12. James Dean
James was famous on screen and off for writing motorcycles he scored his first motorcycle when he was only 15 years old, a 1947 CZ 125-CC. He was the only kid in his town to own one and rode it like a bat out of hell. After dropping out of college he traded the CZ in favor of a Royal Enfield 500 cc Vertical Twin which he subsequently traded for an Indian warrior TT that ended up in New York at a service shop where Steve McQueen was head mechanic. And that is how history was made. His last bike was a Triumph TR 5 Trophy.