Vincent van Gogh
Van Gogh wore many straw hats, and his short life was full of insane contradictions. He wanted desperately to be a pious priest, but fell deeply in love with an alcoholic prostitute. Some thought he was a genius, and others knew him to be a madman (both were correct). But his utter lack of self-cohesion is precisely what makes his artwork so stunning and beloved.
Van Gogh clearly suffered from severe mental illness, and after bouts of mania, he ended his own life at age 37. It wasn't long after his suicide, however, that his work began to gain a wider audience, and he eventually came to be regarded as one of the most groundbreaking artists of all time. In an excruciating turn, not unlike Kafka's burning of his own work, van Gogh's mother threw away dozens of her son's paintings, thinking them worthless. So if you ever get a time machine, be sure to visit her garbage can to collect the millions of dollars of artwork piled up there.