The Fresh Prince is Will Smith. This was his first American hit as a rapper, and it came at a time when he and Jazzy Jeff (Jeff Townes) were doing lots of comical songs to appeal to a younger crowd - their first single was "Girls Ain't Nothing But Trouble." Rap music had entered the mainstream by 1988, but just barely. DJ Jazzy Jeff & The Fresh Prince filled a niche for radio-friendly, relatable songs that were easy to understand. Unlike Run-D.M.C., LL Cool J, Big Daddy Kane and most other rappers at the time, Smith rhymed in a slow, controlled style and used simple words. DJ Jazzy Jeff did have a great deal of credibility, as he was known for his production skills and innovative scratching techniques.
In this song, Smith takes the character of a 16-year-old boy with parents who tend to beat him when he doesn't behave. Apparently, he's from a wealthy family as he takes their Porche for a joyride and gets pulled over and arrested for driving without a license. Smith was 19 when this was released, and his ability to take on a younger persona would serve him well when he began acting, as his first role was a high-school student in the TV series The Fresh Prince Of Bel-Air.
This won the first ever Grammy award for Best Rap Performance. The award was given out for one more year before it was divided into "Best Solo" and "Best Duo or Group" categories. The other winner was Young MC for "Bust A Move." Grammy voters clearly favored non-threatening performers in this category as well as the Best Hard Rock/Metal Performance category, which was given out for the first and only time in 1989 and awarded to Jethro Tull.
The video did very well on MTV and convinced NBC to greenlight The Fresh Prince Of Bel-Air. Directed by Scott Kalvert, it used the same look he created on the "Girls Ain't Nothing But Trouble" video, which he also used when he was hired to do the opening theme to The Fresh Prince Of Bel-Air.