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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 didn't 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. Following the success of fellow white-boy rappers Eminem and Bubba Sparxxx, Haystak found it easier to earn respect in an industry that had long frowned upon white rappers, particularly those from the country.
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. Few gave the mammoth country boy a chance to succeed, however. In the late '90s he defied the odds by aligning himself with a local rap label, Street Flavor, and producers Kevin Grisham and Sonny Paradise. The partnership resulted in Mak Million, Haystak's 1998 debut album, followed two years later by Car Fulla White Boys. By this point Haystak had garnered a substantial regional following, and underground hardcore rap publication Murder Dog especially championed the blossoming rapper. The ensuing buzz attracted Koch Records, who signed Haystak and re-released Car Fulla White Boys in late summer 2000. Two years later, Koch released Haystak's third album, The Natural.