If I Was Your Girlfriend (3:46)

“If I Was Your Girlfriend” was the second single off Prince’s widely-acclaimed 1987 double album Sign o’ the Times. While it is today considered one of his most notable songs, at the time of its release, the song did not chart well in the U.S., perhaps due to the record’s androgynous vocal and gender-bending lyrics. The track was originally from the “Camille” project of 1986, which was to be released under the guise of an alter ego boy named Camille (see Prince’s poem in the Lovesexy tour program), rather than by Prince. Regardless, the song is actually sung from a male perspective to a woman, wherein Prince explores the possibilities of a more intimate relationship if he were his lover’s (platonic) girlfriend. Trouser Press names the song as one of the album’s highlights, noting that it “redefines a relationship in a surprisingly mature way”.[1] Musically, the song is based on a bass and drum machine pattern, punctuated by a keyboard line that evokes sadness. Prince’s sped-up vocals are intensely emotional and heartfelt.

According to engineer Susan Rogers, a rare technical error on her part led to distortion— albeit only on certain words. As recounted in Alex Hahn’s book “Possessed: The Rise and Fall of Prince,” Rogers thought Prince “was going to rip my head off” for the mistake. Yet, after hearing the playback, Prince loved the effect, which is featured on the released version.