I love Crossroads because it's so terrible. Definitely one of the best "worst movies" I've ever seen, it tells the story of how Britney Spears looks like a fashion model and acts like an angel while still managing to be the most unpopular girl at school. Sob, sob! Incredibly awful and idiotic drama coupled with sickeningly sweet romance make this one a not-to-be-missed...if you're the sort to love MST3K, that is. Sure, Britney can't act too well, but she can sing, and this movie is actually a LOT better than Glitter, Mariah Carey's similarly-themed vehicle. (And by "better", I mean "less boring and self-indulgent.") It's been two years since I saw Crossroads and I still remember it vividly. It's a cult classic--moronic, worthless, contrived, and hilariously awful.
Review of Crossroads
