By Wonderwall.com Editors
5:00pm PST, Feb 5, 2024
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The 66th Annual Grammy Awards air live from Los Angeles on Feb. 4, 2024. To mark the occasion, we're looking back at the wildest moments from the annual award show over the years, starting with this one from 2020…
Billie Eilish swept all the major categories at the 2020 Grammy Awards! The then-18-year-old singer was the youngest person to earn nominations in all four major categories in the same year — album, record and song of the year plus best new artist — and then she won them all (plus an award in the pre-telecast: best pop vocal album). She also became the youngest person ever to take home a song of the year Grammy (for "Bad Guy"). After winning album of the year — and making history as the youngest artist to ever receive that trophy (an honor previously held by Taylor Swift), Billie told the audience, "Can I just say that I think Ariana [Grande] deserves this?" Then, right after that, Billie won record of the year too!
Keep reading for more of the most buzzed-about moments from Grammys past…
MORE: Stars at their first Grammy Awards
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Beyonce set a massive record at the 2023 Grammy Awards when she picked up four more Grammys and officially became the most decorated artist of all time. (The superstar previously set a record in 2021 when she became the most decorated woman in Grammys history.) The singer took home the gramophones for best dance/electronic recording for "Break My Soul," best dance/electronic album for "Renaissance," best traditional R&B performance for "Plastic Off the Sofa" and best R&B song for "Cuff It" — which helped her reach an astounding 32 career wins, beating the previous record held by late classical musician Georg Solti, who won 31 Grammys over the course of his critically acclaimed career.
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Jennifer Lopez ushered in a new millennia of fashion at the 2000 Grammy Awards when she wore this sheer green Versace gown with a deeply plunging neckline. (Can we even call it a neckline when it hits below her navel?!) While we've seen far more outrageous gowns since, it was Jenny from the block who first dared to bare her killer bod in a dress that left little to the imagination. 2000 also marked the year non-celebrities learned about the magic that is body tape.
MORE: Most memorable Grammys fashion ever
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After being labeled homophobic by critics, Eminem shoved a metaphorical middle finger in everyone's face when he performed his hit song "Stan" alongside one of the greatest performers (and most well-known members of the LGBTQ+ community), Elton John, at the 2001 Grammy Awards. It was the rapper's team that reached out to Elton for the possible duet, which the British musician happily agreed to, marking the beginning of the two performers' long friendship.
MORE: Stars who've won the most Grammys
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In 1990, the German R&B group Milli Vanilli — consisting of members Rob Pilatus and Fab Morvan — won the Grammy for best new artist following the success of their hit sophomore album, "Girl You Know it's True." The only problem? Neither Rob nor Fab sang a single note of it. When the lip-syncing scandal broke, the Recording Academy did something it had never done in its history and rescinded their Grammy. The duo attended a press conference on Nov. 20, 1990, where they admitted Brad Howell and John Davis were the real singers on the album and deserved the award instead.
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Lady Gaga's egg-tastic arrival (and performance) in 2011 left many scratching their heads. Instead of walking down the red carpet, Gaga was carried — inside a giant egg — by a group of muscular male dancers. The singer was later wheeled onto the stage where she hatched from her egg to sing "Born This Way." After clarifying that the egg was actually not an egg but a temperature-controlled "vessel," Gaga shared that she stayed inside it for 72 hours. No word on if the vessel included a micro-bathroom and mini-fridge.
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At the 59th Annual Grammy Awards in 2017, British singer Adele won the coveted album of the year prize for "25." While that in itself is buzzworthy, it was Adele's speech that really sparked headlines. On stage, Adele said, "I can't possibly accept this award. I'm very humbled and I'm very grateful and gracious but my artist of my life is Beyonce and [her] album to me, the 'Lemonade' album, is just so monumental. Beyonce, it's so monumental. And so well-thought out, and so beautiful and soul-baring and we all got to see another side to you that you don't always let us see. And we appreciate that. And all us artists here, we f****** adore you. You are our light. And the way that you make me and my friends feel, the way you make my Black friends feel, is empowering. And you make them stand up for themselves. And I love you. I always have and I always will." Cue the tissues.
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Speaking of Beyonce, can we talk about her amazing gold dress at the 2017 Grammy Awards? Queen Bey wore the heavily embellished gown while pregnant with twins Sir and Rumi Carter during her performance of "Love Drought" and "Sandcastles" and had everyone in the audience (and at home) completely mesmerized. The glittering gown was designed by Peter Dundas, who said he incorporated rays of sunlight to pay homage to the African goddess Oshun and the beaded profile of Beyonce's face (on her tummy) was to "create a story in the garment."
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At the 58th Annual Grammy Awards in 2016, Kendrick Lamar reigned supreme after his jaw-dropping performance of "Blacker the Berry" and "Alright" while highlighting racial inequality and discrimination. The hip-hop star arrived on stage as part of a prison chain gang amid occupied jail cells and rapped about society's treatment of Black people. He also lamented the killing of Trayvon Martin, saying, "On Feb. 26 I lost my life too." The performance, which was intended to shine a light on the oppression and exploitation of Black people in the U.S., was hailed as both powerful and controversial by fans and critics alike.
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It was the hat that launched a thousand memes! Pharrell Williams was one of the big trending topics of the 2014 Grammys, but it wasn't because of his music. The artist-producer wore a striking larger-than-life brown hat by Vivienne Westwood to the award show, sparking instant commentary. It still lives in infamy!
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An amazing duet no one can forget is Joss Stone and Melissa Etheridge's 2005 Grammy Awards performance, which went down not long after Melissa finished chemotherapy and radiation treatment for breast cancer, which left her bald. The duo paid homage to singer Janis Joplin, who'd died 20 years earlier, by singing her hit songs "Cry Baby" and "Piece of My Heart." Literally everyone watching had chills when Melissa walked on stage that night. The singer claimed she didn't want to worry about a wig falling off, so she just decided to go without one — and made us all love her a whole lot more.
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Annie Lennox caused quite a stir at the 1984 Grammy Awards when she arrived in drag. The show's producer didn't recognize the Eurythmics singer in her menswear look and frantically searched for her backstage when it was time for her to emerge. Little did they know she was standing right there! Annie is pictured here in her ensemble next to Eurythmics partner Dave Stewart.
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Of course Lady Gaga would make it on our list multiple times. The singer, who's long been known for shocking fans and fashion critics with her creative style choices, did not disappoint at the 52nd Annual Grammy Awards in 2010 when she arrived in an orbit-inspired Giorgio Armani Privé gown. Her look — a dress featuring swirling embellished hoops, plus sky-high silver shoes, hair the color of the burning sun and a large metal star — made Gaga look like she was the center of her very own universe.
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Yup, Beyonce made it on our list again. In 2008, Bey stood beside another legendary performer, Tina Turner, to belt out an awe-inspiring rendition of Tina's hit song "Proud Mary." The moment was a symbolic passing of the torch and we were all about it. Four years earlier at the 46th Annual Grammy Awards, Beyonce had delivered another memorable duet with another iconic singer, Prince, when they performed "Purple Rain" together — and it was everything we could have hoped for and more.
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We still can't stop talking about the 2016 Grammys opening number — a performance by the cast of "Hamilton." The long sold-out Broadway musical about the life of founding father Alexander Hamilton (written by and starring Lin-Manuel Miranda, along with an amazingly talented cast) has been one of the most sought-after tickets of the 21st century, making the cast's Grammy-night performance even more electrifying. Host Stephen Colbert joked about the number, claiming he still wasn't sure he could get tickets to the night's performance.
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Proving women really can do it all, a very pregnant M.I.A. performed "Swagga Like Us" at the 2009 Grammys alongside Lil' Wayne, T.I., Kanye West and JAY-Z. Wearing an adorable sheer black mini with black-and-white polka-dot patches, the British hip-hop star rocked her voluptuous belly, later revealing that the performance was on her due date! She gave birth to a baby boy, Ikhyd Edgar Arular Bronfman, three days later.
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While it was totally awesome seeing Justin Timberlake on stage with iconic singer Al Green at the 2009 Grammy Awards, the reason they performed together was not so cool. Originally, Chris Brown and Rihanna were scheduled to perform together, but the night before the award ceremony, the couple got into a heated argument that ended with Chris assaulting Rihanna, leaving her battered and bruised. Chris was arrested and neither he nor RiRi attended the Grammys the following day. As for JT and Al, they, along with Keith Urban and Boyz II Men, sang "Let's Stay Together" — which was exactly what no one wanted for Chris and Rihanna following his arrest.
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Justin Timberlake was basically forced to issue a public mea culpa before he could attend the 2004 Grammys. A week prior, he and Janet Jackson were embroiled in one of the Super Bowl's biggest controversies when he pulled off part of her top at the end of their halftime performance, revealing her bare chest to 89 million viewers in what was later dubbed "Nipplegate." Justin, who was nominated for five Grammys that night, agreed to say he was sorry (Janet, however, did not attend the Grammys as a presenter because she refused to comply). When Justin was announced as the winner of the best male pop vocal performance award for his song "Cry Me a River," he took the stage and said, "Listen, I know it's been a rough week on everybody. What occurred was unintentional and completely regrettable, and I apologize if you guys were offended." That night, Justin also won an invisible award for the greatest forced non-apology in Grammys history.
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The 2018 Grammys definitely brought the drama! Lorde — who was the only woman nominated for album of the year — refused to walk the red carpet before the ceremony because she reportedly felt disrespected after all four male album of the year nominees were offered slots to perform their own music during the telecast while she was only asked to participate in the multi-artist Tom Petty tribute, Variety reported. Yikes! Lorde is pictured here with her brother, Angelo Yelich-O'Connor, during the ceremony.
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Can we have a moment of silence for this unfortunate Christian Dior look Alicia Keys tried to rock at the 2002 Grammy Awards? The sheer embroidered sari was oddly draped around Alicia's body atop a plain white tank top and embroidered pants, making her outfit seem thrown together and confusing. Swarovski crystals adorned her eyelids, but they might as well have been painted with melted gold because it wouldn't matter — nothing could make this look come together. The fashion faux pas landed Alicia on numerous worst dressed lists. But we're pretty sure she didn't care because Alicia does what she wants, regardless of what anyone else thinks (which is a look we love).
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The Grammys historically have included wacky fashion, and in 2019 it was Cardi B who made headlines for her bold sartorial selection. That year, the rapper arrived in this vintage Mugler gown from 1995– a black-and-pink shell-like design that she accessorized with pearls. It made fans go nuts and debate whether she was channeling an oyster or "The Little Mermaid" villain Ursula the sea witch.
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Kesha brought the house down with her powerful performance at the 2018 Grammys. But first, Janelle Monae introduced the singer, saying, "We come in peace, but we mean business… I am proud to stand in solidarity… with my fellow sisters in this room who make up the music industry. To those who would dare try and silence us, we offer you two words: Time's up," she said. "We say time's up for pay inequality, discrimination or harassment of any kind and time's up for abuse of power. It's not just going on in Hollywood… It's right here in our industry." Kesha then performed her powerful song "Praying" — which she wrote during her lengthy legal battle with producer and label exec Dr. Luke that started with her claims that he sexually assaulted her (which he's denied) — alongside Cyndi Lauper, Bebe Rexha, Camila Cabello, Julia Michaels, Andra Day and more. The performance was a tearjerker and prompted a standing ovation as Kesha sang her final note.
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The 2002 Grammy Awards featured a hilarious on-stage strip-down by host Jon Stewart. Poking fun at heightened security measures, Jon was searched by a wand-wielding guard (played by then little-known comedian Jimmy Kimmel) and forcibly stripped by two additional security guards, leaving him in his boxers in front of the audience. Before introducing the night's first two presenters, Jon said, "I don't think anyone was ready for this jelly."
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The reason that Sly Stone's appearance on stage at the 2006 Grammys was so buzzworthy was that he hadn't made any public appearances since 1993, when he was inducted into the Rock and Roll Hall of Fame. The founding member of the group Sly and the Family Stone appeared at the tail end of his group's performance that night, taking his place behind a keyboard, while the band — along with Maroon 5, Joss Stone, John Legend, will.i.am and Steven Tyler — sang "I Want to Take You Higher." Donning a platinum mohawk and a metallic jacket, the performer sang along for a few minutes before exiting the stage before the song was over.
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The night before the 2012 Grammy Awards, the music world took an unexpected hit when legendary singer Whitney Houston was found dead in her hotel bathtub from an apparent drug overdose. With little time to prepare, the Recording Academy made every effort to pay tribute to the fallen star, including with a gut-wrenching performance of Whitney's "I Will Always Love You" from Oscar-winning actress and singer Jennifer Hudson. No one in the audience (including Jennifer herself) had a dry eye as she belted out a flawless rendition of the song that made Whitney an icon so many years before.
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We dare you not to cry about this one. At the 2014 Grammy Awards, Macklemore and singer Mary Lambert performed their inspiring marriage equality song "Same Love." While that in itself is heartwarming, what happened next took our breath away: Presenter Queen Latifah emerged on stage as the song came to an end to announce that she was officiating the marriage of 33 gay and straight couples in the audience. As the camera zoomed out to capture all the beautiful couples on their wedding day, Madonna arrived to sing "Open Your Heart" to the beat of "Same Love" with Mary by her side. As the couples exchanged rings, we all felt the love.
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Just one year after taking part in the awe-inspiring Grammy Awards wedding ceremony, Madonna returned to the show in 2015 wearing a custom-made Givenchy matador outfit that also kind of looked like a naughty maid's uniform. While we're used to seeing Madge push the envelope when it comes to fashion, we weren't expecting her to flash the cameras as she walked by. Whether by mistake or design, Madonna lifted the tiny skirt from her rear and gave us all an admirable view of her assets.
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At the 1998 Grammy Awards, iconic singer Bob Dylan was performing his song "Love Sick" when a shirtless dancer named Michael Portnoy fluttered on stage writhing and jerking around to Bob's music with the words "Soy Bomb" written in bold black letters across his chest. It was clear that Bob had no idea who the guy was or why he was sharing the stage with him, but like a true professional, he kept right on singing, even after security shooed the stranger off stage. It was later revealed that Michael had been hired by the Grammys to dance and sway to the music while in the audience but had decided instead to host a mini-revolution by bombarding the stage. His explanation for "soy bomb" was less clear: "All art should be soy bombs," he said. Um, what?
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In 1984, pop singer Michael Jackson made Grammys history when he won an unprecedented eight awards — more than any artist ever at the time. Along with winning the album of the year prize for "Thriller," Michael also won best rock, R&B and pop vocal performance Grammys, among other awards. He even won in the best recording for children category for his work on the audiobook and soundtrack album for the 1982 blockbuster film "E.T. The Extra-Terrestrial."
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No one, however, does uncomfortable and awkward better than Kanye West. The multiple Grammy winner has a reputation for crashing other winners' acceptance speeches (cough, cough, Taylor Swift's 2009 MTV VMAs win) so it was almost no surprise when Kanye ascended the stage as Beck was announced as the winner of 2015's album of the year prize. Kanye approached the mic but then seemed to have second thoughts about it, so he merely shook his head and made a hand gesture before returning to the audience. Beck asked Kanye to come back but Kanye kept silent until after the ceremony, when he made it clear he felt Beyonce should have won instead. Three weeks later, Kanye apologized for his actions via social media.
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Crashing Grammy speeches isn't a Kanye West exclusive, it seems. Back in 1998 at the 40th Annual Grammy Awards, rapper ODB from the hip-hop group Wu-Tang Clan rushed the stage when singer Shawn Colvin was announced as the winner of the song of the year prize for her hit single "Sunny Came Home" (she also won for record of the year). ODB, who may or may not have been a little tipsy when he took the mic, talked about how great his group was and how he'd bought a new suit for the night because he'd expected Wu-Tang would win in their category — best rap album — though they lost to Diddy. Totally not embarrassing at all, right?
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Kendrick Lamar's multiple snubs in favor of Macklemore & Ryan Lewis at the 2014 Grammys became one of the most talked-about moments of the night. In fact, the wins were so controversial that it still makes fans angry today. Macklemore beat Kendrick in three rap music categories and bested him for best new artist, leading many to allege that the genre was being gentrified. Even Macklemore himself believed Kendrick should have come out on top. He later texted Kendrick, "You got robbed. I wanted you to win. You should have. It's weird and sucks that I robbed you."
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Never one to shy away from theatrics, rapper Nicki Minaj got sacrilegious with her 2012 Grammys appearance. She hit the red carpet in a devilish red hooded Versace ensemble with an elderly faux-Catholic bishop (or maybe he was a faux-Pope?) on her arm. Their entrance immediately raised eyebrows while setting the stage for Nicki's performance of "Roman Holiday," in which she enacted an exorcism. You know, normal everyday Grammys stuff. The Catholic League was understandably upset at Nicki and the Recording Academy for allowing the performance to air.
