I haven't voted for the winning Presidential candidate since 1992. Several times during my losing streak I held my nose and voted for the "lesser of two evils" and at least once I voted for a 3rd party candidate, but none of them worked out.
In '92 I voted for a young guy who didn't have a lot of experience, but he was charismatic and said all the right things about leaving the old ways of Washington behind. He was also wrapped in the mantle of JFK, and had a cool photo of himself meeting the great man in the Rose Garden when the lad was just 16. He had a strong and accomplished wife -- a successful corporate lawyer with an Ivy league pedigree to match her husband's. I found this guy very inspiring and voted for him with enthusiasm. Once.
I think this is part of why I'm having a hard time jumping on the Obama band wagon. I find these parallels a little spooky, and like a badly jilted lover, I don't want to be disappointed again by misplaced faith in an articulate do-nothing.