By 1996, Black's career was taking wings of its own. He appeared on recordings with Blackhawk, Sam Bush, and Iris Dement. In 1998, he joined up with drummer Ken Coomer, guitarist and keyboardist Jay Bennett, and bassist John Stirratt to record the album Birmingham Road, released on the Arista Records label. Long Way to Go, Ghosts in the Graveyard, Valley, and That's Just About Right are some of the tracks on this first album. Black returned in early 2003 with B-Sides and Confessions, Vol. 1. Featuring solo acoustic and sparse trio performances, it was a less rollicking record than Birmingham Road, but paid even closer attention to Black's sweet wine-and-rawhide vocals. Originally available exclusively through Black's website, B-Sides and Confessions was issued officially by Nashville indie Dualtone on March 18, 2003. In 2005 Black released Tin Lily, a warm, diverse and altogether more cohesive album of all new material, again on the Dualtone label. ~ Charlotte Dillon, Rovi