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When you first meet Dean Winchester, he seems a rather simple guy. Cocky, obnoxious, womanizer. Then you find out about his fierce loyalty to Sam. his father, and the people he saved. Dean loves hunting, the way his father does. Soon you find out about his fondness for children, and suddenly he’s a lot more likable. The main thing for Dean, I think, is the difference between how he acts and how  he is. Like why he got Sam from Stanford– he says it’s to help find Dad, but then he admits that he just wants them to be a family again.

He’s basically the same character up until the fourth season, when he comes back form hell. He’s starting to break, and when Sam accidentally starts the apocalypse, he shatters. Famine says it himself, he’s dead inside. (Dean throwing out the amulet Sam gave him had to be the worst thing he ever did. Grr.) He does regain hope, eventually, but…he’s never quite the same.

When Sam jumps, Dean becomes the family man. Even when he goes back to hunting with Sam, he’s the cautious one, the caring one, basically the good cop to Sam’s bad.

When Sam gets his soul back, Dean returns more to how he used to be, but now he’s more balanced, and actually cared about his own skin.