Rapper Cowboy Troy burst onto the country music scene in 2004 with his unique "hick-hop" style, gaining attention with his debut album Loco Motive and hit single "I Play Chicken with the Train." His collaboration with Big & Rich on the track "Rollin' (The Ballad of Big & Rich)" helped establish him in the industry, marking the beginning of a successful career that continued into the 2010s.

Cowboy Troy's journey in country music began in 1993 when he met John Rich in Dallas. Inspired by a diverse range of artists from Jerry Reed to Run-D.M.C., Troy blended rap and country influences to carve out his own niche. After years of honing his craft and making waves with performances alongside Big & Rich, he secured a record deal with Warner Bros. Nashville and released several albums, including Black in the Saddle and King of Clubs, showcasing his versatility and enduring presence in the music industry.