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.
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.
Haystak released his latest solo album entitled Easy 2 Hate on November 30, 2010 through Haystak, Inc. Haystak is married and has two children. In addition to rap music, he embarked on an acting career; he was featured in the documentary White Boyz Can't Rap and the film Hustle & Flow where he played the DJ named Mickey.
Haystak collaborated with Nashville, Tennessee native Jelly Roll on the album Strictly Business in 2011 which peaked at 67 on the Billboard 200 Top R&B/Hip-Hop Albums Chart, and 16 on the Top Heatseekers Albums Chart. The sequel Business as Usual was released on 11/19/13.
Haystak was originally from Lebanon, Tennessee. He claims Nashville because Lebanon is outside Nashville. Haystak's latest song is "Where I've Been", based on his life and what he has learned.