44. Jack Kerouac
Jack Kerouac was a novelist of the early 20th Century who definitely had a “James Dean” thing going on. Beautiful as well as intelligent, he was a novelist as well as a poet, pioneering the Beat Generation. He wrote spontaneous prose covering many topics, ranging from travel to jazz to drugs and poverty. He’s considered the inspiration for the famous people of the 1960s, including the Doors, the Beatles, and Bob Dylan. He played fast and loose with his words and life, as he was known for being a heavy drinker. A shame that he couldn’t have taken a healthier approach so that he could have graced us with more of his face and work.