During the early '80s, popular Kentucky band Radio Café made a name for themselves playing weekends in clubs and at events in the Midwest and Southeast. When the time came to make a decision to pursue music full-time, only singer/songwriter Kiya Heartwood and drummer Kopana Terry made the commitment to go for the brass ring. The pair changed the name of the band to Stealin' Horses, for a Native American tribal ritual, and soon thereafter relocated to Nashville, signing a production deal with Castle Studios. The studio arranged a number of regional showcases for interested labels while Heartwood and Terry recorded the songs that would become their debut album, scoring a deal with Arista Records. The recorded tracks didn't meet the label's expectations, however, and the band traveled to Los Angeles to work with producer Greg Ladanyi and a handful of studio musicians, including guitarist Waddy Wachtel and keyboardist Jai Winding. During the sessions, Neil Young dropped by to add harmonica to a few songs, and the band's self-titled debut was released to critical acclaim in 1988.
Recruiting former Roman Holiday guitarist Brian Bonham and bassist Jon Dumo, Stealin' Horses hit the road for the better part of two years in support of their debut album, touring with acts like the Del Lords, the Smithereens, and the Lemon Drops. When Arista dropped the band in 1990, Bonham and Dumo left as well; the British musicians were never comfortable with Heartwood's folk-rock leanings. Heartwood and Terry asked Kentucky friend Kelly Richey to fill in on guitar and the trio toured the Southeast for a year while working on new songs. Richey left the band to pursue a solo career, and Heartwood and Terry relocated to Oklahoma, hooking up with guitarist Kevin Clark, bassist Steve Kirkpatrick, and multi-instrumentalist Tim Gilliam to record their second album, Mesas and Mandolins, in 1991. Stealin' Horses broke up for good a year later; Heartwood recording a solo country album, True Frontiers, in 1993. Heartwood joined with Miriam Davidson to form the folk duo Wishing Chair in 1995. Former Stealin' Horses bandmate Kopana Terry joined Wishing Chair in 2001.