It's a strange transition from the foul-mouthed comedies of Kevin Smith to Alvin and the Chipmunks, but Jason Lee made it. The skateboarder-turned-actor first came to fame in Mallrats and Chasing Amy and had some success in the early '00s, but it wasn't long before he was seized by the kid movie ghetto. The turning point came with 2007's Underdog, where he voiced the titular computer-animated superhero canine. From there, it was a short hop to three Alvin and the Chipmunks movies and the ruination of a career.