10 Iconic 2000s Comedies That Aren’t Funny Anymore

The glorious 2000s gave us certified classics like Anchorman, Superbad, and Mean Girls, but for every gem, the decade also served up a full course of crappy comedies that should never have been made. These films lean on tired premises, confuse “offensive” with “edgy,” worship pop-culture references like golden calves, or just forget what a joke is.

If you’ve ever wondered why your rewatch turned into a guessing game of “Why am I watching this?”, here’s the hall of womp-womp fame.

Dumb and Dumberer: When Harry Met Lloyd (2003)

Who would have guessed that prequels can be unsatisfactory, and that casting two C-class actors couldn’t replicate the chemistry of Jim Carrey and Jeff Daniels? This high-school origin story delivers a tragic lesson: the original Dumb and Dumber wasn’t just silly—it was lightning in a bottle. Without the leads’ top-notch facial expressions and perfect comedic timing, you’re left with a “huh” and a “whuh.” It’s the cinematic equivalent of a deflated fart cushion.