From Twerking to Biggie’s Mom-15 Most Badass VMA Moments

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12. Pasty Paradise

No one will ever forget the year Lil’ Kim dressed up as a purple mermaid for the VMAs in 1999. Of course, the most memorable aspect of her outfit was her left boob. Even in the late 90’s Lil’ Kim was audacious enough to go out in public sporting only a seashell pasty on her booby.

11. Boss’ Bounce

Diana Ross truly is The Boss, and when the disco queen came out onstage to join Mary J. Blige and Lil’ Kim in her boobylicious outfit, Ross just reached out and gave Kim’s lefty a baby jiggle, “hello.” Kim responded by whinnying like a small horse.

10. One Upper

Marilyn Manson’s ex-fiance Rose McGowan upped the ante when she appeared on the red carpet almost entirely nude in a see-through/backless negligee. At least she kind of matched weirdness levels with Manson.