9 Most Surprising Grammy Wins of All-Time

It’s no surprise when award shows spark debates among fans and industry professionals, but sometimes the result is so unexpected that it’s hard to imagine how things even turned out this way. That has been the case at the Grammy Awards several times, and these awards only get more surprising in hindsight. While musical taste is definitely subjective, there have been some Grammy winners in recent years that surprised just about everyone.

The Grammys are decided by the Recording Academy – a nonprofit organization made up of professionals in the music industry. They are the most prestigious award in the music industry, but the nomination and voting processes are hard to understand, leaving room for rumors and allegations of cheating. This has been the case in recent years, especially after some prominent artists accused the academy and its internal committees of valuing money or influence over artistic merit. Fans have also taken up these cases on social media, and sometimes they use a seemingly unlikely win as evidence.

The Recording Arts Academy, which votes on the nominees, is often accused of following trends and mistreating artists. Musicians generally write and perform their work from top to bottom, so a snub at the Grammys can feel more personal than a snub at the Oscars for an actor. Other times, fans feel that the academy is missing the cultural significance of some piece of music or overvaluing that of another. Again, it’s a subjective award.

Yet when the general populous disagrees with the academy, it’s always clear. In today’s day and age, fans make themselves heard, and they’re not shy about telling music professionals that they’re wrong in their choices. The 2024 Grammys will air live on Sunday, Feb. 4 at 8 p.m. ET on CBS, and will stream simultaneously on Paramount+. In the meantime, here’s a look back at some of the Grammy wins that have shocked fans the most.

Macklemore, 2013

Macklemore took home the Grammy Award for best rap album in 2013 for The Heist, and the Seattle-based rapper looked a bit awkward on stage. Most people, including Macklemore himself, was in consensus that Kendrick Lamar’s Good Kid, M.A.A.D. City should take that award home.

Later on, Macklemore actually posted his text to Lamar on Instagram. “You got robbed,” he wrote. “I wanted you to win. You should have. It’s weird and sucks that I robbed you. I was gonna say that during the speech. Then the music started playing during my speech, and I froze. Anyway, you know what it is. Congrats on this year and your music. Appreciate you as an artist and as a friend. Much love.”

Lamar addressed the situation a few weeks later in an interview with Billboard, saying “That text surprised me, but Macklemore is a genuine dude. However it panned out, I wish him much success. He touched people’s souls, and no one can take that away. Really, the whole Grammy moment was incredible. Not everyone gets that shot.”

Adele, 2017

Adele’s 25 won album of the year in 2017, an honor that many fans felt should have gone to Beyonce’s Lemonade. Of course, Queen Bey didn’t let it bother her, but the uproar from the masses was staggering. Adele herself seemed to agree with them, as she said in her acceptance speech.

“I can’t possibly accept this award, and I’m very humbled and very grateful and gracious but my artist of my life is Beyoncé, and this album for me, the Lemonade album is just so monumental,” the singer said through tears in her acceptance speech. “Beyoncé, it was so monumental and so well thought-out and so beautiful and soul-baring, and we all got to see a side of you that you don’t always let us see and we appreciate that, and all us artists here 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.”

Beck, 2015

In 2015, Beck looked shell-shocked as he took the stage to accept album of the year for Morning Phase. He beat out Beyonce’s self-titled record, Ed Sheeran’s X, Sam Smith’s In The Lonely Hour,and Pharrell Williams’ Girl. That wasn’t the most surprising part of the win, however.

Kanye West followed Beck up onto the stage, an expression of mock anger on his face. The rapper famously interrupted Taylor Swift’s acceptance speech at the 2009 MTV Video Music Awards, and he seemed to be making fun of himself in the moment of that surprise upset. Beck didn’t even seem to be hurt by the implication, he asked West to come back up on stage to spare him from having to make an acceptance speech he clearly wasn’t planning on making.

Bon Iver, 2012

The acoustic crooning act was awarded both best new artist and best alternative music album at the 2012 Grammys, and while the academy was in agreement about his merits, many listeners hadn’t even heard of him yet. They had, however, heard of Frank Ocean, The Lumineers, Hunter Hayes, Fun and Alabama Shakes, all of whom Bon Iver beat. Justin Vernon, the band’s frontman, admitted it felt awkward to stand on stage and accept the honors.

“It’s really hard to accept this award,” Vernon said. “There’s so much talent out here … and there’s a lot of talent that’s not here tonight. It’s also hard to accept because you know, when I started to make songs I did it for the inherent reward of making songs, so I’m a little bit uncomfortable up here.”

Esperanza Spalding, 2011

The best new artist category in 2011 was filled with names that are now as famous as it gets. Justin Bieber, Drake, Florence + The Machine and Mumford & Sons were all up for the award, but it was jazz musician Esperanza Spalding who took home the golden gramophone.

Spalding was the first jazz musician ever to win in that category, and she was as flabbergasted as anyone. The pleasant surprise had some unwanted side effects, however, as Spalding received thousands of hateful messages from feverish Bieber fans in the following weeks.

Herbie Hancock, 2008

Herbie Hancock won best album of the year in 2008 for River: The Joni Letters, which was his ode to Joni Mitchell. No one particularly disliked the record, they were just surprised that Hancock triumphed over the stiff competition. That year, he was up against Kanye West’s Graduation, and Amy Winehouse’s Back to Black.

Jethro Tull, 1989

In 1989, the category of “best hard rock/metal performance, vocal or instrumental” was brand new, and fans were fairly certain Metallica would take the trophy home for …And Justice For All. Apparently, the academy hadn’t yet quite nailed down what “metal” was, as they gave the award to Jethro Tull for Crest of a Knave.

Just last year, frontman Ian Anderson spoke with EonMusic about the odd win. “We were nominated in that year strangely, in what was a new category,” he recalled, “and whilst we knew that we could not be classed as ‘hard rock,’ let alone ‘metal,’ it was a nomination that just seemed to sneak under the radar.

“The record company said they didn’t think it was really worth the expense of flying us over to Los Angeles because Metallica were favorites to win it, which suited me fine because we were working in the studio at that time.”

DJ Jazzy Jeff and The Fresh Prince, 1992

Will Smith, performing as The Fresh Prince, and his collaborator DJ Jazzy Jeff were given the Grammy for best rap performance by a duo or group in 1992 for their single, “Summertime.” The song has a nostalgic power that persists to this day, but many fans, especially hip-hop fans, thought it overlooked a much more important album that year.

Public Enemy’s Apocalypse 91… The Enemy Strikes Black was a politically charged powerhouse that hip-hop heads thought better represented the art form’s successes and triumphs.

Eric Clapton, 1993

Eric Clapton took home an armful of Grammy Awards in 1993, but the big surprise came when the MTV Unplugged version of his 1970 Derek & the Dominos song “Layla” won Best Rock Song over Nirvana’s “Smells Like Teen Spirit.” The young grunge band had blown up that year, and everyone expected them to be honored for their achievements, but the academy valued Clapton’s ongoing work in the genre.

Of course, Nirvana did just fine without the Grammy that year, and 25 years later, “Smells Like Teen Spirit” stands the test of time, while that particular version of “Layla” isn’t discussed much at all.