Awards shows are finally getting back to the live events we know and love, allowing for lots of opportunities for jaw-dropping unscripted moments. After all, isn’t that why we watch these things in the first place? And after this year’s Oscar shocker, we may be in for even more outrageous surprises at the Grammys. From show-stopping performances to record breaking wins, we’ve gathered some of the most iconic Grammy moments of all time.
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Ella Fitzgerald won 14 Grammys over the course of her career, including a Lifetime Achievement Award. But in 1958, more than 20 years after her first performance at the Apollo Theater, the jazz legend became the first African American woman to win a Grammy.
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In 1984, pop superstar Michael Jackson set a record for winning the most Grammy Awards in one night. He took home eight gold statues, including Album of the Year for Thriller.
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Love was in the air at the 2014 Grammys. Queen Latifah married a mix of 33 same-sex and straight couples, while Macklemore and Mary Lambert performed their song Same Love. She even got her license to perform weddings in Los Angeles County in preparation for the event.
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Who could forget when Kanye West rushed the stage during Taylor Swift’s acceptance speech at the 2009 MTV Video Music Awards? He wanted to let everyone know that Beyonce deserved to win Video of the Year instead. In 2015 he sort of did it again, but this time it was a joke, When Beck won Album for the Year, Ye approached the stage appearing to interrupt the acceptance speech. But rather than causing trouble, West said he was just kidding and took his seat.
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At the 1998 Grammys, Aretha Franklin saved the show by delivering an epic performance. Luciano Pavarotti was supposed to perform, but he called in sick during the broadcast. Fortunately, Franklin was there to fill in. She performed her rendition of the classic aria, Nessun Dorma, and of course, stole the show.
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Well, this is awkward. In 1990, Milli Vanilli won the award for Best New Artist. The issue? Neither of them actually sang the song “Girl You Know It’s True,” which made them famous. Once the truth was revealed, their award was taken away.
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Nicki Minaj is known for her out there performances. But in 2012, she really ruffled some feathers. The rapper performed an exorcism on stage, complete with levitation, that ended up really angering the Catholic League who called her performance “vulgar.”
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In 1998, a member of the Wu-Tang Clan shocked the audience by making a huge statement. After the legendary hip-hop group lost the Song of the Year award to Shawn Colvin, Ol’ Dirty Bastard went on stage and grabbed the mic, saying he thought he was going to win. It was awkward, to say the least.
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In 1989, the Best Rap Performance category was added to the Grammy awards. And it was DJ Jazzy Jeff and the Fresh Prince’s ‘Parents Just Don’t Understand,’ that beat out the likes of LL Cool J and Salt ‘N Pepa, making the duo the first rappers ever to receive a Grammy Award.
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Mickey Guyton co-wrote her hit single “Black Like Me” in the wake of George Floyd’s death. And in 20201, the song earned her the honor of becoming the first Black female solo artist nominated in a country category at the Grammys.
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Hatian-Canadian producer Kaytranada made history at the 2021 Grammys. He became the first Black artist to win in the Best Dance/Electronic Album and Best Dance Recording categories.
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Megan Thee Stallion got the statue for Best New Artist at the 2021 ceremony, making her the first Black woman rapper to win in the category in 22 years. Lauryn Hill previously won the award in 1999.