Rob Crosby was born and raised in Sumter, South Carolina. He wrote his first song when he was 9 years old, and by the time he started the fifth grade, he had his own band, The Radiations. In 1984, Crosby moved to Nashville with his family and began playing in local clubs.
After a performance at a songwriter's night, Crosby was signed to Arista Nashville. The label released his debut album, Solid Ground, in 1991. The first three singles, "Love Will Bring Her Around," "She's a Natural" and "Still Burnin' for You," all reached the top 20 on Billboard's Hot Country Songs chart. After the singles from Crosby's second album, Another Time and Place, failed to reach the top 40, he was dropped by Arista. In 1995, he signed with River North and released his third album, Starting Now. Both singles released from the project peaked outside of the top 60 on Billboard. The same year, he was offered a chance to join the country music band Burnin' Daylight (which featured former members of Southern Pacific and Exile); however, he decided to focus on his solo career instead.
Crosby returned in 2003 on CSC Records with One Light in the Dark, a collection of original songs. He has released two albums since, 2003's Time Is a Gypsy and 2007's Catfish Day.