Winfree was born to teenage parents in Lebanon, Tennessee, outside of Nashville. and was raised by grandparents. At the age of 15, he was arrested and convicted for bringing Valium and cocaine to school. He served two years and when he was released began a music career. He rapped about his life as so-called "white trash," exploring the social dimensions of being white and underprivileged in the South. In the late 1990s, he signed with a local rap label, Street Flavor, and began a business relationship with 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 began promoting his work. The attention attracted the label 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 is married and has two children. In addition to rap music, he has been featured on the documentary White Boyz Can't Rap and the film Hustle & Flow where he played the DJ named Mickey.
Haystak collaborated with fellow Nashville native JellyRoll 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 November 19, 2013.
Haystak was arrested on a charge of rape on February 17, 2006. Haystak was convicted of assault, fear of bodily injury after he pled guilty. He was given a suspended sentence of 11 months and 29 days and was instead sent to probation.