10 Iconic 2000s Comedies That Aren’t Funny Anymore (3 of 6)

Kangaroo Jack (2003)

Marketed as a goofy talking-animal romp, this movie did the cinematic equivalent of catfishing. Remember the rapping kangaroo clip in the trailer? That’s basically a dream sequence. The plot is actually about two knuckleheads running cash for the mob in Australia, only to lose it to a very normal, non-chatty marsupial. It’s like ordering a pizza and getting a boring old celery stick instead.

Pledge This (2006)

A National Lampoon badge used to mean something. Here, it’s pasted onto a sorority comedy whose main innovation is “What if everything was shinier?” Paris Hilton stars as the queen bee on a quest for “Best Sorority” glory, while recruits endure hazing so cartoonish it feels like a parody of a parody. None of the jokes land, there’s no plot, and the whole thing feels like an extended reality-TV B-roll.