5.
Annie Lennox
“Why”
Best Female Video
Long before people like Jinkx Monsoon and Vivienne Pinay put themselves on YouTube and showed everyone the laborious process of applying drag maquillage, we had this highly emotional (and Dangerous Liaisons-esque) video for “Why,” where Annie Lennox dolls herself up in vibrant makeup and an astounding headpiece before proclaiming the song’s self-empowering final lyrics to the camera. Annie Lennox’s expressions are both arch and sincere, and it’s just the most moving and gay.
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