Born Jason Winfree in Nashville, TN, to teenage parents and raised by his grandparents, Haystak grew up among impoverished surroundings. He turned to crime as he came of age, ultimately getting busted for bringing Valium and cocaine to school at age 15. After serving a two-year sentence, Haystak turned to rap music as his salvation. Initially known best for being a huge white-boy rapper from Tennessee, Haystak overcame his anomalous status with time as listeners learned to cherish his sincerity. Unlike many of his Southern peers, Haystak did not embrace materialism and greed; he rapped about his life as so-called "white trash," exploring the social dimensions of being white and underprivileged in the South. Few gave the mammoth country boy a chance to succeed, however.