Prieboy's string of bad luck took a turn at a party in Los Angeles where a met an extremely drunk Bruce Moreland -- bass player for Wall of Voodoo -- who asked him to join the band as the replacement for recently departed lead singer Stan Ridgway. In 1985 the group -- with Prieboy -- released the critically acclaimed Seven Days in Sammystown, followed by 1987's Happy Planet and a live recording called Ugly Americans in Australia in 1988. That same year, after the band's demise, Prieboy wrote a song called "Tomorrow Wendy" for Concrete Blonde's breakthrough record, Bloodletting, and began work on what would become his debut, Upon My Wicked Son. Released in 1990 on the Doctor Dream label, the record combined Prieboy's fascination with vaudeville, art, opera, and satire, and was generally well received but did little damage commercially -- although "Loving the Highway Man" was covered by Linda Ronstadt and Emmylou Harris in 1999.
An EP followed in 1991 called Montezuma Was a Man of Faith, which featured a country version of Led Zeppelin's "Whole Lotta Love" sung with Concrete Blonde's Johnette Napolitano. In 1995 Prieboy's most ambitious project was released: the sprawling Sins of Our Fathers, which took on the record industry, psychotic ex-lovers, and religion with a wit and precision that established Prieboy as a true underground hero. Not long after, Prieboy debuted White Trash Wins Lotto, a play loosely based on the life of Guns N' Roses lead singer Axl Rose, ~ James Christopher Monger, Rovi