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The Five Most Embarrassing Moments in VMA History

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Wed, Aug 24, 2011 at 6:00 AM

click to enlarge Honorable Mention: RuPaul and Milton Berle throw down in 1993
  • Honorable Mention: RuPaul and Milton Berle throw down in 1993
The VMAs will air this Sunday night live from the Nokia Theatre, right here in L.A. Sadly, we won't be able to see Milton Berle grab at RuPaul's hooters, and we won't be able to hear her retort: "So you used to wear gowns, and now you're wearing diapers." Here's hoping, nonetheless, for something as embarrassing as the following.

5. Madonna kisses Britney

2003

Though something like this might have been big news in the '80s, or even the early '90s (remember Madonna's Sex book? Pretty tame by Kardashian standards), these two pop tarts were going for shock on the cheap, which left everyone rolling their collective eyeballs.

4. Master P performing "Make Em Say Uhh!"

1998

With what seemed like half of New Orleans on stage with him, P performed a headache inducing version of his signature tune. Somehow his live version of this track -- not always easy to hear in the first place -- was worse.

3. Michael Jackson kisses Lisa Marie Presley

1994

When the daughter of The King and The King of Pop married, many people were left scratching their heads, or speculating that it was all for show. Their kiss at the 1994 awards seemed to be an attempt to show -- in the days before Al locked lips with Tipper -- that there was substance to their nuptials. But let's just call it what it was: a fail.

2. The new Guns N' Roses

2002

When host Jimmy Fallon announced a surprise guest at the 2002 VMAs, the room buzzed with anticipation. When it was revealed to be GnR, the place went batshit crazy. Nobody expected, however, to see the fat Elvis version of Axl Rose, sporting a bootleg Oakland Raiders Jerry Rice jersey, sweatpants and incredibly awful braids. Then, there was Buckethead on guitar. Watch for the disappointed (or perhaps horrified) looks on audience members' faces.

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