4. First Daughter (2004) - Forest Whitaker's Teen Romance About The President's Daughter (Starring Katie Holmes)
Forest Whitaker, perhaps best known for his acting work, has directed a few terrible movies over the course of his career, but none of them are quite so bizarrely interesting as First Daughter, which is literally the movie you're picturing in your head right now, with Katie Holmes playing the title character. It's not surprising that a fun comedy movie about the president's daughter got made (it's been made loads of times, in fact - Chasing Liberty and My Date With The President's Daughter to name but two), but what, exactly, brought Mr. Whitaker to this project? I genuinely can't figure out how or why this man - who won an Oscar for his turn in The Last King of Scotland two years later - found himself giving directions to Katie Holmes in a Katie Holmes movie. They couldn't find some TV hack to do this one instead? What qualified Forest Whitaker to the point where he was genuinely considered as somebody who could pull this off? No matter: the movie was terrible, cliched and uninteresting in just about every way. But it's hard to imagine somebody more out of place in this scenario than ol' Forest Whitaker.