Released in 1990 as the lead single from his first solo album ...Upon My Wicked Son, Prieboy recorded the song as a duet with Johnette Napolitano.

"Tomorrow Wendy" was inspired by the suicide of a woman who Prieboy had known from a young age when they were both growing up in East Chicago, Indiana.

Wendy later turned to prostitution and drugs, and when she was diagnosed with HIV, she decided to commit suicide by taking a heroin overdose rather than go on to die of an AIDS-related disease.

"[4] The deaths of Prieboy's two grandfathers from cancer was part of the inspiration behind Wendy's questioning of faith in the song, "I watched them go through a long period of rage and anger and atheism, railing at the God they'd worshiped all their life.

He felt the song needed a woman's voice in addition to his own and contacted Napolitano, who agreed to provide vocals on the track.

"[10] On its release, Andrew Mueller of Melody Maker described "Tomorrow Wendy" as an "uncharacteristically restrained lament for a wearied prostitute as she contemplates death".

"[11] In 1990, American alternative rock band Concrete Blonde released their own version of the song on their third studio album Bloodletting.

It was released the following year as the fourth and final single from the album, and reached number 66 on Canada's RPM 100 chart in February 1991.

[20] Through Bloodletting, Concrete Blonde's version of the song preceded the release of Prieboy's recording by a couple of months.

[21] In a retrospective review, Ned Raggett of AllMusic noted that Concrete Blonde's version sees Napolitano "deliver [a] bravura performance of the bitter, heartbreaking lyric".

"[6] A live version by Concrete Blonde, recorded at the Malibu Nightclub in Long Island, was included on the US CD single release of their 1990 song "Caroline".