In 1989, Jacob's Trouble released their debut Terry Taylor-produced album, The Door Into Summer, a mixture of original numbers and cover versions of songs by The Beatles and The Monkees.
A year later the band released their second album, Knock, Breathe, Shine. The band received notice at the time for the song "About Sex", a song about the proper role of sex in society from a Christian perspective. Fearing a fundamentalist label, the band opted to remove the song from the album and replaced it with the more ambiguous "About Sex, Part 2". Despite this, the album was the group's best-selling record. They performed "About Sex" during a concert at Dellinger Park in Cartersville, GA.
After their second album the group added two new members (Ron Cochran on drums and guitarist Keith Johnston), allowing Davison to become the band's principal singer. The new line-up recorded the album ...let the Truth Run Wild!. After the album's release Blackburn left the band. The band went on to record one more record, the album Jacob's Trouble.
Jacob's Trouble split after their fourth album and its subsequent tour.