RuPaul Butts Head with Milton Berle (1993)
Things got awkward onstage after Milton Berle sexually harassed RuPaul backstage. But the then-up-and-coming drag icon held her own against the comedian.
Drag Queens Pay Tribute to Madonna (1999)
Long before RuPaul declared "Night of 1,000 Madonnas," the VMAs paid tribute to the gay icon with some pre-RPDR drag talent.
Madonna, Britney, and X-tina Lock Lips (2003)
Nothing quite compares to the sapphic moment between these three gay icons. And nothing beats Justin Timberlake's reaction.
Lady Gaga Walks the Red Carpet with Gay Soldiers (2010)
It was two years before the repeal of DADT, and Lady Gaga made a red carpet statement, not only with her dress, but with her guests.
Lady Gaga Rock Jo Calderone Drag (2011)
Lady Gaga had just released the video for her powerful ballad, "You and I." That year, she showed up to the VMAs in drag as her male alter ego, Jo Calderone.
Frank Ocean Performs "Thinking' Bout You" (2012)
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caption="" photo_credit=""]Frank Ocean had recently come out, revealing his first relationship was with a man. That year, he made his awards show debut, performing "Thinkin' Bout You" at the VMAs.
Macklemore Wins for "Same Love" (2013)
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caption="" photo_credit=""]Macklemore, Ryan Lewis, and Mary Lambert melted our hearts that year with queer ballad, "Same Love." After performing the song at the VMAs with special guest, Jennifer Hudson, the music video won Best Video With a Social Message.
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