15. Jesse James

Jesse James may not be such an obvious choice, but the fact that he’s average-looking at best, managed to score one of the hottest Hollywood’s leading ladies and then cheated on her and humiliated her in a very public way makes his one of the ugliest womanizers on our list.

After several women came forward with allegations of having had affairs with James during his marriage to Sandra Bullock, he publically apologized to the Oscar-winning actress, but the damage was already done.

He will forever be remembered as the mediocre, semi-famous dude who cheated on Sandra Bullock.

His other official conquests/ex-wives include Karla James, Janine Lindemulder, Melissa Smith, Brigitte Daguerre, Michelle McGee, Katherine von Drachenberg, and Alexis Dejoria.