What song earned Will Smith his first Grammy Award?

The answer is: "Parents Just Don't Understand"

"Parents Just Don't Understand" won Will Smith and DJ Jazzy Jeff the first-ever Grammy Award for Best Rap Performance in 1989. The track dominated radio and MTV with a relatable tale of back-to-school shopping gone wrong.

But you won't find Smith or Jeff in any recordings of the ceremony. Russell Simmons organized a nominee boycott when the Recording Academy refused to televise the rap category. Other artists like Salt-N-Pepa and LL Cool J joined the protest, calling out the clear disrespect toward hip-hop as a genre.

While other rappers pushed boundaries, Smith and Jeff reached success in their own lane with clean lyrics and universal stories. That approach allowed "Parents Just Don't Understand" to cross over to mainstream audience who had never connected with hip-hop before. And boy did they connect, with the duo getting three more nominations (and one win) in as many years.

NBC executives spotted Smith's natural camera presence during his music video and interview appearances. Without any acting experience, his personality alone convinced the network to build a sitcom around him. "The Fresh Prince of Bel-Air" launched shortly after, transforming a Grammy-winning rapper into a television star.