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The 24 Most Shocking Grammy Moments of All Time

From "Soy Bomb" to Jennifer Lopez's iconic dress, these are the most memorable Grammy moments.

Even if you're not familiar with all of this year's Grammy nominees, you're likely to tune into the ceremony just to catch the surprising scenes that always seem to unfold. Whether it's the infamous Bob Dylan "Soy Bomb" dancer, Jennifer Lopez wearing one of the most iconic dresses in fashion history, or baffling wins—drama and the Grammys go hand in hand. In order to prepare you for the 2020 Grammy Awards on Jan. 26, we've rounded up the most shocking Grammy moments ever. See how many of these moments, which range from the awkward to the thrilling, you remember.

Bob Dylan gets "Soy Bomb"-ed.

bob dylan performing alongside soy bomb dancer at the grammys
CBS via YouTube

In one of the most bizarre awards show moments ever, Michael Portnoy stole the spotlight from Bob Dylan during Dylan's performance at the 1998 Grammys.

Portnoy was hired to be one of the extras grooving behind Dylan during his performance. Instead, he rushed the front of the stage, ripped off his shirt to reveal the words "Soy Bomb" on his chest, and was removed relatively quickly.

Portnoy later explained that "Soy Bomb" was a two-word poem, with soy representing "dense nutritional life" and bomb reflecting an "explosive destructive force." He added that "soy bomb is what I think art should be: dense, transformational, explosive life." Of course, that explanation doesn't make this Grammys moment any less shocking.

Beck wins over Beyoncé.

Beck musician Biggest grammy shockers

In one of the biggest upsets in the history of the Grammys, Beck shocked everyone when he won Album of the Year in 2015 for Morning Phase over Beyoncé's self-titled album.

It spawned a heated conversation about race at the Grammys, which reared its head again when Adele beat Beyoncé in 2017 for Album of the Year.

Shortly after the upset, even Beck told Us Weekly, "I thought she was going to win. Come on, she's Beyoncé!"

And Kanye West almost pulls a Kanye West.

Kanye West celebrity rider

Beck's win especially shocked Kanye West. But, unlike his interruption of Taylor Swift at the 2009 MTV Video Music Awards, he really did let Beck finish.

West rushed the stage, but then decided against it and sat back down. He saved his words for later that night. At an afterparty, West told E! News, "If they want real artists to keep coming back, they need to stop playing with us … Beck needs to respect artistry, and he should've given his award to Beyoncé."

Beck wasn't too upset by West's almost-interruption. He told Us Weekly, "I was just so excited he was coming up. He deserves to be onstage as much as anybody. How many great records has he put out in the last five years, right?"

Eventually, West apologized, but Beyoncé still hasn't won Album of the Year.

Jethro Tull beats Metallica for the first heavy metal Grammy.

Jethro Tull Biggest grammy shockers

When folk rockers Jethro Tull beat out Metallica for the Best Hard Rock/Heavy Metal Recording Grammy in 1989, you could hear a pin drop. Alice Cooper, who presented the award, remembered, "There was a two-minute pause, then everybody broke out laughing. They thought I was doing a joke. I said: 'No, I'm not kidding. Jethro Tull.'"

Not only did Jethro Tull beat out Metallica, the most prolific heavy metal band of the 20th century, but they also won over Jane's Addiction, Iggy Pop, and AC/DC.

It was particularly surprising since this was the first year that the National Academy of Recording Arts and Sciences decided to hand out the new award in an effort to recognize contemporary music. Never again have "Jethro Tull" and "heavy metal" appeared in the same sentence.

Frank Sinatra gets cut off, and Billy Joel takes a stand.

older frank sinatra performing

When Frank Sinatra was honored at the 1994 Grammys with the Legend Award, his speech seemed to go on and on. But no one expected the broadcast to cut him off mid-sentence and immediately go to commercial.

Later during the ceremony, Billy Joel took a stand. He stopped his performance of "River of Dreams" intentionally to waste commercial time, saying, "Valuable advertising time going by. Dollars, dollars, dollars." He smirked, and carried on.

Jennifer Lopez wears a barely-there dress.

Jennifer Lopez green versace dress Biggest grammy shockers

It's impossible to forget the tropical sheer Versace dress Jennifer Lopez wore to the 2000 Grammys.

It was the most-searched item on the internet for weeks and it directly inspired Google to launch Google Image Search. The company's former executive Eric Schmidt was quoted as saying, "At the time, [the dress] was the most popular search query we had ever seen. But we had no surefire way of getting users exactly what they wanted: J­Lo wearing that dress." Enter Google Image Search.

Esperanza Spalding wins a Grammy and people learn her name.

Esperanza Spalding Biggest grammy shockers

Not even Esperanza Spalding saw her 2011 Best New Artist Grammy coming—and neither did the majority of music fans, most of whom had never heard of her. "I certainly did not expect to even be considered for that type of nomination, me being a little old jazz musician," Spalding told Entertainment Weekly.

She beat out heavy hitters like Drake, Justin Bieber, Mumford & Sons, and Florence + The Machine for the title. And suddenly, Spalding, too, became a hot Google search.

Milli Vanilli's Grammy gets taken away.

milli vanilli performing
dpa picture alliance / Alamy Stock Photo

In a first for the Grammys, the National Academy of Recording Arts and Sciences rescinded Milli Vanilli's 1990 Best New Artist Award after it was revealed that the duo did not sing any of the vocals on their album All or Nothing, including their hit, "Girl You Know It's True." That's not the kind of history any artist wants to make.

"I hope this revocation will make the industry think long and hard before anyone ever tries to pull something like this again," recording academy president Mike Greene said at the time. Seemingly, it has.

Ol' Dirty Bastard interrupts Shawn Colvin.


When Wu-Tang Clan lost Best Rap Album to Puff Daddy at the 1998 Grammys, Ol' Dirty Bastard was so fed up that he stormed the stage, but not even during Puffy's acceptance speech.

He took the mic when poor Shawn Colvin, who won Song of the Year for "Sunny Come Home," was making hers.

As he hijacked the moment, ODB pointed out that he'd helped save a child that week and that his clothes for the ceremony cost a lot of money. Eventually, he gave the mic back to Colvin, who got to finish her speech.

M.I.A. performs while very pregnant.

m.i.a. performing

Just how close to giving birth was M.I.A. when she performed her hit song "Swagga Like Us" at the 2009 Grammys? She was quite literally having contractions while she moved around effortlessly onstage.

Her fellow performers—Jay-Z, Kanye West, Lil Wayne, and T.I.—could never.

Herbie Hancock wins Album of the Year over Amy Winehouse.

Herbie Hancock Biggest grammy shockers

Accomplished jazz musician Herbie Hancock looked shocked when his Joni Mitchell covers album, River: The Joni Letters, beat out Amy Winehouse's critically acclaimed Back to Black for Album of the Year in 2008.

Winehouse still scored five Grammys, but it's hard to rationalize an album of covers beating instantly iconic original music.

Madonna shows off her assets.

Madonna red carpet style fails

Madonna has left audiences' jaws on the floor for decades, but she proved she still had it at the 2015 Grammys, when she stepped onto the red carpet in lingerie that left little to the imagination.

She even flashed her derrière for photographers to capture. At 57 years old, she proved she could be as provocative as ever.

Helen Reddy calls God a "she."


So many awards winners thank God, especially at the Grammys, that it was no surprise when Helen Reddy won Best Female Pop Vocal Performance at the 1973 Grammys and did the same.

The only difference? She called God a "she." "I would like to thank Jeff Wald, because he makes my success possible, and I would like to thank God because She makes everything possible," Reddy said.

It might have been shocking to hear at the time, but it really wasn't that unexpected: The Aussie singer won for her song "I Am Woman," which became an anthem for second-wave feminism in the 1970s.

Annie Lennox fools everyone in drag.

Kathy Hutchins/Shutterstock

Annie Lennox arrived at the 1984 Grammys in head-to-toe drag, ready to perform "Sweet Dreams (Are Made of This)."

The only problem? Producers were panicking looking for her backstage seconds before the performance, because they didn't recognize her in her suit and mutton chops. "People were unaware that it was me," Lennox later told CTV News. "So it was almost like being a fly on the wall for awhile."

Eventually, Lennox took the stage, and it took audiences a bit to figure out what was happening. "If ever you get a chance to perform on live television, you have an opportunity to make something special because millions of people will be watching you," Lennox said. Well, she certainly capitalized on that opportunity.

Jennifer Hudson pulls off a last-minute Whitney Houston tribute.

Shutterstock/lev radin

Legendary artist Whitney Houston was found dead in her Beverly Hilton hotel room hours before the 2012 Grammy Awards festivities began. Her death left the music world in mourning, and Grammy producers wondering how to pull off a tribute with hardly any time at all.

Jennifer Hudson was a last-minute addition to the 2012 Grammys roster, and she boldly performed "I Will Always Love You" in honor of the late Houston. Nothing could have made up for the staggering loss of Houston, but Hudson brought the house down with her vocals, and we all had chills.

Christopher Cross takes Sinatra's gold.

Christopher Cross Biggest grammy shockers

At the 1981 Grammys, it came as a complete surprise when Christopher Cross won Album of the Year and Record of the Year over Ol' Blue Eyes himself. Yes, you read that right. Cross' "Sailing" beat out Sinatra's "Theme From New York, New York" for Record of the Year.

Good luck explaining that one.

Kristen Wiig dons a Sia wig.

kristen wiig on the red carpet
Shutterstock/Kathy Hutchins

It wasn't surprising to see Maddie Ziegler onstage alongside Sia during the 2015 Grammys performance of Sia's hit song "Chandelier": Dance Moms alum Ziegler had already appeared in the music video.

But Kristen Wiig's appearance—in full Sia drag, no less—was a pleasant (and baffling) surprise. Ultimately it was as funny as it was confounding.

Justin Timberlake makes an awkward apology for Super Bowl "Nipplegate."

Justin Timberlake
Shutterstock/Denis Makarenko

We probably don't need to remind you about the time Justin Timberlake ripped Janet Jackson's top and exposed her nipple jewelry at the 2004 Super Bowl half-time show. But you may not remember Timberlake's public apology for the "wardrobe malfunction" at the 2004 Grammys. That's because you wouldn't want to.

When he won Best Male Pop Vocal Performance for his hit song "Cry Me a River," Timberlake gave an incredibly awkward acceptance speech.

"I know it's been a rough week on everybody," he said with a smirk. "What occurred was unintentional, completely regrettable, and I apologize if you guys were offended." Rough, indeed.

Pink leaves jaws dropped with her acrobatics.

top-earning celebs

Pink has had many impressive performances in her 20-year career. But the most iconic was her rendition of "Try" at the 2014 Grammys, where she hung over the crowd and sang live while doing incredible acrobatics on a rope without a harness.

It was shocking in the best way possible. She didn't win a Grammy that year, but the performance alone was award-worthy.

50 Cent makes a silent protest against Evanescence.

50 cent celebrity pets
Jamie Lamor Thompson/Shutterstock

At the 2004 Grammys, 50 Cent wasn't happy Evanescence beat him out for Best New Artist. So, he pulled a Kanye and jumped up onstage as the band's lead singer, Amy Lee, started giving her acceptance speech.

"We all thought that 50 Cent was going to win Best New Artist. I think everybody did," Lee later said. "When 50 Cent started walking toward the stage in the middle of my acceptance speech, it seemed exactly like that moment in Zoolander where Hansel wins the modeling award, but Derek is so sure that he's going to win he doesn't notice they called the other guy's name."

Lee still isn't sure if 50 Cent was "planning to say something and then chickened out, or he did it to win a bet or something." But, she added, "It just made a crazy moment even crazier."

Twenty One Pilots accept a Grammy in their underwear.

Twenty One Pilots Biggest grammy shockers
CBS via YouTube

Upon receiving their Grammy for Best Pop/Duo Performance for "Stressed Out" at the 2017 Grammys, Twenty One Pilots walked up onstage to accept the award in their underwear.

According to the band, it was fulfilling an old promise that they made to each other to accept their first Grammy clad only in their skivvies.

Host James Corden followed suit, introducing Ed Sheeran in his boxer briefs as he explained to the audience, "I always told myself that if I ever hosted the Grammys, I would also do it in my underwear."

Elton John and Eminem perform together.

Elton John and Eminem Biggest grammy shockers
CBS via YouTube

The beginning of Eminem and Elton John's strange friendship began with their performance of the rapper's song "Stan" at the 2001 Grammys. It was eye-popping to see, considering that John was an openly gay artist and activist, and Eminem's lyrics had been widely criticized for their homophobic vitriol.

"I didn't know he was gay. I didn't know anything about his personal life. I didn't really care," Eminem told MTV News in 2004. "But being that he was gay and he had my back, I think it made a statement in itself saying that he understood where I was coming from."

Lady Gaga arrives in a giant egg.

lady gaga inside an egg being carried into the grammy awards on the red carpet

Lady Gaga has never been afraid to show her stranger side, but she really outdid herself at the 2011 Grammys when she showed up in an egg carried by four people in skimpy outfits.

She did not emerge from said egg until her performance of "Born This Way" later in the evening. At the very least, you have to commend her commitment to her art.

Chris Brown and Rihanna bow out of their Grammys performances after an ugly domestic dispute.

chris brown on the red carpet

Just hours before they were each set to perform at the 2009 Grammys, Chris Brown turned himself in for beating his then-girlfriend Rihanna.

The violent assault occurred shortly after the couple appeared smiling together at a pre-Grammys party. Neither attended the Grammys, as Rihanna was in the hospital and Brown was arrested, but the shocking news rocked everyone to their core. Eventually, Brown was sentenced to community labor, five years of probation, and one year of domestic-violence counseling.

Ashley Moor
Ashley hails from Dayton, Ohio, and has more than six years of experience in print and digital media. Read more
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