Born in Harrisburg, Pennsylvania, he was signed to the Chrysalis Records label in 1990 and released his debut album, Jeffrey Gaines, in 1992.

Gaines' acoustic version received some radio attention but neither side of the single managed to chart nationally in 1992.

Gaines has toured with artists including Tom Petty and the Heartbreakers, Tori Amos, Tracy Chapman, Melissa Etheridge, Sting, Bryan Adams, Heart, Gregg Allman, Richard Thompson, Joe Jackson and Stevie Nicks.

[8] In addition to the Gabriel song Gaines' sets of original material occasionally include covers of songs by other artists as diverse as Elvis Costello, The Monkees, and Roberta Flack, and he continues to perform live.

[9] In 2016, Gaines did an extensive career retrospective interview with The Pods & Sods Network.