In December 1996, Matthew Good Band signed a two-album deal with
Private Music. In mid-January, on the first day of pre-production for
Underdogs, the group was notified that BMG Entertainment North America was merging Private Music into
Windham Hill/
High Street Records, putting a halt to the production of the album. In mid-March, after negotiations, Windham Hill/High Street released the group from its contract. Good was paid what he was owed for the two albums, and the group decided to record the new album regardless of label support, using the money received from the divorce of their contract with Windham Hill/High Street to fund it. According to Good, the album cost $100,000 to produce. The group then agreed to release the album under a distribution agreement with
PolyGram Group Canada. ==Commercial performance==