The 1989 first Grammy Award for Best Rap Performance went to which duo for "Parents Just Don't Understand"?

DJ Jazzy Jeff & the Fresh Prince won the first Grammy Award for Best Rap Performance for “Parents Just Don't Understand.”

The award was presented at the 31st Grammy Awards in 1989, making the duo the inaugural winner in the category. DJ Jazzy Jeff was Jeffrey Townes, while the Fresh Prince was Will Smith. The winning song appeared on their 1988 album He's the DJ, I'm the Rapper and turned a comic story about teenage frustration and parental rules into a mainstream rap hit.

The victory was historically important but controversial. Rap and heavy-metal categories were introduced that year, yet the rap award was not televised because of time constraints. Jeff and Smith joined a boycott led by several nominees, including LL Cool J and Salt-n-Pepa, who objected to the Academy's treatment of rap. Jeff attended the presentation at Los Angeles's Shrine Auditorium, while Smith was absent. Another common mix-up is confusing this award with the later Best Rap Solo Performance category: the original category was discontinued after 1990, then rap categories were reorganized and eventually recombined in 2012.