After over a decade of playing in various punk rock and hardcore bands, in 2004 Riley returned to his roots and began playing country and folk music in the bars and cafes of St. Louis, Chicago, Kansas City and every little Midwestern town in between. In 2006, Riley self-released his debut album Whiskey, Ramblin, and St. Louis Nights (James Whitlock, Homeset Studios), which contains songs of sorrow and redemption.