When Haystak broke into the Southern rap scene in the late ’90s, he set himself apart with a mix of larger-than-life charisma and self-reflective sincerity. Unlike many of his peers, he rejected materialism, instead rapping about life as “white trash” and the struggles of being underprivileged in the South. Born Jason Winfree in Lebanon, Tennessee, he was raised by his grandparents after his teenage parents split, growing up in poverty and turning to crime in his youth. After serving time for drug possession at 15, he found an outlet in rap, though few expected success for a white country boy in hip-hop. Defying the odds, he linked with local label Street Flavor Records and producers Kevin Grisham and Sonny Paradise, leading to his 1998 debut Mak Million and 2000’s Car Fulla White Boys, which earned him underground acclaim. His growing regional buzz led Koch Records to re-release Car Fulla White Boys in 2000, followed by The Natural in 2002. Over the years, Haystak’s music gained traction, with albums like Came a Long Way (2009), Hard 2 Love (2010), and Strictly Business (2012) breaking into the Billboard R&B/Hip-Hop charts. His 2013 follow-up Business as Usual hit number 11 on the Heatseekers chart, and by 2016, his signature grit evolved into a more reflective style on his 22nd album, Still Standing, embracing the storytelling depth of legends like Scarface and late-era Tupac.