The gold-selling single, produced by Jazzy Jeff, is from the duo’s multi-platinum-selling sophomore album, He’s the DJ, I’m the Rapper. “Parents Just Don’t Understand” is often credited with introducing rap music to the young set, as the song’s playful lyrics and lighthearted music video offer a different perspective of hip-hop culture. It won a Grammy for best rap performance and reached #112 on the Billboard Hot 100 and #10 on the R&B chart.

When asked about bridging the gap between hip-hop and celebrity status, DJ Jazzy Jeff credited “Parents Just Don’t Understand” as the starting point:

You don’t feel it when you’re doing it. Will [Smith] pretty much got into television because someone looked at the ‘Parents Don’t Understand’ video and realized that he could act. People who can act can sense when someone can act. If I’m a musician or a producer, I know when someone is good even when the rest of the world doesn’t know — I think that’s basically what happened. It wasn’t so much of a transformation; they want me to do this and it just happened to become incredibly huge. We’re used to being on stage in front of 30,000 people, so [with] 100 people, it was easy.