Waylon Jennings admitted to having a $1,500 per day cocaine habit for much of his outlaw career. Many think the effects of the drugs followed him into sobriety and cut his life short in 2002 at the age of 64. In 1977, he was arrested for cocaine possession, but the charges were later dropped. He got a Top 5 hit called ‘Don’t You Think This Outlaw Bit’s Done Got Outta Hand' out of it. Jennings sobered up for good after moving to Arizona in 1984.