10. Office Space (1999)
Office Spaceis one of those comedies that’s always relevant—anyone who’s spent substantial time working in an office setting has probably encountered coworkers who fit into the archetypes ofOffice Space’smotley crew.
From the terrible boss to the weird members of the crew, we’ve all been there at some point. That makes this movie repeatable and hilarious.
Related:The Best Movies About Jobs, Offices, and Work
9. Don’t Be a Menace to South Central While Drinking Your Juice in the Hood (1996)
Don’t Be a Menace to South Central While Drinking Your Juice in the Hoodis one of the most underrated comedies ever released. It doesn’t get the same level of praise as some of the other classics we’re going to talk about today, but it absolutely should.
Shawn and Marlon Wayans created many hilarious movies over their careers, but this one stands on its own as one of the funniest.
Related:The Best Hood Movies That Are More Than Urban Stereotypes
8. Dumb and Dumber (1994)
Jim Carey and Jeff Daniels were the perfect actors to play Harry and Lloyd in the originalDumb and Dumber. The movie is ridiculous and might be a little too goofy for some.
But if you’re not turned off by completely over-the-top, well, everything, thenDumb and Dumberis probably already one of your favorite movies.
Related:The Dumbest Movie Characters Who Are Still Lovable
7. Friday (1995)
Fridayis a movie about a couple of friends just trying to get by. Of course, their lives are anything but ordinary, as they manage to find themselves knee deep in some comical situations.
Between Ice Cube’s relatively straight man performance to Chris Tucker’s general insanity, the movie brings a wealth of funny moments to the screen.
Related:The Best Movies About Stoners and Potheads, Ranked
6. Happy Gilmore (1996)
If you’re a fan of comedy, I probably don’t need to tell you just how goodHappy Gilmoreis.
Adam Sandler was truly in his prime when he stared in this tale of terrible-hockey-player-turned-incredible-golfer. But it’s not just Sandler who makes this film so great; the entire cast all plays an important part, and they all deliver big time.
If you somehow have made it through like without seeingHappy Gilmore, then do yourself and favor and watch it immediately.
Related:The Best Comedy Sports Movies of All Time, Ranked
5. My Cousin Vinny (1992)
It’s impossible to dislikeMy Cousin Vinny. Coming hot off the heels of Home Alone, Joe Pesci flexed his comedic muscles in this absolute classic.
My Cousin Vinnyhas tons of quotable funny moments, and it also has tons of emotional scenes. The contrast between the genuine consequences of the plot mixed with the ridiculous nature of Vinny Gambini truly makes for a special film.
Related:The Best Courtroom Drama Movies of All Time, Ranked
4. Billy Madison (1995)
As if you talk about 90s comedies without having more than one Adam Sandler film. 1995 and 1996 may have been the two best years for any comedic actor.
Sandler kicked things off with the tale of Billy Madison, an adult who needs to go through all of the school grades to inherit his father’s company. He followed that up with the aforementioned golf-comedy masterpiece. You’d have a hard time finding a better two-year period for anyone in comedy!
3. Ace Ventura: Pet Detective (1994)
While Adam Sandler may have had the best two-year period, Jim Carrey had bothDumb and DumberandAce Ventura: Pet Detectivecome out in the same year.
Two of the funniest movies of the decade both came out in 1994, and both stared the same person. If that’s not an impressive comedic feat, I don’t know what is.
Related:Iconic Actors Who Always Play the Same Roles in Movies
2. Clerks (1994)
1994 was a killer year. Not only did it have several movies we mentioned so far, but it had Kevin Smith’s masterpiece known asClerks. Here’s where we first met beloved character Jay and Silent Bob (Bob is actually played by Smith himself).
Clerksis a simple movie about a couple of guys who work in adjoining stores, but Smith finds a way to turn the basic plot into so much more.
Related:The Best Chill Movies That Feel Like a Hangout
1. Tommy Boy (1995)
As if there was any doubt, the funniest movie in the 1990s is Tommy Boy. Chris Farley, who is the funniest movie comedian to ever walk the planet, was at his best in this film.
David Spade plays a perfect straight man while Farley ramps everything up to the level of insanity that few other actors could achieve or even get away with.
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