Recorded in June of 1981, Heartbreak was produced by two enthusiastic fans, brothers Rick and John Chelew. They enlisted musicians like Albert Lee and Jennifer Warnes to accompany Bert in the small Silverlake Studio where the album was recorded.

During the sessions for the album, Bert also played a few live gigs at the legendary folk club, McCabe's Guitar Shop in Santa Monica, California. Now the 30th Anniversary edition of Heartbreak has been further enhanced by a previously unreleased, complete live show from McCabe's Guitar Shop.