Bob Woodruff played in rock & roll bands as a kid growing up in New York City and New York state, but when he started writing songs, country music was where he found his vehicle for expression. While attending college in New York, Woodruff started writing country-oriented songs and formed a band called the Fields, which developed a loyal following regionally and was offered a recording contract with Restless Records. The Fields recorded a low-budget record, but Restless went bankrupt before the album could be released, so at that point Woodruff decided to pursue music as a solo act.
He started playing gigs by himself and as his songwriting became more country, his lawyer was sending tapes to Nashville. In the meantime, Restless solved its bankruptcy problems and offered Woodruff another deal, but he ended up signing with Asylum Records' Nashville division in late 1992. His debut album, Dreams & Saturday Nights, was released in 1994 to critical acclaim, but his melding of R&B, country, and rock didn't go over at country radio and Woodruff ended up parting ways with the label after one album. Woodruff found a new home for his music at Imprint Records and released his second album, Desire Road, in 1997.