On Sept. 5, 1991, music's biggest stars assembled for the MTV Video Music Awards. It was nearly three hours into the broadcast when Prince took the stage to deliver his latest single, "Gett Off." His performance would close the night’s festivities, though few could have expected just how big of a bang he’d deliver.

“This is the one. This is the reason I took the gig again,” host Arsenio Hall proclaimed to the audience inside the Universal Amphitheater in Los Angeles. “Prince and the New Power Generation!”

The performance was a sight to behold, with Caligula-like imagery borrowed from the track’s music video. The stage was engulfed with intertwining bodies, pillars of fire and dancers wearing next to nothing. At the center of it all was Prince, leading his sexually charged symphony while wearing a yellow lattice bodysuit. As he turned on stage, the audience got a glance of just how outrageous the performance was. There, in full view, was Prince’s butt, its cheeks protruding from two oval shaped holes.

The performance was all anyone talked about the next day. The Los Angeles Times called it an “all-out, simulated orgy,” adding that “Prince’s swingers’ scene was the kind of fleshy spectacle that sends writers running to their dictionaries to look up the proper plural for menage a trois.” Though many regard the scandalous performance as Prince’s defining VMA moment, it was far from his only connection to the annual award show.

Prince scored his first VMA nomination in 1985, only the second year of the event’s existence. The purple one was up for Best Choreography that year for his work on the video for “When Doves Cry.” He would lose to David Atkins, the choreographer behind Elton John’s “Sad Songs Say So Much.”

Prince avenged his loss the following year when he took home the first Moonman of his career for the choreography for "Raspberry Beret," a video which he also directed.

The 1987 ceremony delivered Prince’s first performance on the VMA stage. Shrouded in darkness and surrounded by smoke, the music icon began the set by wailing on his guitar. As purple lights revealed his figure, the rocker launched into an electrifying rendition of “Sign ‘O the Times.” After pausing briefly for applause at the song’s end, Prince rolled into an upbeat, joyous version of “Play in the Sunshine.” The singer even found time to introduce Sheila-E during his VMA set, joking that the drummer was “not bad for a girl.”

1988’s VMAs would prove to be Prince’s most prolific, at least in terms of number of wins. The singer took home two Moonmen for the video to “U Got the Look.” Though the clip earned Best Male Video and Best Stage Performance honors, it lost in the Best Choreography and Best Editing categories.

The next couple of years would be sprinkled with nominations in less popular categories. “I Wish U Heaven” lost ‘Best Special Effects’ in 1989, while “Batdance” lost Best Video from a Film in 1990.

In some ways, then, the 1991 performance served as a reminder to viewers, both in the live audience and watching at home. Though the Lovesexy album and Batman soundtrack had shown a more family-friendly side of the artist, Prince was still the coolest one in the room, always capable of jaw dropping theatrics.

He would appear again at the 1999 ceremony, after rebuffing the network’s offer to perform. “MTV originally asked me to perform a song. Of course I’m talking about ‘1999.’ I decided I’d rather come introduce my favorite group,” the icon quipped before bringing TLC to the stage.

After going more than a decade between nominations, Prince received his final VMA nod in 2004 when "Musicology" was among the contenders for Best Male Video. Though the purple one wouldn’t take home a Moonman that night -- the honor went to “Yeah” by Usher -- presenter Christina Aguilera noted that, “A lot of us wouldn’t be here without (Prince’s) brilliant and endlessly funky inspiration.”

Shockingly, MTV did not honor Prince at the 2016 VMAs, held several months after his death. The network was harshly criticized for ignoring both and fellow fallen icon David Bowie during the event that year. Also surprising, the network’s 'Video Vanguard Award,' which honors lifetime achievement, has never been given to Prince.

But at the 2019 VMAs, several stars, including Lizzo and Lil’ Nas X, paid tribute to Prince by wearing outfits inspired by the late singer’s unique style. Their homages further proved Prince's continuing influence on generations of artists.

Prince Magazine Ads Through the Years: 1978-2016