When "I Drove All Night" was written, Kelly and Steinberg wrote it in the style of Roy Orbison, but never expected Orbison to actually sing the song. However, in 1987 they convinced Orbison to record a demo at Kelly's house with Kelly on guitar or piano. Unfortunately, as Orbison didn't have any record contract at the time, Kelly and Steinberg didn't know what to do with the takes remained unused. Later, the demo sung by Tom Kelly was played for Lauper who then recorded it in 1988. Much later after Orbison's death, his demo was engineered by Jeff Lynne into a finished version.