The 10 Most Iconic Grammy Awards Moments of All Time

The Grammys are, without question, the most entertaining of all the awards shows. Musicians tend not to adhere to the same rules of etiquette that others in the business follow, and instead seem to operate under the assumption that ‘(s)he who gets the most attention, wins.’ The artists who appear at the Grammys are also often some of the most iconic public figures alive, which makes for compelling viewing no matter who wins the actual awards. Here, in anticipation of next week’s telecast, are some of the most iconic moments in Grammys history.

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Eminem & Elton John’s Duet

Back in very early aughts, Eminem received a lot of criticism from organizations like GLAAD for being homophobic, but it turned out that Elton John was a big fan of his at the time. The two performed Eminem’s song “Stan” onstage in a show of unity that Eminem hoped would help eliminate concerns about his relationship with the LGBTQ community. Watch the performance here.

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J-Lo’s Cleavage-Redefining Dress

It’s a little-known fact that the iconic Versace J-Lo wore to the 2000 Grammys was the catalyst for Google’s creation of its image search function. At the time, it was the most popular search query Google had ever seen, according to chairman Eric Schmidt, but the company didn’t feel there was a way to get users directly to photos of the dress. So, thanks to that plunging neckline, J-Lo changed the internet forever and made fashion history in one fell swoop.

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Lady Gaga’s Egg-cellent Arrival

In 2011, Gaga decided to ‘walk’ the Grammys carpet from inside a Hussein Chalayan-created egg as a nod to her song “Born this Way,” which she performed the same night. Watch the dramatic arrival here.

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Gwyneth Paltrow’s Duet with CeeLo

CeeLo inexplicably dressed up like a gay pride parade turkey for this performance of “Forget You,” but it was somehow still Gwyneth who garnered our attention. She climbed on top of CeeLo’s piano and gave the song her all in a show of spirit we are apt to forget exists within the oft reserved GOOP magnate. Watch the performance here.

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Bob Dylan’s Soy Bomb

Back in 1998, a performance artist named Michael Portnoy, who had the words ‘soy bomb’ scrawled across his bare chest, decided to stage crash Bob Dylan’s performance of “Love Sick.” He had originally been hired to nod his head in the background of Dylan’s performance (seriously!) and while charges were not pressed against him for the disruption, his payment for the gig was revoked. Watch the soy bomb here.

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Jennifer Hudson’s Tribute to Whitney Houston

Just one day after the legendary singer’s untimely death, Jennifer Hudson took to the stage to perform a heartbreaking rendition of Houston’s song “I Will Always Love You.” Watch her performance here.

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Milli Vanilli’s Revoked Grammy

After a lip sync fail at the 1990 MTV Awards revealed that the group’s Robert Pilatus and Fabrice Morvan were not actually singing any of Milli Vanilli’s songs, their Grammy for “Best New Artist” was revoked for the first and only time in Grammy history. Watch the MTV performance here.

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Michael Jackson’s 1988 Performance

In sharp contrast to the 1984 awards show in which Michael Jackson took home a record-breaking eight statuettes, he was defeated in every category for which he was nominated in 1988. Few save Jackson likely remembered the night for those upsets, however, as he gave an unforgettable performance that overshadowed just about every other element of the night’s programming. Watch his performance of "The Way You Make Me Feel/Man In The Mirror" here.

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M.I.A performs on Her Due Date

In doing so, she managed to somehow steal one of the most iconic moments in hip hop history from fellow performers Jay-Z, Kanye West, Lil Wayne, and T.I. Watch her anxiety (but not labor)-inducing performance here.


These days, it’s hard not to just type the word ‘Beyonce’ on repeat for every article we write about anything. She crushes it, always, so it’s fitting that not one but two of our most iconic Grammys moments come courtesy of the “Formation” singer. The first was in 2004, when she sang “Purple Rain,” “Baby I’m a Star,” and “Crazy In Love” with Prince. The second was in 2008, when she sang “Proud Mary” with Tina Turner, unwittingly stealing the crown from the iconic performer she called “the Queen.” Watch the Prince performance here and the Tina Turner performance here.