The 2010 VMA Countdown: Diana Ross Gropes Lil’ Kim

The 2010 MTV Video Music Awards are only a few weeks away. The biggest party of the year features nominated clips by Lady Gaga, Eminem, Jay-Z, Ke$ha and Katy Perry and will feature performances by Kanye West, Justin Bieber, Drake, B.o.B and Florence and the Machine (with many more to be announced). In order to properly prepare yourself for what’s to come, every day the MTV Newsroom Blog will deliver a classic moment in the history of the MTV Video Music Awards. Today’s installment: Diana Ross has her way with Lil’ Kim.

The MTV Video Music Awards are a great forum for eye-popping, envelope-pushing fashion. Since the beginning, stars have been wearing the craziest, most extreme outfits their brains (and stylists) can dream up (and in Lady Gaga’s case, that happened four or five times at the 2009 show). At the 1999 show, Lil’ Kim set a new standard for VMA fashion.

In the middle of the show, three generations of divas took the stage in the form of Diana Ross, Mary J. Blige and Lil’ Kim. At the time, Kim was on top of the world, as her work on her solo debut Hard Core and on Puff Daddy’s album No Way Out made her the top female MC in the game. She always had an eye for fashion and a willingness to bare her skin, so it made sense that she came out wearing a sparkly purple one-piece jumpsuit with only a tiny stick-on piece over her otherwise exposed left breast. Her outfit was the hit of the show, especially after Ross reached out and played with the boob while the trio were on stage.

The 27th annual MTV Video Music Awards will be broadcast live from the Nokia Theatre in Los Angeles on September 12 at 9 p.m. ET.