Early in his career, he was in the San Francisco art band Eye Protection, which had one track on the compilation Rising Stars of San Francisco: "Take Her Where The Boys Are". They also recorded a 7-inch single called "Elroy Jetson" with a b-side of "Go Go Girl" on Eleph Records.
Later, he replaced Stan Ridgway as the lead singer of Wall of Voodoo when Ridgway left the band in 1983. Seven Days in Sammystown was the first Wall of Voodoo album featuring Prieboy. This was followed up by Happy Planet and finally Ugly Americans in Australia, which was a live album they recorded to fulfill their recording obligations to IRS Records.
In the mid-to-late '90s Prieboy played shows at the Los Angeles hipster club Largo with Rita D'Albert where they worked on an ongoing musical, White Trash Wins Lotto; a Gilbert and Sullivan-esque treatment of the rise and fall of an Axl Rose-like character. It was also performed at the Roxy Theatre on the Sunset Strip for three sold out weekend-long engagements as well as two sold out weekends at New York City's PS 122. Prieboy and crew also performed a medley from White Trash on the Conan O'Brien show.
Prieboy is also the co-author with Merrill Markoe of the novel The Psycho Ex Game, based on his song "Psycho Ex". Markoe and Prieboy have lived together since 2004.