21. James Dean
Notable Roles: Rebel Without a Cause (1955); East of Eden (1955); Giant (1956)
The broody cult favorite, America's rebel fondness for speed is likely what ended his life so early into his career. Dean was able to gain his iconic status in a few short years after starring in just three films. Outfitted in a red jacket, white t-shirt and blue jeans in Rebel Without a Cause, he made his mark in history and influenced generations to come, including Michael Bastian's spring 2012 collection.