Folk music singer/songwriter Peter Bernas was born in Chicago, the son of Polish immigrants. Despite his family's financial struggles, he bought a guitar from a junkshop and taught himself how to play, inspired by hard rock and heavy metal bands like Metallica and Motley Crue. He became skilled enough to become a jazz guitarist in his high school band. He played in several local bands, but it wasn't until he and bandmate Ken Jagmin decided to change styles and enroll in a songwriting class at the Old Town School of Folk Music that anything came of his pursuits.
The class was taught by guitarist Ralph Covert, the former leader of the band the Bad Examples. Covert eventually produced debut albums for all three students in the class: Bernas, Jagmin, and Dean Goldstein, the leader of the band Coin. For the sessions for Bernas's album, Covert assembled a pickup studio band which included guitarist John Duich and bassist Pickles Piekarski, who both had also been in the Bad Examples. Duich died of a heart attack in January 1998, shortly after the sessions were completed. Other members of the studio band included drummer Ron Barnes of the band Middle 8, guitarist John Siegle of the Insiders, and keyboardist Buddha Slim of the Remainders, while Jagmin, Goldstein, and Jeff Vezain provided background vocals. The album of mostly original material, entitled May the Better Man Lose, was released by Waterdog Music in 1999.
In order to support the album, Bernas recruited bassist Ed Kurzeja to play with him. They soon formed the band Made To Be Broken with drummer Gregg Interdonato. Interdonato, who had been playing bass in Coin, collaborated on the music for the song "With You on My Mind" on the May the Better Man Lose album. The trio went to work on writing songs for an album.