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21 Strangest Best New Artist Grammy Wins

A short history of the Grammys’ most bizarre honor

Grammy; Hootie; 1994

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Congratulations, young pop star! You have just won the Grammy Award for Best New Artist! Get ready for a long and fruitful career. Perhaps in the field of VCR repair or rotary-phone design. Maybe managing an Internet café? Let's face it, this Grammy goes to a lot of artists who never get heard from again, so don't worry too hard about Lorde. It's the notorious Curse of the Best New Artist. Winning the award can be a sign of impending doom — it's like the scene in a Mel Brooks movie where somebody says, "At least it's not raining."

But that's why Best New Artist is everybody's favorite Grammy category — it's the one with the most bizarro picks. Some years they give it to the Beatles, Mariah Carey or Adele. Other years it's the Starland Vocal Band, A Taste of Honey or Evanescence. And once it was Milli Vanilli. Nobody can predict these things. When Lily Tomlin presented the statue for Best New Artist of 1982, she said, "This award is not just for the new star of today, but for someone who just possibly may be a star for years to come." Then she gave it to Men at Work. That's how it goes when you bet on the rookies. Sometimes they score wildly successful debuts, then suddenly find themselves up the hootie without a blowfish.

So here's a salute to 21 awesomely weird BNA wins. (The pre-Beatle years don't count, unless you really want to argue about how Ann-Margret got robbed in 1962.) Some of these were surprise upsets. Others were total one-shot scams. And one was Milli Vanilli. But practically all of them gave the world a half-decent song or two, which is all you can ask of a pop star. Better one glorious moment than a career of mediocrity — that's what Best New Artist is all about. By Rob Sheffield

Amy Winehouse

C Brandon/Redferns

Amy Winehouse (2007)

Winehouse was made for the BNA award, and it was made for her. So young. So female. So singer-songwriter-y. Kinda like Taylor Swift, who was also nominated that year. Except the Grammy voters figured Winehouse was the more promising rookie, since she was the one with the tattoos, the English accent and the boyfriend in jail. ("For my Blake incarcerated!") Despite her outlaw rock cred, Winehouse was already essentially retired by the time she won. She lived another three and a half years, but released no new music in this time, while Swift kept writing truckloads of great songs. By the time of Winehouse’s tragic death in 2011, Swift had already made another two blockbuster albums, Fearless and Speak Now.

Bon Iver

Kevork Djansezian/Getty Images

Bon Iver (2011)

Has anyone looked so tortured at the idea of winning a Grammy? (And he refused to participate in the ceremony's Beach Boys homage. Go get 'em, tiger.) Justin Vernon may be the most obscure artist to get nominated for BNA, much less win, but that just makes him part of this gloriously nonsensical Grammy tradition. And his finest song, "Beth/Rest," sounds exactly like Christopher Cross, so this means a de facto second Best New Artist win for C.C. Always bet on Christopher Cross. Always.

Macklemore & Ryan Lewis

Macklemore (R) and Ryan Lewis pose with their awards in the press room during the 56th Grammy Awards at the Staples Center in Los Angeles on January 26, 2014. AFP PHOTO/Joe KLAMAR (Photo credit should read JOE KLAMAR/AFP/Getty Images)

Joe Klamar/Getty

Macklemore & Ryan Lewis (2014)

Most years it'd look bizarre if Macklemore & Ryan Lewis didn't win Best New Artist after the blockbuster rookie season they had. But most years don't have Kendrick Lamar as the competition. The entire slate of nominees was uncommonly strong that year: Kacey Musgraves, Ed Sheeran, James Blake. But as strong as all these artists are, there's only one Kendrick, as To Pimp a Butterfly made clear. Macklemore also won Best Rap Album and even he thought it was nuts — to his credit, he sent Kendrick a text that night: "You got robbed. I wanted you to win. You should have."

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