1. Lil’ Kim’s Purple Pasty
For most starlets and singers, having one of your breasts pop out on the red carpet would be an absolute nightmare. For Lil’ Kim, it was intentional. Back before she began going under the knife to alter her face and body, Kim was all smiles at the 1999 VMAs in a one-shouldered body suit that covered only one of her breasts. She stuck a matching pasty over the other and called it good. Her bright purple wig added some more zaniness to her appearance.
When presenting an award, Diana Ross was stunned at Kim’s outfit and even touched the bare breast. Unsurprisingly, years and years later in 2013, Miley Cyrus copped the rapper’s look and did a recreation for Halloween. Lil’ Kim was never afraid to wear whatever she wanted, and she proved it on this night in 1999. This purple outfit will forever live on, since it’s almost always mentioned whenever someone talks about VMAs past.
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