Peter Macdiarmid/Getty; Dan MacMedan/Wireimage
Alex Heigl
February 04, 2015 06:20 AM

The Best New Artist Grammy is perennial fodder for think pieces, mostly because for every time the award has gone to a new artist who then gains fame and fortune, there’s another that’s gone to people who – perhaps sadly, perhaps deservedly – had somewhat truncated careers.

Hindsight is, after all, 20/20. Check out a handful of those Best New Artist head-scratchers below.

The Winner: Robert Goulet (1963)

The Upset: The Four Seasons; Peter, Paul & Mary
Nothing against Robert Goulet, but when you search his name, one of the most common results is Will Ferrell’s impression of him. Whereas The Four Seasons sold about a bajillion records and had a hit Broadway musical and a movie made about them and Peter, Paul & Mary weren’t slouches, either.

The Winner: Jose Feliciano (1969)

The Upset: Cream
Jose Feliciano is certainly talented, but most people know him primarily for “Feliz Navidad,” which is one of the reasons we start dreading the holiday season. Cream, on the other hand, sold out four Madison Square Garden shows in an hour almost 50 years after they broke up.

The Winner: America (1973)

The Upset: The Eagles
America has that one song about a horse and then another equestrian-themed album, the soundtrack to The Last Unicorn. The Eagles, by contrast, are the only recording artists in history with three albums that have each sold over 10 million copies. But in 1973, it was anybody’s game.

The Winner: A Taste of Honey (1979)

The Upset: The Cars, Elvis Costello
“Boogie Oogie Oogie” is a great song, no denying it. But up against two of the most influential artists of the “new wave” era? A Taste of Honey hasn’t aged so well.

The Winner: Rickie Lee Jones (1979)

The Upset: Dire Straits
To be fair, no one looked at Dire Straits and Jones in 1979 and thought, “That gangly bunch of dudes led by a finger-style guitar virtuoso really has something over this cute jazzy crooner.” Then, a few years later, Dire Straits had “Romeo and Juliet” and “Money for Nothing” under its belts, and suddenly things looked a little bit different.

The Winner: Marc Cohn (1991)

The Upset: Boyz II Men
“Walking in Memphis” is a pretty great song for being very adult contemporary 1992. But Boyz II Men went on to have six Top 10 hits in the next five years, starting with “End of the Road.” Marc Cohn well, he just seems like a really sweet guy.

The Winner: Paula Cole (1998)

The Upset: Fiona Apple
“I Don’t Want to Wait” is so inextricably linked to Dawson’s Creek that it’s used to make fun of Joshua Jackson in Urban Legends. Fiona Apple, meanwhile, has been making criticaly-lauded and adored albums for nearly two decades.

The Winner: Shelby Lynne (2001)

The Upset: Brad Paisley
Nothing against Shelby Lynne, who’s had an incredible story and was hardly – thirteen years and six albums into her career – a “new artist” when she won her Grammy. But Brad Paisley currently holds the record for most consecutive singles – 10 – that have reached number one on the Billboard Hot Country Songs chart.

The Winner: Maroon 5 (2005)

The Upset: Kanye West
Adam Levine‘s celebrity notwithstanding, we think it’s pretty safe to say that Kanye West may have been slightly more deserving of this award. To wit: Someone in the office asked in all seriousness if Maroon 5 was still together when we were discussing this piece. They are. They put out an album in September. Go ahead, name a song from it. We’ll wait.

The Winner: Amy Winehouse (2008)

The Upset: Taylor Swift
There was no way to predict Amy Winehouse’s tragic downfall in 2008; she looked like she had a massive career ahead of her. But Swift is currently the only artist to have had an album go platinum in 2014 – and maybe the last artist ever to have that happen – and while hindsight is definitely 20/20, this one still seems like an oversight. (Heartbreaking, yet still an oversight, with all due respect to Winehouse.)

The Winner: Esperanza Spalding (2011)

The Upset: Drake
Esperanza Spalding is an enormously talented bassist, vocalist and composer – watch her move Sting to tears in the above video. But three years later, if you mention her name to, well, anyone, it’s unlikely they’ll recognize it with the same quickness they would Drake’s.

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