How Could Grammy GOAT Taylor Swift Not Have Won Best New Artist Back in 2008? It’s Complicated

Gracie Abrams, Fred again.., Ice Spice, Jelly Roll, Coco Jones, Noah Kahan and The War and Treaty may be disappointed that they didn’t win the Grammy for best new artist on Sunday (Feb. 4), but they shouldn’t despair. No less a Grammy GOAT than Taylor Swift came up short when she was nominated in that category 16 years ago.

When Cyndi Lauper (who had won in the category in 1985) and Miley Cyrus (who won her first two Grammys just last night) announced the winner for best new artist at the 50th annual Grammy Awards on Feb. 10, 2008, the award went to the gifted but troubled Amy Winehouse.

Winehouse was widely expected to win. She went into the night with six nominations, more than any of the other best new artist nominees that year. Fellow nominee Feist had four, Ledisi had two and the two remaining nominees, Swift and Paramore, each had just that one nod.

The bookings on the telecast reflected the nominations. Winehouse was invited to perform two songs, “You Know I’m No Good” and “Rehab.” (The performance was beamed in by satellite from a London studio when a work visa for Winehouse to enter the U.S. didn’t arrive in time.) Feist performed her hit “1234” on the telecast. Swift wasn’t invited to perform on the show, but she did at least get to co-present an award (best rap/sung collaboration) with Juanes.

Winehouse won five awards on the night. In addition to best new artist, she won record and song of the year and best female pop vocal performance for “Rehab” and best pop vocal album for Back in Black. She was the fifth female solo artist to land five awards in one night, following Lauryn Hill, Norah Jones, Alicia Keys and Beyoncé.

Here’s the thing people sometimes forget: Awards are a snapshot in time. They can’t predict the future. Who could have known that Swift would build (and build and build) as an artist, demonstrating amazing resilience, determination, ambition, grit and focus? Who could have known that Winehouse’s career would come to a tragically premature end with her death at 27 in 2011?

Winehouse had fully broken through commercially and had shown her full creative potential by the time of Grammy voting that first year. Back to Black entered the Billboard 200 at No. 7 in March 2007 (ultimately peaking at No. 2 in the wake of the Grammys). “Rehab” reached No. 9 on the Hot 100 in June 2007, well before the voting period began.

Swift’s development took much longer. Her debut album, Taylor Swift, didn’t crack the top 10 on the Billboard 200 until November 2007 (when it was in its 55th week on the chart). It ultimately peaked at No. 5 in January 2008. Swift didn’t land her first top 10 hit on the Hot 100 (“Change”) until August 2008.

The situation with Swift and Winehouse is similar in some ways to the situation with the Carpenters and Elton John at the very first live Grammy telecast on March 16, 1971. Karen and Richard won best new artist, besting Elton, country crossover star Anne Murray, R&B and Broadway star Melba Moore and The Partridge Family, then winding up the first season of their hit TV series. At the time of voting, Carpenters were headed for their third smash hit in a row, with “For All We Know” following “(They Long to Be) Close to You” and “We’ve Only Just Begun.” At that same point, Elton had just landed his first top 10 hit, “Your Song.”

Carpenters went into Grammy night with four nods, plus an additional nod for Richard for his arrangement of “Close to You,” a little-known Bacharach-David song from 1963 that he turned into a standard, earning the respect of no less an arranger than Bacharach himself. By comparison, Elton had three Grammy nods that year.

Voters at the time of course could not have known that Karen would later develop an eating disorder that she would battle for the last eight years of her life, leading to her death at age 32 in February 1983. (Elton also battled personal demons, as he has freely acknowledged.)

All four of these artists were/are tremendous talents. It’s a shame that they have to be pitted against each other like this, but that’s the nature of awards.

The thing to remember is that all career trajectories are different. To look once more at the best new artist nominees from 16 years ago, Feist has yet to land another nomination after the four nods that greeted her breakout hit “1234.” Winehouse won just one more Grammy after her five-award sweep – a posthumous win for best pop duo/group performance in 2012 for “Body and Soul,” a collaboration with Tony Bennett. Ledisi didn’t finally win her first Grammy until 2021. Paramore has won three Grammys – best rock song for “Ain’t It Fun” nine years ago and two more just last night: best rock album for This Is Why and best alternative music performance for the title track.

Swift is now up to 14 Grammys. In 2010, she became the youngest artist to win album of the year (a record that has since been eclipsed by Billie Eilish). In 2016, she became the first woman to win album of the year twice as a lead artist. In 2021, she became one of just four artists to win album of the year three times. And last night she became the first artist to win four times in that category.

I guess the old saying is true: It’s not where you start, it’s where you finish.