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.”
“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.
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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