Awards

Ranking the top five biggest Grammy Award upsets

From Prince losing Album of the Year for ‘Purple Rain’ to Steely Dan beating Eminem, we ranked the top five biggest Grammy upsets and losses to date.

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The 65th annual Grammy Awards are moving back to the Crypto.com Arena after taking place in Las Vegas back in 2022.

Although the venue has changed, the host hasn’t, as Trevor Noah will be taking the Grammy stage for the third year in a row.

The 2023 Grammy Awards will air Sunday, February 5, at 8 p.m. ET on the CBS television network. And just by the nominations and performances alone, viewers can be expecting a star and hit-filled night.

In honor of the upcoming 2023 Grammy Awards, here is our ranking of the top five biggest Grammy upsets and losses to date.

5. Steely Dan beats out Eminem and Radiohead

The ‘Reelin’ In the Years’ singer won Album of the Year at the 43rd Grammy Awards for his 2001 album ‘Two Against Nature’.

Although it was a good album which peaked at number six on the Billboard 200 chart and sold more than one million copies, Steely Dan shocked viewers when it won over Radiohead’s ‘Kid A’ and Eminem’s ‘The Marshall Mathers LP’.

4. Esperanza Spalding makes Best New Artist history

Getting nominated for Best New Artist is a goal that many singers and creators have, but for Esperanza Spalding she was not only nominated but also won the category in 2011.

Although this was an exciting moment for the ‘I Know You Know’ singer as she became the first jazz artist to win the award, viewers were confused and upset that she beat out her competition which included Drake, Florence + the Machine, Justin Bieber and Mumford & Sons.

3. Prince and Springsteen lose to Lionel Richie

All the artists nominated for Album of the Year in 1984/1985 were all strong contestants to win. The category included Tina Turner’s ‘Private Dancer’ and Cyndi Lauper’s ‘She’s So Unusual’.

But viewers were convinced that it would be a close call between Prince and the Revolution’s ‘Purple Rain’ and Bruce Springsteen’s ‘Born in the U.S.A’.

In the end the winner was Lionel Richie who took the Grammy’s top trophy for his album ‘Can’t Slow Down’.

2. Sinatra beats the Beatles’ ‘Revolver’ album

The Beatles had tough award year in 1965, but what really sealed the deal for their losses was when their 1966 classic ‘Revolver’ lost Album of the Year to Frank Sinatra’s ‘A Man and His Music’

Although Sinatra is a music icon the album that beat out the Beatles was made up of mostly re-recorded versions of songs he had previously released.

1. Jethro Tull won Best Hard Rock/Metal Performance

Between the nominees of Metallica, AC/DC, Jane’s Addiction, and Iggy Pop, viewers and music lovers were shocked when Jethro Tull won Best Hard Rock/Metal Performance for ‘Crest of a Knave’. With most upset coming from the fact that the album didn’t fit the hard rock or metal genres at all.

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