Who was the first rapper to win a Grammy?

The broader hip-hop community and the organisers of the Grammy Awards, it seems fair to suggest, have not always seen eye to eye.

It took a while for the Grammys to even recognise hip-hop as a legitimate genre worthy of its own category, and, even after it did, there remained still a great deal of unhappiness between the two sides. It was so bad, in fact, that the first rap act to ever win an award at the ceremony refused to show up to collect it.

It was only in 1989, a whole decade after hip-hop had begun to be popularised by tracks like The Sugarhill Gang’s ‘Rapper’s Delight,’ that the Grammys decided the time was right for a standalone hip-hop category. The Best Rap Performance was introduced that year, but the award only remained in that particular form for two ceremonies.

It was split into separate solo and group categories from 1991 to 2012, when the two awards were combined into one again. If nothing else, this speaks to the general unease that the Grammys have tended to exhibit while attempting to handle hip-hop.

During that ceremony in ’89, when Best Rap Performance first appeared as a category, the nominees were DJ Jazzy Jeff & the Fresh Prince for their song ‘Parents Just Don’t Understand,’ Salt-n-Pepa for their classic track ‘Push It,’ LL Cool J for ‘Going Back to Cali,’ Kool Moe Dee for ‘Wild Wild West,’ and JJ Fad for ‘Supersonic.’ DJ Jazzy Jeff & the Fresh Prince were announced as the winners, making Will Smith the first rapper in history to win a Grammy for a hip-hop performance.

But there was a problem. DJ Jazzy Jeff & the Fresh Prince weren’t there to collect the award, and, had LL Cool J or Salt-n-Pepa won, they wouldn’t have been there to do so, either. That’s because those acts were all boycotting the ceremony, because they felt it wasn’t sufficiently respecting their style of music. 

Along with the introduction of a rap category that year, the Grammys also brought in an award for heavy metal. But, because of time constraints, the awarding of only one of these two gongs could be broadcast on TV. Which of them do you think was selected?

The rap category was relegated to the pre-televised section of the ceremony, much to the disgust of the hip-hop community at large. A boycott movement developed, with Salt-n-Pepa explaining the rationale for it quite concisely in a statement. “If they don’t want us,” they said, “we don’t want them.”

Another gripe from some elements of the hip-hop community related to the specific nominees that were selected. There was a feeling that these artists and their songs were not necessarily representative of what rap was doing around that time, with more interesting but less “acceptable” acts, such as Big Daddy Kane, KRS-One and NWA, all being overlooked.

The song that ultimately won the award, ‘Parents Just Don’t Understand,’ was by its nature very childish, with Smith rapping about how parents don’t get what life is like for teenagers. It’s quite mild-mannered.

The relationship between hip-hop and the Grammys has never truly been at ease since. The nature of the rap categories has changed a lot over the years, but plenty of deserving winners have consistently felt overlooked by the selecting committee. Rap is certainly broadly respected as art and as pop music these days, but, nonetheless, the Grammys can sometimes still feel like it’s behind the curve.