Katy Perry
At the 2011 award show, the “Roar” singer wore a head-to-toe Christian Dior number that was topped with a yellow (cheese block–like?) cube hat. That year, the pink-haired Perry won Video of the Year for “Firework” as well as Best Collaboration and Best Visual Effects for “E.T.” featuring Kanye West.
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Macy Gray
To promote her 2001 album, Gray was a walking ad with the words “My new album drops Sept. 18, 2001” written in the front and “Buy It!” in the back. The year before, the singer won as Best New Artist for her single “I Try.”
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