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The 15 unlikeliest Grammy winners ever

The Grammy Awards are, in a word, capricious. As soon as you think you can predict an award winner, you'll blink and they've awarded Artist of the Year to an indie band, or a jazz musician, or a four-piece pan flute band. 

It's worth remembering that decisions on who to award Grammy awards to aren't supposed to be based on popularity or chart position. It's meant to be a meritocracy. Even still, there have been some truly surprising Grammy winners across the years. Here are 15 of them.

 
1 of 15

2011: Arcade Fire wins Album Of The Year

2011: Arcade Fire wins Album Of The Year
Billboard

Most of us probably thought 2011 was a two-horse race between Katy Perry's "Teenage Dream" and Lady Gaga's "The Fame," with Perry leading the way on the strength of her pop chops. Then the Grammys went indie. Arcade Fire's brilliant album "The Suburbs" took home top honors, and caused a veritable deluge of "Who the heck is Arcade Fire?" tweets.

 
2 of 15

1979: A Taste of Honey wins Best New Artist

1979: A Taste of Honey wins Best New Artist
New York Times

In a nominee class that included Toto, The Cars, and the now-legendary Elvis Costello, nobody could have predicted that A Taste of Honey would take home the Best New Artist award at the 1979 Grammy Awards.

Compounding this issue was the fact that although it wasn't quite completely dead yet, disco was on its way out by 1979. Sure, "Boogie Oogie Oogie" was (and is) a great song, but it remains incredibly surprising that A Taste of Honey toppled the competition.

 
3 of 15

2008: Herbie Hancock wins Album Of The Year

2008: Herbie Hancock wins Album Of The Year
Ace Showbiz

This one really came out of nowhere. Sure, Herbie Hancock was (and still is!) a legend, and "River: The Joni Letters" is a beautiful album that was overlooked when it was released, but in 2008, he was up against Kanye West's "Graduation" and Amy Winehouse's "Back to Black". Suffice it to say, if you bet on the Album Of The Year award winner back in 2008, you were not a happy camper. Also, you might have a gambling problem.

 
4 of 15

2001: Steely Dan wins Album Of The Year

2001: Steely Dan wins Album Of The Year
Rolling Stone

Other nominees for the Album of the Year award back in 2001 included "Kid A", arguably the best Radiohead album ever released, a Beck album, Paul Simon's "You're The One", and an LP by an up-and-coming rapper named Marshall Mathers. Somehow, Steely Dan's "Two Against Nature" took home top honors against all four of them. Top music historians are still attempting to figure out exactly how they did it, since it makes no sense.

 
5 of 15

1985: Lionel Richie wins Album Of The Year

1985: Lionel Richie wins Album Of The Year
Spin

I want to start off by saying that this in no way is an indictment of Lionel Richie, or "Can't Slow Down", which is a great album in its own right. But of the six nominees for Album of the Year award back in 1985, Lionel Richie's record was probably the fifth least likely to win.

The field included "Private Dancer" by Tina Turner, Bruce Springsteen's "Born in the USA", "Let's Dance", by David Bowie, and a little known record called "Purple Rain" by Prince.

Say what you want about Richie, but it's pretty unbelievable that he won the award that year.

 
6 of 15

2011: Esperanza Spalding wins Best New Artist

2011: Esperanza Spalding wins Best New Artist
The Grammy Awards

Here, in no particular order, is a list of four artists who never won a Grammy award for Best New Artist: Drake, Mumford & Sons, Florence + The Machine, and Justin Bieber.

These acts had the misfortune of being nominated for the award in 2011, the same year the hyper-talented jazz musician Esperanza Spalding was up for the award. Though she may have been the best musician of the bunch that year, it was very surprising that the award wasn't given to one of the more popular, established acts on the list.

 
7 of 15

2014: The Civil Wars win Best Country Duo/Group Performance

2014: The Civil Wars win Best Country Duo/Group Performance
The Grammys

The Civil Wars have long been indie darlings, making folksy music for people who are partial to flannel shirts and beards. But in 2014, they were finally nominated for a Grammy award in the country genre. 

Fans of the band probably thought it was a nice nod to the band and nothing more. After all, how could they win against a Kenny Rogers/Dolly Parton duet, a Taylor Swift/Keith Urban collaboration, and a song by Little Big Town?

Well, the envelope was opened, and against all odds, they did, causing Civil Wars fans across the country to crack open their best tin of artisanal mustache pomade in celebration.

 
8 of 15

2010: The Kings of Leon win Record of the Year

2010: The Kings of Leon win Record of the Year
The Grammy Awards

Sure, "Use Somebody" was a hit back in 2009, but the simple fact is that Taylor Swift's "You Belong with Me", The Black Eyed Peas's "I Gotta Feeling", Lady Gaga's "Poker Face", and Beyonce's "Halo" were all bigger hits. Despite all that, the Grammy went to Kings of Leon anyway. Perhaps there was a bit of a pop overload that year.

 
9 of 15

1981: Christopher Cross wins Record Of The Year

1981: Christopher Cross wins Record Of The Year
Nolan Dalla

Let's play a little game here. Think of five Frank Sinatra songs. Got them? Okay, good. 

Is one of those songs "New York, New York?" Yeah, I thought so. Back in 1981, that song, as well as Kenny Rogers' "Lady," Bette Midler's "The Rose," and Barbra Streisand's "Woman in Love" all lost to "Sailing" by Christopher Cross, the undisputed king of unlikely Grammy winners. Don't worry, we'll come back to him later.

 
10 of 15

1966: Tom Jones wins Best New Artist

1966: Tom Jones wins Best New Artist
Scoopnest

At first blush, this doesn't seem all that unlikely, but then you read the list of nominees. Sure, there are some acts that have been forgotten to time (like Herman's Hermits), but the list of nominees also included Sonny & Cher and The Byrds, two of that era's biggest, most popular artists. 

Again, no disrespect to Tom Jones, but nobody could have guessed that he would snag the award over both Sonny & Cher and The Byrds.

 
11 of 15

1980: Rickie Lee Jones wins Best New Artist

1980: Rickie Lee Jones wins Best New Artist
Billboard

I'm going to apologize in advance, because "My Sharona" is about to be stuck in your head. Sorry about that. 

Back in 1980, the smart money was on Dire Straits to win Best New Artist, with the possibility of a mild upset courtesy of The Knack.

Instead, Rickie Lee Jones took the award home on the strength of her eclectic singer-songwriter chops.

 
12 of 15

1992: Marc Cohn wins Best New Artist

1992: Marc Cohn wins Best New Artist
AZ Central

Okay, I hear you. "Walking in Memphis" is a great song. Even so, it's incredibly surprising that in 1992, a year that saw Boyz II Men, C+C Music Factory, Color Me Badd, and Seal(!) nominated for Best New Artist, he was able to take home the award. All four of those other artists had huge hits that year, and though maybe Cohn's win isn't as surprising as others on this list, it was still a long shot.

 
13 of 15

1991: "Please Hammer, Don't Hurt 'Em" gets nominated

1991: "Please Hammer, Don't Hurt 'Em" gets nominated
All Music

Okay, bear with me. I know we're bending the rules for this one, since MC Hammer didn't end up winning the award, but in terms of surprising Grammy picks, we wouldn't be doing our jobs if we didn't at least mention this.

Yes, in 1991, MC Hammer was nominated for a Grammy award for his album "Please Hammer, Don't Hurt 'Em". He was nominated alongside Pariah Carey, Wilson Phillips, Phil Collins, and Quincy Jones (who ended up winning). 

This bears repeating. In 1991, "Please Hammer, Don't Hurt 'Em" was nominated for Album of the Year.

 
14 of 15

2002: "O Brother, Where Art Thou?" wins Album Of The Year

2002: "O Brother, Where Art Thou?" wins Album Of The Year
The News & Observer

This one was a pleasant surprise. In 2002, albums from Bob Dylan, U2, and OutKast were nominated alongside the wonderful soundtrack to "O Brother, Where Art Thou?" 

Many assumed that strong efforts from acts that were already established in the industry would take home the award for Album of the Year, especially given the fact that in retrospect, both "Stankonia" and "All That You Can't Leave Behind" have endured. But in a surprising upset, the Grammy went to the Soggy Bottom Boys.

 
15 of 15

1981: Christopher Cross Wins Album Of The Year

1981: Christopher Cross Wins Album Of The Year
Cracked

We told you we'd be back to this guy. In 1981, Cross's album "Christopher Cross" was up for album of the year alongside, well, one of the best albums ever recorded. 

You already know how this story ends. Cross won the award, beating out Pink Floyd's "The Wall" (and somewhat less egregiously, Billy Joel's "Glass Houses"). If you're looking to me to explain how or why this happened, well, sorry. I've got nothing. This is probably the most surprising win ever in the history of the Grammy awards, and also the most egregious looking error by the awards committee in retrospect.

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