Q. Have you ever wanted a villain to win at the end of a story? If so, which one?
I honestly don't know if I have ever rooted for a villain. If I ever have, it would be because:
A: The hero is bad. Whether it's because s/he is to Mary Sue/Gary Stu, or a total snob, or the author just didn't write him/her to well.
B: I feel bad for the villain. Maybe because s/he became a villain due to some deeply scarring back story (Phineas and Ferb, anyone;)), or the villain is still good but sort of persuaded to become evil.
Ooh, ooh, ooh! Writing that made me think of two cases! One: PERCY JACKSON AND THE OLYMPIANS. When Luke starts to regain control of his body when he has Kronos in him, I want so much for him to be the good guy (of course, Percabeth must prevail!).
Two: Okay, this one isn't a book, but a movie. Who, when watching the last STAR WARS (technically the third one made, but still the last in the saga) doesn't want Darth Vader to be good? Is it just me? Am I the only STAR WARS lover here?