After leaving Wall of Voodoo, Prieboy signed with MCA Music Publishing as a songwriter and went to work on new material for his first solo record ...Upon My Wicked Son, which featured the song "Tomorrow Wendy," about a woman dying of AIDS.
MTV initially rejected the song's lyrical content and tone but Prieboy and Mignone decided to feature the decaying cities of Hammond and Gary in Indiana as the "Wendy" character and the video received Buzz Bin status at MTV.
Linda Ronstadt and Emmylou Harris covered his song "Loving the Highway Man" from the same album.
In the mid- to late-'90s, Prieboy played shows at the Los Angeles 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.
In 2012 Prieboy released the four-song downloadable EP Every Lady Gets A Song, featuring accompaniment by former Dils bassist Tony Kinman and Devo drummer David Kendrick.
The album was left unfinished and abandoned in 1992; it was meant to be the follow-up to his first solo work, ...Upon My Wicked Son.