9. The Day the Bubble-gum Burst (2000)
Performing The Rolling Stones' "I Can't Get No (Satisfaction)," pop tart Britney Spears went from nice to naughty in nine seconds flat. In one amazing move, she managed to peel off her clothes and strip herself of her innocent persona. Teenage boys and creepy old men everywhere rejoiced.
7. Oops! (2000)
In a classic MTV moment, host Shawn Wayans had the temerity to question Britney's big single, "Oops, I Did it Again," wondering out loud what, exactly, Ms. Spears had done the first time.
1. Britney and Madonna's Tongue Twister (2003)
Twenty years after her VMA debut, Madonna managed to make the infamous Michael Jackson/Lisa Marie Presley '94 VMA kiss seem bland by closing her "Like a Virgin" show opener with an opened mouth May-December smooch with Britney Spears.