8 – There’s Something About Mary – Though Ben Stiller and Cameron Diaz had enjoyed modest success in Jim Carey movies like The Cable Guy and The Mask, it wasn’t until they teamed up in the Farrelly Brothers’ gross out comedy, There’s Something About Mary that their careers really took off. Diaz plays the gorgeous Mary and she quickly becomes the object of affection for every guy in the film, including Stiller’s character Ted and an in-his-prime Brett Favre. There’s Something About Mary also revitalized Matt Dillon’s career, and he is spot on as the creepy private investigator Healy. Though the movie is filled with plenty of crude humor, and may offend the delicate sensibilities of some viewers for me it is a no-brainer as one of the top 10 funniest movies of the 90s.
7 – Kingpin – Speaking of gross out comedies, Kingpin is another Farrelly Brothers vehicle that will have the people in the audience howling despite their revulsion. Woody Harrelson plays Roy Munson, whose tremendous bowling ability is snuffed out when a showdown with rival Ernie McCracken leaves Roy with a hook instead of a hand. In an effort to get back to the top any way he can, Munson rides the coattails of a young Quaker bowling prodigy, played by Randy Quaid, back to the top. The movie has too many classic lines to quote, and the “arrangement” Munson has with his landlady will have you shuddering long after the final credits roll.
6 – Swingers – When discussing movies that are the most quotable of all time, this Vince Vaughn, Jon Favreau that seemed to come out of nowhere has to be at or near the top of the list. Lines like “You’re so money and you don’t even know it” and “You always double down on 11” have become a part of pop culture and are still referenced today. Being a Canadian I particularly like the the scene where they are playing NHL 93 and Vaughn makes Gretzky’s head bleed. One of the best comedy films of the 90s and one that I make a point of watching at least once a year.
5 – Office Space – Long before the comedy TV series The Office became a major hit, there was a little movie that brightened the lives of anyone who had ever worked in an office. Disgruntled employees finally decide they’ve had enough and plant a computer virus to embezzle money from the company. Gary Cole really steals the show as Bill Lunbergh, and his quotes from the film are some of the most memorable in recent movie history. Though it might not have made a mint at the box office this movie has a huge cult following, and is certainly more popular today than it was at the time of its 1999 release.
4 – Nothing To Lose – Martin Lawrence has turned in a lot of borderline performances in his comedy career, but this hilarious film that has him starring opposite the versatile Tim Robbins was not one of them, and was one of the funniest movies of the 90s. Lawrence plays Terrance Davidson, a down on his luck computer expert who can’t get a job, and in desperation finally turns to a life of crime. Robbins plays Nick Beam, a successful ad exec whose life is turned upside down when he thinks he’s caught his wife cheating on him. The movie takes off when Terrance attempts to rob Nick, and Nick, feeling he has nothing to lose, turns the tables. Together, these two ‘desperate’ men eventually team up and pull off a big heist. The movie is chock full of funny dialog and some well done slapstick humor. Not many people saw this movie when it was released back in 1997. If you were one of those that didn’t I recommend you rectify the situation as soon as possible.
3 – Dumb and Dumber – Much like Mike Myers, In Living Color alum Jim Carey was one of the biggest draws in Hollywood in the 90s, starring in comedy smashes like Ace Ventura: Pet Detective, The Mask, The Cable Guy, and Liar Liar. Any of those movies would not looked out of place of a list of the top 10 funniest movies of the 90s, but in my humble opinion it was the goofy comedy Dumb and Dumber that really sticks out as the gold standard of Jim Carrey’s comedy film career. Jeff Daniels shows a surprising penchant for comedy, and sparkles as Harry Dunne, best friend to Carrey’s Lloyd Christmas. The pair are indescribably stupid and get themselves in all sorts of trouble throughout the movie, including making an enemy of a very intimidating redneck named Sea Bass, played by ex hockey player Cam Neely. Dumb and Dumber, as the name implies, certainly won’t stimulate your cerebral cortex, but if you are in the mood to laugh at some stupid humor then you would be hard pressed to find a better choice than this classic comedy film.
2 – American Pie – There are so many average teen comedy films out there that I really didn’t expect too much when I went to see this movie in the theater back in 1999. Never have my expectations been so completely exceeded as they were by this film. I was laughing so hard I was crying through much of this movie, and I certainly wasn’t alone. Stifler alone was worth the price of admission. Sure the acting wasn’t the greatest. Seann William Scott and Eugene Levy might have been the film’s most talented actors. Not hard when you are competing against Tara Reid, Jason Biggs and Shannon Elizabeth. Yet, something about the movie just struck a chord. The characters seemed genuine, and every single one of them had decent comedic timing. At the time I wasn’t so far removed from high school that I couldn’t identify with the situations the characters found themselves in. Several sequels have since appeared, but the series has gotten progressively worse, and if you haven’t seen any of the movies then don’t waste your time with any but the original American Pie.
1 – The Big Lebowski – Though I’m not sure the Coen Brothers actually intended this movie to be a comedy, the dialog and the situational comedy throughout this film is so good that I have no choice but to name it to the number one spot on my list of the top 10 funniest movies of the 90s. Jeff Lebowski, Walter Sobchak, Donny Kerabatsos, and Jesus Quintana all deliver the laughs in this hilarious movie about a case of mistaken identity. Quotes abound in the film, and if you pull one out a party you can be sure to get a reaction from multiple Lebowski fans. The movie, which was the Coens’ follow-up to their Oscar award winning Fargo, was panned by critics, and flopped at the box office. However, as time passed the film became more and more popular, and now has a huge cult following.
So there you have it, the funniest movies of the 90s. Though studios were a little more shy than they were in the 80s when it came to releasing comedy movies plenty of classic funny films still made their way to theaters in the 90s.
Don’t see your favorite on the list? Here are a few honorable mentions: Rush Hour (Jackie Chan and Chris Tucker), Wayne’s World (Mike Myers, Dana Carvey), Ace Ventura: Pet Detective (Jim Carrey), Groundhog Day (Bill Murray), The Birdcage (Robin Williams and Nathan Lane).