Known for such southern rap albums as Portrait of a White Boy, The New South, and Crackavelli, this artist released his debut album, Mak Million, in 1998. Between the late 1990s and the middle of the 2010s, he recorded more than twenty other albums and mixtapes.
In his mid teens, after being incarcerated for possession of illegal drugs, he turned to music as an escape from a life of crime.
He and fellow Tennessee-born rapper JellyRoll (Jason DeFord) collaborated on two early 2000s albums: Strictly Business and Business as Usual.
Born Jason Winfree to a teenage mother, he was raised in Lebanon, Tennessee by his grandparents. He and his wife later became parents to two children.
He and fellow artist Bubba Sparxxx (Warren Mathis) both became known for their work in the southern rap genre.