Grammy flashback: Kanye West and Amy Winehouse upset by Herbie Hancock in 2008, and maybe that was a good thing

Going through the list of previous Album of the Year Grammy winners, you’ll see some familiar faces. Taylor Swift and Adele pop up a couple times, you’ll see critically beloved records like Kacey Musgraves’s “Golden Hour” and Arcade Fire’s “The Suburbs,” some veterans like Robert Plant and Alison Krauss, as well as some big blockbusters like Santana’s “Supernatural.” But among those somewhat predictable picks over the last couple of decades, one sticks out immediately: Herbie Hancock for “River: The Joni Letters.” Now, if you’re on the younger side you might have no idea who Hancock even is, but if you were watching the 2008 Grammys then you were probably shocked by Hancock’s seemingly out-of-nowhere victory. Let’s take a look back.

Hancock is a jazz musician who’s considered one of the best in his genre. He’s worked with everyone from Miles Davis to Christina Aguilera, and became highly sought-after due to his prolific work. Prior to “River,” Hancock already had a good track record. He had won 10 Grammys prior, along with many other nominations going back to 1969. He had also won an Oscar more than 20 years before his Album of the Year Grammy win: Best Original Score for his work on “Round Midnight” (1986). So, needless to say, Hancock had the respect it took to overtake the big competition he had. And he definitely had some very big competition.

Amy Winehouse was a favorite to win that year. “Back to Black” was a massive success, launching Winehouse to international stardom and critical praise. Her song “Rehab” was nominated for Song and Record of the Year, and she was also pretty locked for Best New Artist. Another front-runner was Kanye West with “Graduation.” West was the biggest nominee of the year with eight bids, most of those in the rap field, and it was West’s third straight album to contend for Album of the Year. Additionally, Foo Fighters were nominated for “Echoes, Silence, Patience and Grace,” which contained the Record of the Year nominee “The Pretender.” Finally, Vince Gill’s “These Days,” which remains one of his most acclaimed records, was also nominated. So Hancock was up against a stacked field.

The night was shaping up to be Winehouse’s coronation. She ended up taking five trophies, including Best New Artist, Record of the Year, and Song of the Year. Not only that, but presenters Usher and Quincy Jones announced the winner of Producer of the Year right before they revealed the Album of the Year: a young, pre-“Uptown Funk” Mark Ronson, who produced Winehouse’s album. So it was a huge surprise when Jones (who looked delighted) announced Hancock as the winner. Hancock, clearly shocked too, hugged his producer Larry Klein and walked enthusiastically to the stage.

But as surprised as Hancock might have been, he was well prepared when he went up to that stage. He started his speech by highlighting how jazz has been underrepresented in the top categories at the Grammys, with “River” being the first jazz album to win Album of the Year in 53 years (“River” was the third jazz album to win, following “The Music From Peter Gunn” by Henry Mancini at the inaugural Grammys in 1959 and “Getz/Gilberto” by Stan Getz and Joao Gilberto in 1965). He then pointed out how his win was not only for him, but for the under-rewarded jazz giants that came before him, who never had the chance to win the award (especially Black jazz artists).

What truly shined in Hancock’s speech was a simple sentence: “Thank you to the academy for courageously breaking the mold this time.” Love it or hate it, it’s a fact that these awards can sometimes turn into a popularity contest, whether it is the bestselling albums of the year, or the most acclaimed, or a combination of both. Wins like “River’s” show us that sometimes the underdogs who don’t usually get a shot at glory deserve the spotlight. Earlier that night, all four other Album of the Year nominees had won in their respective genre categories, so as Usher said, there were “no losers” in that category. And seeing Hancock pull off an upset was not only a nice break from monotony, but also hopefully gave less mainstream artists the hope that, if a jazz musician can take out Kanye West and Amy Winehouse, perhaps they can win big too one day.

Hancock’s win remains, to this day, pretty relevant. He’s still the last Black artist to win the category, and he also remains the last jazz artist to win. But slowly we’ve seen jazz be more represented in the general field, whether it’s jazz-leaning Jacob Collier in Album of the Year for “Djesse Vol. 3” in 2021 or Esperanza Spalding upsetting Justin Bieber upset for Best New Artist in 2011. One can only hope that soon we can remember Hancock’s win as a great honor for a musical legend and not as a reminder of how much more Black and jazz artists deserve from the academy.

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