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Grammy Performance of the Weekend/Madonna/”Nothing Really Matters”

While there will always be much to tea to sip about any and every one of her performances because, well, it’s Madonna we’re spilling about here, this one is quite the exception as her Lady Geisha worthy performance of “Nothing Really Matters” not only opened the ’99 show, but it also led into Madge winning the trophy for Best Pop Vocal Album just a few minutes later for her still stunning Ray of Light record. 

But alas…the true slice of our Material Girl heaven that night came when Madonna–as well as the rest of the entire frickin’ world–got introduced to all of the likes of the fabulous Ricky Martin, who had destroyed our souls with his electrifying performance of “The Cup of Life” a little bit later in the evening. If you’ll recall (really, how can we forget?), Madonna became immediately obsessed with the “Livin’ La Vida Loca” singer during the telecast, which in turn was a clever disguise as an approval for all of us to do the same…and we most certainly did. 

While Martin was the real winner of the night, it was Madonna who the stole the show in the only way she knows how to do…by being Madonna and making it–and Ricky–her bitch. 

Cover photo courtesy of Today in Madonna History 

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