In September 2001, Spears took the stage at the MTV VMAs with a boa constrictor and a dream: to be the hottest, most desirable pop star to ever leave the rainforest. Were it not for this moment, would we even have Katy Perry's "Roar" video?
What to wear: A green chiffon bra, teeny-tiny jewel-encrusted denim shorts, and flat, knee-high boots. Whatever you do, don't forget the snake (we recommend a stuffed one, but it's ultimately your decision).