It’s hard to imagine now, but there was a time when rap didn’t have a category at the Grammys.
That changed on Feb. 22, 1989, when DJ Jazzy Jeff & The Fresh Prince—Jeffrey Townes and Will Smith—won the first-ever Grammy Award for Best Rap Performance for “Parents Just Don’t Understand.”
The track, from their 1988 album He’s the DJ, I’m the Rapper, had already crossed into the mainstream, peaking at No. 12 on the Billboard Hot 100 and earning Gold certification. But its Grammy win marked something bigger than chart success. It was the Recording Academy’s formal acknowledgment that hip-hop was no longer a novelty, it was a defining force in American music.
“Parents Just Don’t Understand” played like a three-minute sitcom. In the first verse, Smith recounts being humiliated on the first day of school after his mother buys him hopelessly uncool clothes. In the second, he borrows his parents’ Porsche without a license, tries to impress a girl and ends up arrested. It was funny, accessible and relatable—and it helped bring rap into suburban living rooms.
But the historic win came with controversy. The rap award was not presented during the televised broadcast, prompting DJ Jazzy Jeff & The Fresh Prince to boycott the ceremony. Fellow nominees LL Cool J and Salt-N-Pepa joined in protest. Salt-N-Pepa later issued a blunt statement: “If they don’t want us, we don’t want them.”
Even so, the category stuck. Within a few years, it expanded into multiple rap awards. Decades later, artists like Jay-Z, Kanye West and Kendrick Lamar would dominate the field. Lamar leads all nominees in the category with 12 nominations and eight wins.
But it started here—with a teenage anthem, a gold trophy and a genre demanding to be taken seriously.
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