Rob Crosby was born and raised in Sumter, South Carolina, graduating in the Sumter High School class of 1972. 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. During High School and college, he performed in South Carolina, and eventually across the Southeast. In 1984, Crosby moved to Nashville with his family and began playing in local clubs.

In 1984, an Atlanta businessman offered Crosby $700 a month for a cut in his Future songwriting royalties. After getting a job as a staff Writer, country music group Chance took his song "She Told Me Yes" to the top 30 in 1985. Since then, many songs written by Crosby have reached the Billboard top 10, including "Friday Night" by Eric Paslay, "Concrete Angel" by Martina McBride, "She's More" by Andy Griggs and "Holdin' a Good Hand" by Lee Greenwood. Crosby's songs have been recorded by Blackhawk, Brooks & Dunn, Ty Herndon, Paul Overstreet, Carl Perkins, Restless Heart, Ricochet, Paul Simon, The Wilkinsons and Darryl Worley, among others.

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. 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.