Missy Elliott's “Supa-Dupa Fly” Is An Iconic Fashion Era

The stars aligned at The Beverly Hilton in Hollywood during BET Awards weekend for the 10th annual Culture Creator’s Leaders & Innovators awards celebrating the artists and performers that keep the pulse of creativity beating. The honorees included producing legend Jermaine Dupri, reigning king of satire and BET Awards host Druski, fashion trailblazer Bethann Hardison, media mogul Jason Lee, Abbott Elementary star Janelle James, former NFL star Andrew Hawkins, and music and style visionary Missy Elliott. Guests and Culture Creator awardees caught up with HelloBeautiful on the orange carpet of the ceremony and talked about all things Missy fashion ahead of her Amazon Music Visionary Icon Award speech. While there are many stand-out and unforgettable style moments in three decades of Missy slayage (think blown-up Black jumpsuits, Kangol hats, matching Adidas track suits, and bejeweled throwbacks) there is one inspiring visual that left a permanent stain on Hollywood’s collective creativity: the futuristic styling in the video for Missy’s debut solo-single, The Rain (Supa-Dupa Fly). Who can wear a garbage bag and make it look good?” Culture Creators’ honoree Jason Lee told HB. 

Missy revealed backstage at the MTV Music Video Awards in 2019 that to get the look (which was styled by June Ambrose) she had to walk to a gas station in Brooklyn decked-out in the patent-leather jumpsuit to be blown up by a tire pump. The envelope-pushing aesthetic choice in an age of scantily clad video vixens paid off. “The Rain” was nominated for Best Solo Rap Performance at The Grammys the following year, and the video remains a staple on Hollywood creative moodboards.Two-time Emmy nominated “Empire” makeup artist and Ashunta Sheriff Beauty CEO said that she was “shocked” (in a good way) when she first saw the styling for “The Rain” video. The curator of the Hip Hop Beauty exhibit said she was inspired by Missy’s makeup and avant-garde garments in her late 90s era. “She had on black lip liner with a red centerpiece, and then she had like this matte look with heavy contour. It was different. It was unique. She didn’t use her body. She just used something different: which was all creative-ness,” Sheriff said. Five-time Emmy award-winning documentarian Taj Paxton said that Missy’s pioneering look broke ground for how Black people saw themselves on screen. “She literally changed the way we watched music videos. Everything she did after that it felt like, ‘I have to watch Missy,’” she said. “That’s the definition of an innovator. There’s an art form before they come, and there’s an art form after they’ve arrived, and I definitely think she’s the defining line, singularly,” Paxton said. 

While accepting her award, Missy shared some humorous lore with the crowd of A-listers about the making of the game-changing hip-hop hit. “When I started this record, I was high off weed. And I started that record by saying, ‘When the rain hits my window.’ You know you gotta be smoking to start it like that,” she joked, before becoming overcome with emotion. “I be so full in my heart. You don’t know where I come from. And you don’t know my story. I’m a lot stronger on the outside, so when I see these things, they mean so much to me and my home,” she said, adding that visionary sight means world-building blind “years ahead” into the future with the understanding that the dots only connect in retrospect. “You look back and be like, ‘Dang, this makes so much sense now,’” Missy told the room.