The 10 Funniest 90s Comedy Movies, Ranked

The 90s had so many good comedies, we could have made this the Top 100 films… but we needed to draw the line somewhere. Here are the highlights of comedy from the 1990s.

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Maybe it’s just because I grew up in the 90s, but the decade was just so incredible for comedy films. Literally hundreds of hilarious movies came out in the 1990s. Whether you like some heavier comedy or straight-up slapstick, there were movies released in the 90s for you.

The fact that the decade was so strong in terms of comedy means we have to go and pick the 10 funnies movies from the era and put them in order. This isn’t the best necessarily, but rather which ones make us laugh the most.

It’s no easy task, but it’s one we’re willing to undertake for the love of all things funny.

10. Office Space

Office Space is 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 of Office Space’s motley 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.

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9. Don’t Be A Menace To South Central While Drinking Your Juice In The Hood

Don’t Be A Menace To South Central While Drinking Your Juice In The Hood is 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.

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8. Dumb and Dumber

Jim Carey and Jeff Daniels were the perfect actors to play Harry and Lloyd in the original Dumb 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, then Dumb and Dumber is probably already one of your favorite movies.

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7. Friday

Friday is 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.

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6. Happy Gilmore

If you’re a fan of comedy, I probably don’t need to tell you just how good Happy Gilmore is. 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 seeing Happy Gilmore, then do yourself and favor and watch it immediately.

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5. My Cousin Vinny

It’s impossible to dislike My Cousin Vinny. Coming hot off the heels of Home Alone, Joe Pesci flexed his comedic muscles in this absolute classic. My Cousin Vinny has 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.

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4. Billy Madison

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.

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3. Ace Ventura: Pet Detective

While Adam Sandler may have had the best two-year period, Jim Carey had both Dumb and Dumber and Ace Ventura: Pet Detective come out in the same year. Two of the ten 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.

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2. Clerks

1994 was a killer year. Not only did it have several movies we mentioned so far, but it had Kevin Smith’s masterpiece known as Clerks. Here’s where we first met beloved character Jay and Silent Bob (Bob is actually played by Smith himself). Clerks is 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.

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1. Tommy Boy

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. Check out our ranking of every hilarious Chris Farley movie ever made!

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