It was 1983. Cyndi Lauper was basically a fireball of neon hair and thrifting-store chic, standing in a recording studio trying to figure out how to out-sing a ghost. That ghost was Prince. Most people don't realize that When You Were Mine Cyndi Lauper wasn't an original track written for her debut album, She's So Unusual. It was a cover. But calling it a "cover" feels kinda reductive, honestly. She didn't just sing it; she wrestled it into a New York street anthem.
Prince originally released the track on his 1980 album Dirty Mind. His version is sparse. It’s twitchy. It’s got that Minneapolis synth-funk skeleton that makes you feel like you’re in a basement club at 3:00 AM. When Cyndi got her hands on it, she slowed the tempo just a hair and turned up the emotional desperation. She made it bigger. She made it hurt more.
The Weird, Gender-Bending Lyrics of When You Were Mine
Here is the thing about this song: it is incredibly progressive for the early 80s. Or even for today. The lyrics tell a story of a narrator who is totally cool with their partner seeing someone else. In fact, the narrator even mentions letting this "other guy" sleep on the couch.
"I never was the kind to make a fuss / When he was there sleepin' between the two of us."
That’s a heavy line. When Prince sang it, it felt like a voyeuristic, experimental funk trip. When Cyndi Lauper sang it, she kept the "he" in the lyrics. She didn't change the gender to "she" to make it a more "traditional" heterosexual jealousy song. That was a massive deal. By keeping the original pronouns, she created this ambiguous, queer-coded, or just deeply open-minded narrative that most pop stars wouldn't touch with a ten-foot pole in 1983. It made the song feel dangerous. It felt real.
The production on the Lauper version is a masterclass in 80s layering. You’ve got those bright, jangling guitars that almost sound like The Cars or something out of the power-pop playbook. Then you have Cyndi's voice. She goes from a hiccuping whisper to a glass-shattering belt in the span of three seconds. It’s chaotic energy captured on tape.
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Why the She's So Unusual Version Hits Different
Rick Chertoff, the producer for She's So Unusual, knew they needed something to balance out the bubblegum pop of "Girls Just Want to Have Fun." They needed grit. They found it in the Purple One's catalog.
If you listen to the drums on When You Were Mine Cyndi Lauper, they’re dry. They aren't those massive, gated-reverb "In the Air Tonight" drums that defined the decade. They’re punchy and tight. This keeps the focus on her vocal performance, which is—frankly—insane. She captures the feeling of being a "doormat" in a relationship but singing about it with a weird sense of pride and heartbreak. It’s a contradiction.
Critics at the time, and even now, point to this track as the moment people realized Cyndi wasn't just a gimmick. She had taste. She wasn't just a "wacky" girl in tutus. She was a curator of great songwriting. Rolling Stone and Village Voice critics leaned into this track as the "serious" center of the album.
The Prince Connection and 1980s Synergy
Prince was notoriously protective of his music. However, he seemed to have a respect for Lauper's interpretation. While he didn't give many interviews about it, the fact that he allowed the cover to be a prominent part of her debut—which was destined to be a blockbuster—says a lot.
At the time, the Minneapolis sound was just starting to invade the mainstream. By Lauper covering Prince, she helped bridge the gap between the burgeoning "New Wave" scene in New York and the "Funk-Rock" revolution happening in the Midwest.
The Legacy of a Non-Single
Believe it or not, "When You Were Mine" wasn't even a major Top 40 single in the U.S. for Cyndi. "Girls Just Want to Have Fun," "Time After Time," "She Bop," and "All Through the Night" were the heavy hitters. But ask any hardcore Lauper fan, or any DJ who specializes in 80s alternative, and they’ll tell you this is the best track on the record.
It’s the "cool" song. It’s the one that didn't get burned out by overplay on Top 40 radio, even though it was played constantly on fledgling MTV. The music video—or rather the live performances of it—showcased her rawest energy. She would jump around, her voice cracking in just the right places, proving that she could out-rock the rock stars.
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How to Appreciate the Song Today
If you want to really "get" this song, you have to do a side-by-side.
- Listen to Prince’s Dirty Mind version first. Notice the thinness, the urgency, and the way he almost mumbles the scandalous lines.
- Immediately switch to Cyndi’s version. Feel the wall of sound hit you. Notice how she emphasizes the word "mine" with a sort of tragic possessiveness that Prince didn't quite lean into.
- Pay attention to the bridge. The way she wails "I love you more than I did when you were mine." It’s a paradox. How do you love someone more after they’re gone and after they’ve treated you like an afterthought?
That is the emotional core of the song. It’s about the obsession that grows in the absence of a person. It’s about the pathetic, beautiful reality of unrequited love.
Actionable Listening Guide
To truly understand the impact of When You Were Mine Cyndi Lauper, look for the live version from her 1984 appearance on Top of the Pops or her early tour footage. You can see the perspiration. You can see the way she uses her whole body to squeeze out those high notes.
For musicians, try playing the chords. It’s a simple progression—mostly I, IV, V stuff—but the rhythm is syncopated in a way that’s harder to nail than it sounds. It requires a "galloping" feel on the guitar that bridges the gap between punk and pop.
Next time you’re building a playlist that isn't just the "standard" hits, drop this in right after some Elvis Costello or The Pretenders. It fits perfectly in that "Smart Pop" niche that defined the early 80s before everything became too glossy and synthesized. Cyndi Lauper proved with this track that she was a powerhouse, a visionary, and someone who knew a great song when she heard one—even if it was originally written by a guy from Minnesota who liked to sleep on his partner's couch.
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To dig deeper into this era of music, analyze the tracklists of She's So Unusual and Prince's Dirty Mind back-to-back. Notice the shared DNA in the synth arrangements and the subversive lyrical themes. This isn't just 80s nostalgia; it's a blueprint for how to reinvent a song while respecting its creator's weirdest impulses.