Pitt is at his best when he can use his natural charm. Even as a straight male, theres no denying hes an incredibly good looking dude so he always crushes those types of roles. He doesnt play the loser type of part well. But He can play unhinged, crazy, but theres always a loveable endearing layer to it. I actually think one of his best roles was the only time he played a villain: Kalifornia. Movie itself was meh, but thought he was really good. Would love to see him take on more of those kind of roles