Believe it or not, there was a time when MTV's Video Music Awards were not as pointless as they are now. The award show had the power to defy reality. It was where aging superstars could French kiss former Mouseketeers and a Chicago rapper could interrupt the acceptance speech of America's sweetheart. The network had the power to make or break a star, and their flagship award show was where stars were born. So when a 25-year-old rapper from Brooklyn wore a lavender jumpsuit with her entire left breast exposed, she didn't just turn heads—she made the world remember her name. The look, styled by Misa Hylton, propelled the Hard Core rapper into global stardom, where she spent the rest of her career pushing the limits of how sexy a woman could be in hip-hop.
Lil' Kim, fresh off the heels of the striking visuals of "Crush on You," didn't just sit in the audience partially nude, though. A bewildered Diana Ross patted Kim's pasty-encrusted breast on the main stage before announcing the nominees of the show's first-ever Best Hip-Hop Video award. That gesture almost eclipsed the outfit's sheer outlandishness, landing both outfit and boob tap firmly into never-to-be-forgotten status.
There would have been no iconic boob tap moment without Hylton. The celebrity stylist is responsible for the looks of legendary artists like Mary J. Blige, Missy Elliott, and of course, the First Lady of Junior M.A.F.I.A. "Crush on You," a video also styled by Hylton, was Kim's introduction to MTV's audience, making her more than a regional rap star. "She became the sweetheart of rap even though her persona is so hardcore," Hylton said in a 2017 interview with Hot 97. While the collaboration with Lil' Cease predates the boob tap by two years, the purple pasty was inspired both by the creative direction for "Crush on You" and an unconventional idea from Missy Elliott.
"We were hanging out kicking it and talking about fashion and music and [Missy] told me, 'If I was Kim I would always just have one titty out and be like, fuck it,'" Hylton told The Fader in 2016. Hylton saved the idea for Kim's next big moment: the 1999 Video Music Awards.
"We had just came off the 'Crush on You' video where she did the primary colors," she said on The Premium Pete Show. "So I was like, 'Let's go the pastel route. This time let's do something softer. If you're going to be half-naked, let's soften it up a bit." It wasn't until the next morning, after wrapping the "Quiet Storm Remix" video, that Hylton realized how much controversy the outfit sparked. "I had no idea it was going to be such a hit," she told MadameNoire. "We just thought it was fly," Hylton told Hot 97.
Last month at Essence Fest, Lil' Kim reflected on the outfit, which she considers to be her most iconic moment. "It was like, 'All right, I got away with this one,'" she says. "Getting away" with an exposed breast (well before Janet Jackson's Nipplegate) meant the following year she could arrive on the VMA's red carpet in a red, caged corset with both breasts barely covered, and she did. The marriage of her lyrics and looks tested the limits of gender roles in hip-hop. In 2003, 50 Cent appeared shirtless on the cover of Get Rich or Die Trying. A month later, Kim released La Bella Mafia, where she was also shirtless. The Brooklyn rapper could do anything the guys could do.
When it comes to landmark moments like the boob tap, people assume they remember every minute detail of the jaw-dropping incident. With two decades behind us, we've realized there's actually a lot we forgot about the few minutes that Lil' Kim and Diana Ross shared a stage together.
For starters, Mary J. Blige was there. Blige is who introduces Ross as the "original diva of R&B," but her presence is overlooked once Ross joins the queens of hip-hop and R&B to announce the nominees for Best Hip-Hop Video. The former Supremes singer hits the stage to "I'm Coming Out," naturally, embracing the women as if she's known them forever. It was the original passing the torch moment; sorry, Britney, Christina, and Madonna.
Blige gets the kiss on the cheek your favorite auntie might give you, but Ross does what could be considered the first double-tap, 11 years before Instagram. The 55-year-old icon lifts Kim's unsleeved arm, gently jiggling the purple pasty—which was adhered by eyelash and weave glue (ouch!). It was the titty tap felt around the world. At that moment, no one cared who won the inaugural award for Best Hip-Hop Video. Blige seems to be the only one visibly disturbed that the Beastie Boys beat out Busta Rhymes' "What It's Gonna Be?," Lauryn Hill's "Doo Wop," and TLC's "Scrubs." There was no doubt about it: Lil' Kim won the night.
In the 20 years since the boob tap, many have tried to emulate the Queen Bee's look. Miley Cyrus got pasty-happy for Halloween in 2013 and Kylie Jenner wore a see-through lavender ensemble (sans exposed boob) and a matching purple wig to last year's Met Gala. Both looks, however, make us appreciate the original more. After all, you can't compete where you don't compare. There is only one Lil' Kim.
Kristin Corry is a staff writer for VICE.