3. Drew Baylor - Elizabethtown
Cameron Crowe's second film on this list is a little more obscure, not in the sense that less people know of it, but more that its nowhere near as universally lovable as his debut. "Elizabethtown" is chock full of very strange character moments and a confusing tone. Drew Baylor is at rock bottom and about to commit suicide in the most ridiculous and horrific way when he is informed of his father's death. His sister pleads him to come take control of things, so he pauses his torture-device suicide to fly to Kentucky. On this flight he meets Claire, who one might say (as in Wikipedia does say) is "energetic, charming and knows how to read people." She serves as the consistent bright light at the end of Drew's dark tunnel throughout the whole film until she ultimately cures him of his Clive Barker death fantasies with a mix CD and a kiss. I was going to write about Claire being the inherently insane character in this film, but she is really just a wooden version of the whole manic pixie dream girl outline. Drew is the one who goes from near celebrity status (as a shoe designer?) to stationary knife-bike constructor to "fixed". Lloyd Dobler might be a potential case of crazy, but Baylor is insane, maybe even dangerous.