Lil’ Kim and Diana Ross’ Epic 1999 MTV VMAs
Lil’ Kim and Diana Ross MEGA; Jim Smeal/BEI/Shutterstock

Three years before Janet Jackson’s Nipplegate controversy, Lil’ Kim actually left one breast exposed intentionally at the 1999 MTV Video Music Awards. The “Crush on You” rapper wore a jaw-dropping lavender jumpsuit that only covered half of her chest that night, with a shell-shaped pastie saving the outfit from being totally NSFW.

Even Lil’ Kim, however, couldn’t have expected co-presenter Diana Ross to get handsy on the stage of New York City’s Metropolitan Opera House. As the two women joined forces to present the Best Hip-Hop Video alongside Mary J. Blige, the R&B diva reached out and gave Kim’s exposed breast a little jiggle.

“I think it’s the new Supremes!” Ross quipped on stage of the trio.

On the red carpet earlier in the evening, Lil’ Kim told House of Style host Rebecca Romijn that she didn’t have qualms about the breast-baring jumpsuit. “I was like, ‘Yeah, I’ll wear that!’” she said.

The Girls Cruise star also credited longtime stylist Misa Hylton, who opened up about the jumpsuit in a 2018 interview with Dazed magazine. “I think that Kim and I were magical together and when you have that type of synergy only greatness can come forth,” Hylton said. “We were thinking outside of the box and unapologetically taking risks. People gravitate to that type of authentic and creative energy.”

For her part, Lil’ Kim reflected on her and Ross’ unforgettable moment in a 2013 interview with MTV. “I think it was more of like a friendly, ‘Oh, my God, you look sexy, girl, but do you know you have a boob hanging out?’” Kim said. “By the way, if I ever did a movie of my life I would get her to play my mom.”

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