David Gross started playing in the Chicago club scene and toured around the Midwest through the early '70s. He opened shows for a wide variety of musicians, including Odetta, Dave Van Ronk, John Prine, Tom Waits, The Flying Burrito Brothers, Sonny Terry and Brownie McGee, John Fahey, and even Supertramp. In the '80s, after a move to the West Coast, David was signed as a songwriter by Chappell music.