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Milli Vanilli wins, then loses
Upon the discovery that Milli Vanilli members Rob Pilatus and Fab Morvan didn’t actually sing on Girl You Know It’s True, the duo’s 1990 Best New Artist Grammy was rescinded, and the guys became the new faces of lip-syncing.
Bob Dylan gets soy bombed
Bob Dylan was duly befuddled during his performance of “Love Sick” at the 1998 Grammys when backup dancer Michael Portnoy went rogue, ripped off his shirt to reveal the words “Soy Bomb” on his chest, and convulsed in spastic dance moves for 30 seconds before getting yanked off stage.
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Eminem performs with Elton John
Eminem continues courting accusations of homophobia to this day, but at least he held hands with (openly gay) Elton John after they performed Em’s song “Stan” at the 2000 Grammys.
Jennifer Lopez wears that dress
No Grammy red carpet moment has ever been nearly as iconic as the green, barely-there Versace dress J.Lo wore to the 2000 Grammys (along with some double-sided tape).
In 2001, the Album of the Year nominees included Radiohead’s Kid A, Beck’s Midnite Vulture, and Eminem’s The Marshall Mathers LP… and yet it was Steely Dan’s Two Against Nature that took the prize?!
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Pink twirls above the Grammy audience
Pink is known for her athletic performances, but her acrobatics reached new heights at the 2010 Grammys when she flew above the audience on aerial silks and sang “Glitter in the Air.”
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Lady Gaga arrives from an egg
Way before A Star (was) Born, a strange bird named Lady Gaga was hatched… but only after incubating inside the egg for the length of the 2011 Grammys red carpet.
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Macklemore apologizes to Kendrick Lamar
After The Heist won the 2014 Grammy for Best Rap Album, Macklemore texted Kendrick Lamar to say, “You got robbed. I wanted you to win” — and then he posted a screenshot on Twitter, which even Drake thought was “wack as f—k.”
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Love is love
That same year, Macklemore joined Ryan Lewis and Mary Lambert to sing their hit “Same Love” — with an assist from Madonna — as Queen Latifah officiated the onstage weddings of 33 same-sex couples. Fetch the tissues!
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David Bowie finally gets his due
How is it that David Bowie — a prolific glam-rock star with 11 number-one albums — only won a Lifetime Achievement Grammy and a music video Grammy during his lifetime? The Academy at least gave his final album, Blackstar, four trophies at the 2016 Grammys, but the Thin White Duke died more than a year prior.
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Adele starts over
While performing “Fastlove” in memory of George Michael at the 2017 Grammys, Adele stopped singing and asked to take it from the top. “I’m sorry,” she said. “I can’t mess this up for him. I’m sorry. I can’t.”
The 61st Grammy Awards should be quite the spectacle, with Camila Cabello leading a star-studded opening number, Lady Gaga performing for the fifth year in a row, superstar Korean boyband BTS making their Grammys debut, and Katy Perry and Kacey Musgrave teaming up for a Dolly Parton tribute. But will we still be talking about the 2019 show years from now?
See the tough acts this year's Grammy ceremony has to follow in the gallery of unforgettable Grammy moments above.