lane with this hand-picked list of classic films that have forever changed the face of cinema. These movies represent the spirit of different times and genres, from inspiring stories of friendship and adventure to terrifying suspense and beautiful romance.

12 Plot Points That Popular Movies Didn’t Bother Resolving for Audiences

The Karate Kid 1984 Daniel and Ali
Image Credit: Columbia Pictures.

Do any of your favorite films have plot holes that were never resolved? You’re not alone. An entertainment community poster asked for examples of said plot holes. Here is what the forum volunteered. Did you notice?

Top 25 Longest Movies of All Time — Worthy of Every Minute

Image Credit: MGM.

Some stories in the world of film need more time to reveal their beauty. This collection recognizes the longest films that have captured our attention, hearts, and imagination. They range from epic sagas to deep dramas. Enter a universe where time is infinite as we watch movies that show that every second is a journey worth going on.

15 Famous Songs That Music Fans Voted as the Saddest — Do You Agree?

Fleetwood Mac
Image Credit: Shutterstock.

What is the saddest song you’ve ever heard? I’ll go first. Powfu’s song “Death Bed (Coffee for Your Head)” will hit you right in the feelings. After someone polled a music forum for other examples of the saddest songs of all time, here are THEIR top-voted songs. Do you agree?

 

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Elizabeth Ervin is the owner of Sober Healing. She is a freelance writer passionate about opioid recovery and has celebrated breaking free since 09-27-2013. She advocates for mental health awareness and encourages others to embrace healing, recovery, and Jesus.