Bob Woodruff

Growing up in New York City and other parts of New York state, Bob Woodruff performed with rock & roll groups during his youth, yet country music became the outlet he chose once he turned to songwriting. While enrolled in college in New York, he composed material with a country focus and assembled the Fields, a band that built a strong regional audience and landed a recording agreement with Restless Records. The Fields completed an economical album, but Restless declared bankruptcy before the project could reach stores, leading Woodruff to commit to a solo path instead.

He began booking performances on his own, and as his writing leaned further into country territory his lawyer forwarded demos to Nashville. Restless eventually resolved its financial troubles and extended a new offer, yet Woodruff chose to sign with Asylum Records’ Nashville division in late 1992. His first album, Dreams & Saturday Nights, appeared in 1994 to favorable reviews, but the blend of R&B, country, and rock failed to connect with country radio, and he parted ways with the label after that lone release. Woodruff subsequently joined Imprint Records and delivered his next project, Desire Road, in 1997.