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Love Comedy??! Have You Watched These Late 90s/Early 2000s Hollywood Comedy Movies?

By Princess Okwudili 4 Min Read
Adam Sandler in happy Gilmore

If you love to laugh, then you can’t miss these classic comedies from the late 90s and early 2000s! From over the top gags to unforgettable one liners, these movies are the best when it comes to non-stop laughter. Let’s take a quick look at some of the funniest films from that era.

1. Dumb and Dumber (1994)

Jim Carrey and Jeff Daniels are the ultimate odd couple as two dim-witted friends who stumble into crazy situations. With Carrey’s exaggerated expressions and Daniels’ perfect deadpan humor, their adventure becomes a hilarious series of misunderstandings. Dumb and Dumber remains one of the best comedies ever made.

2. Legally Blonde (2001)

Reese Witherspoon shines as Elle Woods, delivering humor and empowerment. The combination of quirky humor and heart made this movie a classic. When her boyfriend dumps her, Elle decides to prove him wrong by heading to Harvard Law School. With her signature style and charm, she turns the stuffy world of law upside down.

3. American Pie (1999)

Following a group of friends trying to make a pact before prom, American Pie is packed with cringe-worthy situations and over-the-top scenes that range from awkward to funny. The hilarious characters and infamous scenes keep it a comedy staple.

4. White Chicks (2004)

Shawn and Marlon Wayans go undercover as wealthy white women in this absurd, laugh-out-loud comedy. It’s still one of the most quotable movies of the 2000s. White Chicks is absurd, ridiculous, and full of those “did that just happen?” moments that make it endlessly entertaining.

5. Scary Movie (2000)

A parody of the horror genre, Scary Movie turns famous horror films into wild comedy. The Wayans brothers’ clever humor and over the top characters like Cindy Campbell and Brenda, makes this one a must-watch.

6. The Waterboy (1998)

Adam Sandler delivers one of his funniest performances as Bobby Boucher, a socially awkward waterboy who surprises everyone with his hidden talent for tackling. His journey from team waterboy to football hero is both funny and heartwarming, with Sandler’s character delivering iconic lines like “You can do it!” It’s your classic underdog story, but with Sandler’s goofy humor.

7. Happy Gilmore (1996)

This is another Adam Sandler comedy about a failed hockey player trying to make it in golf is packed with funny moments. From Happy’s antics to his hilarious golf course behavior, this movie never gets old.

Why do they Still Make Us Laugh?

These movies, weren’t afraid to embrace awkwardness, and deliver humor that is both absurd and relatable. They didn’t just provide laughs, they gave us unforgettable characters, unforgettable quotes, and memorable moments that still hold up today. If you haven’t watched them, it’s time to visit these comedy classics and if you have, it’s time to revisit them. These movies will have you laughing nonstop. Go ahead and check your favorite streaming platform, press play and enjoy!

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