4. Tim Allen
He seems like a really nice guy, right? But before he become famous Tim was a coke dealer. On October 1978 he was caught at the Kalamazoo International Airport, transporting over 650 grams of cocaine. In exchange for not having to go to prison for his whole life, Allen pleads guilty and ratted out the other drug dealers he knew. He ended up serving 28 months in a Federal Correctional Institution in Minnesota.