4. Missy Elliott "The Rain (Supa Dupa Fly)" (1997)
Director: Hype Williams
The garbage bag suit, maybe the most iconic thing worn by anybody in any of these videos. See: Missy Elliott's music was surreal and quirky, full of lyrics that seemed almost plucked from the clouds rather than written out, as if she realized going in the complete opposite direction from Illmatic could pay even more creative dividends. And it was this weirdly loose lyrical approach that proved a perfect match for one of Hype Williams' most creative videos, the cartoonish cheekiness of "The Rain (Supa Dupa Fly)." With the aforementioned inflatable garbage bag suit, Missy became an unlikely style icon, transforming the jiggy era's shiny suits into even more exaggerated dimensions. The video is packed with cameos, from producer Timbaland to Puff Daddy, 702, Total, Yo Yo, Da Brat and Lil Cease, accompanied by dancers, multiple abstract set-pieces, shifting costumes and colors, all viewed through the rounded raindrop of Williams' fisheye lens, and Missy's ethereal music. This song wasn't born to be a single, but the video lifted it to the level of a hit.