To celebrate the incredibly prolific, influential and diverse body of work left behind by Prince, we will be exploring a different song of his each day for an entire year with the series 365 Prince Songs in a Year.

By 1987, Prince was already an established megastar, one of the world's biggest. So he could pretty much do whatever he wanted. And when it came time to pick the second single from his double-LP masterwork Sign o' the Times, he exercised that right by choosing one of the album's weirdest tracks as his next potential hit.

The album's March 30, 1987, release was preceded six weeks earlier by the title track, an oddball choice for a single itself, a stripped-down solo song mostly played on a synthesizer, and some backing vocals, about AIDS, the Space Shuttle disaster, drug abuse and gang violence. It climbed its way to No. 3, despite being Prince's most airwaves-unfriendly single since 1999 took him to another level five years earlier.

On May 6, a little more than a month after Sign o' the Times came out and started to work its way up the chart to a No. 6 peak, "If I Was Your Girlfriend" was pulled as the next single from the album. It became Prince's lowest-charting single since a series of Controversy tracks struggled to gain momentum in the pre-1999 days, stopping way short of the Top 40 at No. 67.

It deserved much better.

Like most of the songs from Sign o' the Times, "If I Was Your Girlfriend" began life for another Prince project. Originally pegged to both the unreleased Crystal Ball album and Camille, an LP credited to a Prince female alter ego named Camille, the song bears all the hallmarks of the latter record. Most notably, his vocals were sped up to the point where he sounded like a helium-dosed robot. More subtly, Prince sang Camille's songs from a point of view of an androgynous, and often horned-up, lover.

Three of the tracks from the abandoned project, including "If I Was Your Girlfriend," ended up on Sign o' the Times. One found its way on the delayed Black Album, another on a soundtrack and two were B-sides, one of which, "Shockadelica," was the flip of "Girlfriend." Much to the song's credit, it fits squarely into each of the albums it was tied to during 1986-87.

Nestled in the middle of Sign o' the Times' Side 3, arguably its best side, "If I Was Your Girlfriend" strikes a sexily cool position after "U Got the Look," recalling Prince's earlier stripped-down solo work, when it was often just him and his synth in the studio. "If I Was Your Girlfriend" is entirely solo, just bass, drum machine and a spare keyboard. (Its slinky riff eased it into a too-faithful cover on TLC's hit 1994 album CrazySexyCool, which is a pretty apt description of Prince's original version.)

Lyrically, it's on another plane altogether, as Prince runs down all the things he could do for his woman if they weren't sexually involved. It starts innocently enough. "If I was your girlfriend, would you remember to tell me all the things you forgot when I was your man?" he asks. But by the end of he song, he gets into more Princely territory: "Would you let me see you naked then? Would you let me give you a bath? Would you let me tickle you so hard you'd laugh and laugh? And would you let me kiss you there? You know, down there where it counts?"

It's a brilliant move pulled off with both style and sex (indeed, "If I Was Your Girlfriend" is Sign o' the Times' most sensuous song). And in a charming new twist, Prince sounds surprisingly vulnerable in this rare role of gender reversal that's played for understanding relationships, as opposed to his past flirtations with this sorta thing, when these positions were adapted purely for sexual reasons.

Is it any wonder the song wasn't a hit with Top 40 listeners?

It was way too sophisticated, smart and subtle — not to mention defiantly weird — for airplay at the time. It still sounds like something from another time and galaxy all these years later. But "If I Was Your Girlfriend" is also universally timeless, which goes a long way in explaining its appeal. In a way, the song represents Prince's mid '80s state of mind, post Purple Rain: anything goes, no matter how deliriously off the wall.

Prince Albums Ranked in Order of Awesomeness

More From Mix 97.9 FM