Conor Oberst (Bright Eyes)

Most hear the name and associate him with his 17 year old incredibly emo self, with lyrics that sound like you're reading from an angsty teenage diary.

The guy grew up and it's reflected in every one of his albums. Was about as good as an angsty 17 year old could be as a sad emo singer, and became about as good as you can be as a 40 year old folk singer and everything he's done in between.