2. Missy Elliott “The Rain (Supa Dupa Fly)”

Formerly Missy “Misdemeanor” Elliott and currently only Missy Elliott to the masses, her first video, Number 2, “The Rain (Supa Dupa Fly),” released in 1997, set a high standard for the rest of her video work.  Missy had been behind-the-scenes writing for other artists for years, when she finally introduced herself as a solo artist, with Supa Dupa Fly, she kicked the door down.  A few rap cameos along the way didn’t hurt. 

Sampling Ann Peebles’ 1973 hit, “I Can’t Stand the Rain,” this video featured Missy’s simple yet clever, nonsensical, and fun rhymes.  There’s unintelligent lyricism and then there’s this.  I think Missy’s style is sometimes mistaken for the former.  With a stripped down, melodic, and well thought out flow, she definitely has influenced other artists since.   With rhymes more bulky and complex at the time, she brought an alternative style that harkened back to old school roots with a ‘90s update.

I’ll name-check Hype Williams once more, because the collaboration between him and Missy is really what made this video special.  His fish eye lens effect, at this point, was fresh and not overwrought.  Name-checking other hip hop/R&B artists and actually having them in the video was a fun treat for music fans.  And the black trash bag outfit was bananas.  

Though her latest release, Block Party, has had many delays and single changes, refreshingly, not a skinny thing, at the time, Missy was, and remains, a true multi-threat performer with stage presence and charisma that’s carried her through with trash bag, flawless makeup and ‘dos, tomboyish yet feminine style, and talents for rapping, singing, dancing, and producing.