The 10 Best ’90s Comedy Movies

The 10 Best ’90s Comedy Movies

Gak, Pogs, Tamagotchi. No, that’s not a line from The Day the Earth Stood Still. They’re three toys that you may only recognize if you also know the difference between a Bop It and a Skip It. They were from the 1990s, a time of cultural significance in many ways. Who can forget when millions of people across America tuned in to watch Bob Dole starring in a Viagra commercial? Other news-worthy events include the release of Earthworm Jim and when the nation was caught up in the dance craze of Mambo No. 5. There were some other things that happened in the ’90s, but they’re not important.

It was a magical time when everyone wore jelly sandals while they drank Crystal Pepsi as they looked up the Spice Girls on Netscape. Phones couldn’t take pictures and MTV still kind of had to do with music. It also had some very funny movies. Grab your Waterworld and Robin Hood: Prince of Thieves action figures as we look at the funniest movies from the decade that introduced us to the star power of Pauly Shore and Baby Sinclair.

BASEketball (1998)

The often-overlooked wonderful blend of the Zucker brothers (Airplane!, The Naked Gun) and Trey Parker and Matt Stone (South Park, Orgazmo). Starring Parker and Stone as two losers who invent a new game which leads to international success, the humor is closer to their own personal style considering how much they improvised and wrote. You’ll never hear a better example of the usage of the word, “Dude.” Sometimes the radio knows exactly what you’re going through. It also answers the question of where you’ll find the most heinous, vile, and horrible exploitation of children on the planet. It co-stars Dian Bachar, Robert Vaughn, Yasmine Bleeth, Jenny McCarthy, and Ernest Borgnine. (Journey psych-outs are still off limits.)

The Big Lebowski (1998)

Easily one of the most quoted movies of all time, also one of the greatest detective movies ever made, the Coen brothers have made numerous wonderful movies, but this one may have the broadest audience. Jeff Bridges is “The Dude,” a man for his time and place. A case of mistaken identity and a carpet which really tied the room together are just the start for The Dude. John Goodman co-stars and rolls out what may be his funniest performance of all time as Walter Sobchak. This film bears repeated viewings. Pour yourself a “caucasian” and experience it, and if you don’t like it well…that’s just like, your opinion, man. Also, there’s Donny.

The Birdcage (1996)

Based on the French film La Cage aux Folles (1978), this farce concerns an openly gay couple who own a drag club in South Beach, and who’s son is getting married to a girl from an ultra-conservative family. To make matters worse, the family is coming to visit, and the son has told the family that his folks are straight. Against their wishes, the couple must play straight for the night, but nothing goes according to plan. Robin Williams, Nathan Lane, Gene Hackman, and Hank Azaria lead an all-star cast through this film. While it’s over-the-top and there are many jokes which could be considered stereotypical, Williams and Lane are endearing, believable, and funny. Even if you smear your mustard and walk like John Wayne, you’ll laugh at this movie.

Clerks (1994)

The breakout independent hit from writer/director Kevin Smith. It not only introduced the world to Jay and Silent Bob and the View-Askewniverse, but it also broke the mold of independent cinema up to that time. It stars Brian O’Halloran and Jeff Anderson as Dante and Randal, two corner store employees with big dreams and way too much time on their hands. It’s easy to see the influence of John Hughes in this movie, which Smith has directly referenced later in his career. It should also be noted that at the time of its release, it surprised critics and audiences with its offensive humor, but also impressed them with its heartfelt characters.

Dumb and Dumber (1994)

A chance encounter, lost jobs, and the sudden tragedy of their bird’s head falling off lead Lloyd (Jim Carrey) and Harry (Jeff Daniels) on a journey to Aspen, California for a chance at life and love. Another quotable favorite. This movie introduced the Farrelly brothers to the world. Daniels was initially not wanted for the role of Harry. Jim Carrey wanted Jeff Daniels because he wanted a good actor to play off of, not just another comedian. They’re silly, but the performances are so good, they make you really care about these two clowns. The funniest part of their stupidity is that they are both so confident and sure of what they’re saying, just like real idiots. Even stupid comedy needs to be played straight and honest.

Groundhog Day (1993)

This movie is so well-known and appreciated, it’s almost become its own genre. (Bing!) It’s already a Broadway musical. (Bing, Again!) But, the film itself is a gem. Phil Connors (Bill Murray) is stuck in Punxsutawney on Groundhog Day and for whatever reason must experience the same day on a loop. Questions of theology and existence quickly turn to downright shenanigans and beyond. Directed by Harold Ramis, it has one of the all-time best performances by Murray. Everyone who watches this movie will inevitably ask themselves, “What would YOU do?” This movie proves it’s never too early for flapjacks, and it’s never too late to make a change.

Office Space (1999)

Not necessarily a hit upon release, this film has since become a cult classic. Written and directed by Mike Judge, it’s about a man named Peter (Ron Livingston) and his buddies who are sick of their boss and their job and want to do something to change it. It proves that you don’t need a million dollars to do nothing. It answers the question: How much flair is the minimum amount? It shows that you can’t put a price on the value of happiness, or a red stapler. It’s not hard to see the connections between this movie and Judge’s current Silicon Valley. Mike Judge’s humor is always funny and sometimes way too real. If that’s the case, then Idiocracy should be terrifying.

Robin Hood: Men In Tights (1993)

No no, just…merry. It’s the classic romantic tale of Robin Hood (Cary Elwes) and Marian (Amy Yasbeck) and Robin’s merry men fighting back against Prince John (Richard Lewis) and The Sheriff of Rottingham (Roger Rees). Only, it’s directed by Mel Brooks so get ready to giggle. It’s also Dave Chappelle’s first film! Wonderful cameos are spread throughout. There are so many fantastically goofy moments in this, along with many of Brooks’ trademark jokes, asides, and one-liners. Richard Lewis’ performance as Prince John is one for the times. At least this Robin Hood can speak with an English accent.

Tommy Boy (1995)

The best parts of a buddy movie and an on-the-road movie. Tommy (Chris Farley) is out to save the family business with the help of his long-time friend Richard (David Spade). Farley’s physical comedy is amazing, and Spade’s sarcasm is the perfect opposite. Rob Lowe also gives a great, funny performance throughout. This, along with Black Sheep (1996), had sad moments in between the slapstick and crude humor, and showed just how good of an actor Farley actually was. If you learn anything from this movie, it’s that true friends are there for you no matter what, and that you always take the butcher’s word for it.

Wayne’s World (1992)

Party time. Excellent. One of the funniest and most memorable movies of the decade. Directed by Penelope Spheeris and starring Mike Myers and Dana Carvey as two young doofuses with their own cable access T.V. show. (This was before YouTube.) This movie introduced many young folks to rock ‘n’ roll, specifically the band, Queen. (To be fair to Queen, we all would have discovered them eventually.) This and the sequel are still funny even if you know when the jokes are coming. Let’s be honest, Mike Myers has been doing the same jokes his entire career, but these movies are him at his best. While it’s not the first SNL movie, this movie started the SNL movie craze where every reasonably successful character/sketch could be a potential flick. (Turns out, they really couldn’t).

Do you agree with this list? What films would you pick? Ah, what do you know from funny? Tell us in the comments below.