Painter grew up in Miami, and began playing trumpet, saxophone, bass, guitar and piano by age 11.
Painter met McWilliams while attending Belmont College in Nashville, and immediately began collaborating on songs. While pursuing a record contract, Painter began playing is studio sessions for artists like Indigo Girls, Nanci Griffith and Jewel (singer).
Fleming and John released their first album in 1995 for Universal Records.
Painter continues to work heavily in the Nashville area as a studio musician, performing on albums by Carolyn Arends, Ben Folds Five, Fear of Pop, Owsley, Rich Creamy Paint (Rich Painter, who is John Mark Painter's brother), Sixpence None the Richer and others.