The 25 most surprising winners in Grammy history

From Jethro Tull to Ray Charles to Adele, the Academy has handed down some real head-scratchers over the years

Music Features Grammy
The 25 most surprising winners in Grammy history
From left: Lionel Richie at the 27th Annual Grammy Awards (Barry King/WireImage), Adele at the 59th Annual Grammy Awards (Kevork Djansezian/Getty Images), Beck at the 57th Annual Grammy Awards (Kevork Djansezian/Getty Images) Graphic: The A.V. Club

Part of following the Grammys—and perhaps even loving them—is realizing that the National Academy of Recording Artists and Scientists often doesn’t award the right artist or album. NARAS is keenly aware of this problem. That’s the reason why they’ve established backroom blue-ribbon committees: they want to make sure the broader group of voters won’t cast ballots for acts that would embarrass the organization as a whole.

And while the Grammys, which mark their 66th edition on Sunday night from Los Angeles, have been getting sharper about who they nominate and award in recent years, they still have a long history of surprises, upsets and straight up shockers, including legendary rockers like Jethro Tull and Steely Dan and one-hit wonders like The Starland Vocal Band and A Taste Of Honey. Here, ranked from 1 to 25, are the most surprising winners in the long history of the Grammy Awards.

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25 Comments

  • stevennorwood-av says:

    You seem to be largely begrudging people for being given awards, which is a shitty look. Especially in some of these cases where people were just as deserving as the competition. The Spalding slide makes it sound like since she wasn’t a household name someone else should have gotten the prize? You’re downplaying someone’s talent for clicks. That’s lousy.

  • thegobhoblin-av says:

    And the number one most surprising winner in Grammy history? You guessed it! Frank Stallone.

  • paulfields77-av says:

    I loved the fact that when Metallica won Best Metal Performance in 1992, they thanked Jethro Tull for not having put out an album that year.

  • paulfields77-av says:

    I also wouldn’t describe America as “British troubadours”.

  • runkevlarrun-av says:

    I’d love to know who the competition was a bit more – like 1981 Christopher Cross’ domination – thanks to Google – beating Billie Joel (Glass Houses) & Pink Floyd (The Wall); beating out the Pretenders in “new artist”, etc.

  • paulkinsey-av says:

    When the list of awful choices by Grammy voters is this long, it’s hard to call any of them surprises. The year Steely Dan won was when I realized that the Grammys were a joke and stopped caring about them.

    • thegobhoblin-av says:

      Sounds like somebody lost Rikki’s number back when they were reelin’ in the years.

    • bcfred2-av says:

      If you just assume that any legacy act that seems out of place among more contemporary nominees is going to win, you won’t ever be surprised or disappointed. There are obviously enough senior citizens among the voters to swamp the remainder who split votes among newer artists. Runner-up expectation goes to acts who at least sound like they could have been recording 40 years ago (Adele). It’s also why it really is a surprise when someone like Arcade Fire slips past the goalie.

    • Rev2-av says:

      Steely Dan was so far beyond the other acts and their album is so wonderfully written and recorded – I’m not surprised they won. They deserved it. 

    • xpdnc-av says:

      It’s the problem with all of the major awards. All too often, the award is for a body of work, not the individual performance that wins the award, leaving the better individual works in the category in the cold. Which then often leads to those artists getting an award later to make up for the oversight, leaving some other artists in the cold, perpetuating the error.

  • radioout-av says:

    I remember being a kid, maybe 8 or so when Afternoon Delight came out. I asked my dad what it was about…He said it was about eating ice cream.And 1978 was awful. You could not get away from Debbie Boone. Back when the blue law in MA and RI were in effect; we used to take Sunday drives (because everything was closed) and how many times did I sit in the of our Beetle and hear “You Light Up My Life”. Ugh. 

  • hornacek37-av says:

    Milli Vanilli should not be on this list because their win was not surprising. They were very popular and very successful. The only reason they’re on this list is that it was later revealed they lip-synched and weren’t the real singers, and had to return the Grammy. They should be on a “most undeserving winners” or “most scandalous winners”.

  • hornacek37-av says:
  • bs-leblanc-av says:

    I don’t think it’s very surprising that nearly half of these are Best New Artist awards. Even though the issue might be some artists weren’t “new” at the time, hindsight can definitely make new artists seem surprising or even overrated when you look back and their career might have fallen off after the Grammy.

  • blpppt-av says:

    “At least Tull has a real drummer.” — Grammy judges, 1989

    • thepetemurray-darlingbasinauthorithy-av says:

      Andre Agassi Foundation: “For a $35,000 donation, you can have an hour-long private drum lesson with Lars Ulrich!”Every metal fan: “It’s gonna take way more than a hour to teach Lars drums.”

      • blpppt-av says:

        Yep, I remember when he did that. Multiple variations of “I aint spending $30K to teach Lars how to drum!”

  • mikepencenonethericher-av says:

    According to the Grammy rules, “Our Best New Artist category probably has the most complicated set of rules of any of our categories. Essentially, a “new artist” is defined for the GRAMMY process as any performing artist or established performing group who releases, during the eligibility year, the recording that first establishes the public identity of that artist or established group as a performer.”So i suppose “first establishes public identify of that artist” gives them leeway? 

    • xpdnc-av says:

      I remember when Spaulding was the winner that the Bieber fans took it personally, behaving badly towards her.

    • thewayigetby-av says:

      Even with this parameter it’s still complete BS. The Chainsmokers were nominated for best new artists even though they already had a Top 40 song. 

  • sh90706-av says:

    That award for Jethro Tull was funny as well as embarrassing. Im a fan of Tull even still, but this is hardly heavy metal. Tull would have been a legit recipient back in about 1978 or so. Anyway, that’s all, Good day

  • bhlam-22-av says:

    I wouldn’t really call the Bon Iver or Arcade Fire win “upsets.” Bon Iver had two other general field nominations (both for “Holocene”) and was a favorite to win in Alternative Music Album. They were a huge deal at the time. The crazier thing is that Justin Vernon announced an indefinite hiatus just months later—although, they did come back and continue to rack up Grammy nominations.Arcade Fire is two things. First, they’re typically old heads. If there is a more conservative option, they’ll probably take it. In a field with Lady Gaga, Katy Perry, and Eminem, they’re far and away the most palatable option. Sure, Eminem was a veteran more or less, but NARAS avoids hip hop in the general field as often as they can. On top of that, they are arguably the definitive indie acts of the 2000s when “indie music” is becoming mainstream, even if they never had a crossover hit like Modest Mouse or Franz Ferdinand. The Suburbs was a critical and commercial hit—maybe not a blockbuster, but debuting at #1 on Billboard 200 still means something in 2010.

  • pitstopblog-av says:

    I will go outside the awards you listed and through out this one:
    Boxed or Special Limited Edition Package in 2019 going to Weird Al Yankovick.

  • mavar-av says:

    Don’t forget the musical genius of Dewey Cox

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