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Britney Spears and Madonna

In 2003, VMA MVPs Britney and Madonna teamed up (along with Christina Aguilera) for a startling performance that nabbed each of them additional spots on our list. The show opened with each of the younger stars paying tribute to Madonna's first-ever VMA appearance nineteen years earlier, singing "Like A Virgin" in not-so-virginal white. Then the Material Girl herself turned up in a suit to sing "Hollywood"…and to kiss Britney, then Christina, on the lips. (Missy Elliot popped out of a "wedding chapel" to rap the finale.) (CREDIT: Kevin Kane/WireImage)
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