For as different as their lives wound up turning out, both Charlie Sheen and Ashton Kutcher had similar problems early on. Sheen was thrown out of high school for poor attendance and grades, which spurred him to follow his passion for acting. And Kutcher was arrested during high school for theft and later expelled from his college apartment for partying too hard. He would later drop out of college altogether after he found success as a model.
In the showbiz world, the Kutcher family name ends with Ashton, but the Sheen/Estevez legacy is one of the more hallowed ones in Hollywood. His father, Martin, is one of the film world's all-time great actors; to be specific, he was the star of Apocalypse Now, the best war movie ever produced. Even Charlie's brother, Emilio Estevez, became a household name after starring in the Mighty Ducks trilogy.
Sorry, Ashton, but you can’t compete with old man Martin Sheen, or the legacy of The Mighty Ducks franchise.
The edge goes to: Charlie Sheen