Most Iconic VMA Moments: Lil’ Kim’s Left Breast Steals the Show in 1999

Welcome back to Celebuzz’s Most Iconic VMA Moments showdown. In anticipation of of the 2013 MTV VMA ceremony on August 25, we want you to help us name the most iconic VMA fashion moment ever. Last week, we asked you to vote for your favorite VMA performance. (Britney Spears’ 2001 performance of “I’m a Slave 4 U” won in that category.) This week, it’s all about the clothing (or lack thereof). Return each day this week for a new feature on each of our competing fashion statements. You may vote once per hour.

Is Lil’ Kim’s “purple pasty” outfit the most iconic VMA fashion moment ever? Vote below, and read on for an in-depth look back at the rapper’s memorable appearance at the 1999 VMAs.

Lil’ Kim’s Purple Pasty: A Look Back at the Shocking Ensemble

Before anyone had heard the name Nicki Minaj, there was Lil’ Kim. A protege of The Notorious B.I.G., Kim achieved great success in the mid-to-late ’90s as a rapper and controversial figure. In 1999, more than three years after her debut album, Hard Core, dropped, Kim was gearing up to release her sophomore effort, The Notorious K.I.M. She showed up on the 1999 VMAs red carpet wearing what is undoubtedly one of the most memorable ensembles of all time. Notorious, indeed.

The outfit, designed by Kim’s stylist, Misa Hylton-Brim, is now almost 15-years-old, and we still haven’t forgotten it. At the time, Kim was well-known in the hip hop world for her sexually-charged raps and outrageous fashion choices. Dressing in head-to-toe purple would have turned heads regardless, but the fact that her left breast hung out, covered only by a sequined pasty in the shape of a shell, made Kim’s look the most talked-about thing of the evening. Or, to quote the lil’ woman herself:  “T*tty out like WHA / I don’t give a F@#%!”

Of course, for all of the red carpet “OH MY GOD”s and “WTF”s caused by Kim’s outfit, the real shocker didn’t come until showtime. When Kim took the stage with Mary J. Blige and Diana Ross to present the award for Best Hip Hop Video, Diana reached over and jiggled Kim’s breast in front of the entire audience. Ladies and gentlemen, when music royalty feels you up on national television, you know you’ve made a truly outrageous — and iconic — fashion impression.

Don’t forget to cast your vote for the most iconic VMA outfit above. Again, you may vote once per hour. Return each day this week for a new feature on each of the outfits in our poll.