9. Lindsay Lohan - The Hangover
This generation's Courtney Love was up for the role of Jade in The Hangover, but she rejected the project because she didn't believe that it had the potential to succeed. While this isn't necessarily a terrible reason to turn down a role, it comes off as a little too picky for someone who doesn't exactly have offers pouring in all the time. After all, beggars can't be choosers. The film went on to be a box office hit, spawning two sequels and single-handedly launching Mike Tyson's acting career. Had she accepted the project, it could have been that one role that launched her back into the realm of credibility as an actor. But what am I saying? That would just be the smart thing to do.