With a crackling crystal ball, lightning effects and engulfed in a thick purple haze, Prince made his first-ever performance at MTV's Video Music Awards, which was held on Sept. 11, 1987 at the Universal Amphitheatre in Los Angeles.

It wasn't his first time at the ceremony, however. He'd won the award for Best Choreography in a Video the year before for "Raspberry Beret" and was nominated in the same category in 1985 for "When Doves Cry."

And although his videos from 1999 and Purple Rain had been in heavy rotation, he didn't make a personal appearance on the network until a 1985 interview, which was conducted by his manager Steve Fargnoli. For that segment he was surrounded by a crew who were on set filming his video for "America," and he discussed everything from his love of James Brown to his views on God and the afterlife, as well as the concept of Paisley Park as an "alternative."  At times, he appeared coy and other times, almost shy.

By contrast, his VMA slot was all power and energy. It was six months after the release of his stellar double album, Sign O' the Times, which dropped in March of that year and was his first release after the dissolution of the Revolution. Prince commanded the stage for nearly 10 minutes, performing both the title track from the album and "Play in the Sunshine."

Although he started out with his guitar wailing, he calmed down to deliver the somber message of "Sign O' the Times." By that time, the crack epidemic was in full swing, Reganomics was affecting disenfranchised communities and Prince—who remained in tune with social justice issues throughout his career—made sure to touch on those realities in the song.

"A sister killed her baby 'cause she couldn't afford to feed it / And yet we're sending people to the moon / In September, my cousin tried reefer for the very first time / Now he's doing horse, it's June." 

But a few minutes later, Prince shed his relatively melancholy vibe and turned energetic when he brought out Sheila E. who, clad in a red leather leotard, led a line of drummers at the foot of the stage so that they could rock out to "Play in the Sunshine." At one point, Prince shouted her out, saying, "Not bad... for a girl." 

You'd never know it watching the video (embedded above), but only his vocals and guitar were live. Everything else was pre-recorded.

Even though he performed, Prince wasn't up for any awards that night. And even if he had been, it would have been tough for him to beat Peter Gabriel, who won a record 10 Moonmen that year, with nine going for his classic "Sledgehammer" clip. But the following year Prince was nominated for four awards for his Sign O' the Times duet with Sheena Easton, "U Got the Look," of which he won for Best Male Video and Best Stage Performance in a Video.

He wasn't done at the VMAs, however. Prince would show up in 1991, with his sexually charged, assless pants rendition of "Get Off,"  which remains one of his most memorable televised performances, and one of the most notable VMA performances of all-time.

 

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