33. Missy Elliot, Supa Dupa Fly
Supa Dupa Fly as an album cover was a stunt on the industry like no woman had ever done. No… the artistic direction wasn’t supa crazy. She didn’t overspend wild dumb on the budget to get it shot. But back in the late 90s, to have a plus-size woman to reclining back with her leg up with the posture of a boss, was simply unheard of. The colors were not feminine and soft. They were dark and powerful and she, the producer of a whole movement, set the tone for the next twenty years of a Hip-Hop heavyweight that transcended not only gender but also race.
At the time, she moved with a green fly on each sleeve of the album cover. Little did she know that in south-western nations in Native American culture flies are actually considered message-bearers or bringers of the first fire to humans … and with Supa Dupa Fly, Miss Misdemeanor brought the message that she was here to stay … and that with her presence she was bringing nothing but fire!