Who was the first rapper to win the Grammy Award for Best Rap Performance?

DJ Jazzy Jeff & the Fresh Prince were the first winners of the Grammy Award for Best Rap Performance.

They won at the 31st Annual Grammy Awards in 1989 for “Parents Just Don’t Understand.” The duo consisted of DJ Jazzy Jeff, whose real name is Jeffrey Townes, and the rapper later known as actor Will Smith. Their winning song came from the album He’s the DJ, I’m the Rapper.

The award marked a major institutional recognition of hip-hop, which had developed from New York City block-party culture into a commercially powerful genre during the 1970s and 1980s. Rap categories were still new in the Grammy system.

The duo famously boycotted the ceremony because the new rap category was not included in the televised broadcast. Their win is therefore historically important even though viewers did not see the presentation during the main telecast.