Almost all of them. I only ever win Monopoly because I steal half the board near the start. People assume it's a clever strategy but I'm really just a greedy bastard.
Provided that all players possess a relatively average degree of skill or the game is entirely luck based, any that require more than two players. Otherwise it depends on the game....
Any game that relies more on chance than skill. I have horrible luck in chance-driven games, especially if I try to play it smart. Life and Candyland especially hate me. With games that are pretty equally driven by luck and strategy, like Monopoly, I generally end up in the middle of the big winners and the poor losers. Whatever I'm doing to get those luxury taxes, I apparently love doing it...
Fun game but, frustrating as hell when you're losing.
Board games make me sleepy
Hmm, now I'm depressed.