59. Fredo Corleone
played by John Cazale in The Godfather Part II
Anyone who failed to turn out the way his or her parents would have liked should have some sympathy for Fredo. He doesn’t even get the chance to disappoint his family because they have so little invested in him to begin with. Not only is he not worthy of disappointment, it turns out he’s also not worthy of that most familial of gestures, forgiveness.