Cyndi Lauper — “When You Were Mine”: Prince’s Song, Sung Her Way

1983 · Behind the Songs

Before Prince was a global icon, he wrote a new-wave heartbreaker for his Dirty Mind album. Cyndi Lauper heard it, kept every word as written, and made it the emotional centerpiece of She’s So Unusual.

A polyphonic analog synthesizer keyboard
Photo: Klaus P. Rausch, Wikimedia Commons, CC0. Source · CC0 licence. Display resized; no retouching.

She’s So Unusual is remembered for its parade of hits — “Girls Just Want to Have Fun,” “Time After Time,” “She Bop,” “All Through the Night” — four singles that made it the first debut album by a female artist to generate four top-five Billboard Hot 100 hits. But the album’s beating heart might be a song that was never a hit at all. Tucked among the singles is “When You Were Mine,” a cover of a Prince song from three years earlier, sung by Lauper with a rawness that stops the party cold. It is the moment on the record where the colorful persona drops and a real person steps forward — and it may be the bravest vocal she ever committed to tape.

Prince wrote “When You Were Mine” for Dirty Mind, the 1980 album on which he fused funk, rock, and new wave into something entirely his own. Like nearly everything on that record, he played all the instruments himself, and the track’s signature sound came from an Oberheim OB-X synthesizer voiced to mimic a Farfisa organ — a wheezy, garage-rock keyboard tone that gave the song its nervous, jangly energy. Prince released it as a promotional twelve-inch single and later as the B-side of “Controversy” in 1981. It was never a chart hit for him, but musicians heard it. Rock singer Mitch Ryder cut a version in 1983 for his Never Kick a Sleeping Dog album, produced by John Mellencamp; it reached number 87 on the Hot 100 and turned up in the 1984 film Hot Dog…The Movie. The song was already developing a second life as other artists’ discovery when Lauper found it.

To understand what she did with it, remember where Lauper was in 1983. Her band Blue Angel had broken up in 1982 after one album for Polydor, and she had spent time waitressing and singing in New York restaurants and clubs just to pay the rent. She’s So Unusual, produced by Rick Chertoff and recorded from June to September 1983 at the Record Plant in New York, was her last shot — released October 14, 1983, on Portrait/Epic. She approached it like someone with nothing to lose, which may explain the fearlessness of “When You Were Mine.” A safer debut would have filled every slot with obvious singles. Lauper gave one to a Prince deep cut.

Singing it straight

Her version is a mid-tempo synthesizer arrangement that keeps the new-wave skeleton of Prince’s original but warms it considerably. Where Prince’s take is wiry and almost detached — a man cataloging his ex’s betrayals with a shrug — Lauper’s is openly wounded. And she made one decision that changes everything: she sang Prince’s lyric essentially as he wrote it, without flipping the perspective or softening the details. The song keeps its male pronouns, its specific images, its plainspoken account of loving someone who loved someone else. In Lauper’s mouth, the same words become a different story — not a complaint but a confession, delivered by a voice that cracks in exactly the right places.

It is worth considering how unusual that choice was in 1983. Female pop singers were routinely handed songs rewritten to fit a demure perspective; the industry assumed audiences wanted their heartbreak prettied up. Lauper, who had spent her pre-fame years singing in clubs where nobody cared about propriety, had no interest in prettied up. Her “When You Were Mine” is one of the great gender-blind vocal performances of the decade — proof that a lyric’s truth does not belong to the gender of whoever wrote it.

A vintage boombox radio cassette player
Photo: Smithsonian National Museum of African American History and Culture, Wikimedia Commons, CC0. Source · CC0 licence. Display resized; no retouching.

Release, reception, and the long tail

“When You Were Mine” was issued as a promotional single in the United States, and Lauper performed it on the 1985 American Music Awards — a striking choice for a televised showcase, and a sign of how much the song meant to her. It was not a commercial single in America, but it found an audience anyway: in Canada, it spent nine weeks on the RPM chart, peaking at number 62 in 1985, and a seven-inch single was released in Japan in 1985 backed with “Yeah Yeah” and “I’ll Kiss You.” For an album track that was never supposed to be a hit, it traveled remarkably far.

The album around it, of course, became a phenomenon. She’s So Unusual earned Lauper the Grammy for Best New Artist in 1985, with the album itself nominated for Album of the Year; it has since been certified sixteen-times platinum in the United States and sold some twenty-two million copies worldwide. In that context, “When You Were Mine” functions as the record’s conscience — the track that proves the pop machine had a human being inside it. Fans who wore out the singles eventually found their way to it, and many of them will tell you it is the song that made Lauper real to them.

Prince, for his part, was famously protective of his material and not always generous about other artists’ interpretations. But Lauper’s version has endured as one of the most respected Prince covers ever recorded — not because it outdoes the original, but because it understands it. She heard what the song was actually about beneath the Farfisa wheeze and the new-wave cool: simple, unglamorous heartbreak. And she sang it like someone who had lived it.

What to listen for

Play Prince’s 1980 original and Lauper’s 1983 version back to back. Notice the keyboard sound first — Prince’s Oberheim bark versus the warmer synth bed Chertoff builds for Lauper — and then notice how differently the same melody behaves. Prince rides it; Lauper leans into it, stretching certain phrases until they nearly break. Listen to the verses, where her voice drops to almost a murmur, and then the chorus, where it opens up without ever turning theatrical. The restraint is the point. And listen one more time to the lyric she refused to change — a small act of artistic integrity that turned a cover song into a statement.

Leave a Comment