Rolling Out

Naughty By Nature over 2Pac? The worst Grammy wins of all time


It’s Grammy Awards time, and all of the world of music is planning to celebrate the industry’s biggest night. Artists and producers and execs will be waiting patiently to hear their names called and to receive their little golden Gramophones.

But in all of the hubbub, one important facet of the Grammy Awards’ history seems to get ignored: the fact that they get it wrong a lot.

Winning a Grammy is undoubtedly an honor. It’s a prestigious award. But the Grammy committee has shown themselves to be fairly clueless when it comes to contemporary music. And it’s been that way for decades.

The 1960s were largely musically defined by Motown and the British Invasion, but when you take a glance at the kind of music that won Album of the Year — there’s mostly middle-of-the-road tripe by artists like Stan Getz and Judy Garland. The 1980s featured some brilliant albums and songs, from new wave to hip-hop to punk and beyond. But most of what won Grammys was generic pop.

So, with that spirit of earned skepticism in mind, we decided to take a look at the 10 worst Grammy wins of all time. To be clear; this is not to say these are “bad” albums; just to say that there is no way they should’ve taken home the crown on music’s biggest night.

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