So, you're wondering, how does this song make any credible list? Aside from the fact that Will Smith, a.k.a. The Fresh Prince, is actually a good story-telling rapper (don't deny it), this song made Grammy history by winning the first Grammy Award for Best Rap Performance in 1989.
But, the story doesn't end there. Will Smith and DJ Jazzy Jeff boycotted the awards because they were not allowed to publicly accept their award or be featured during the show's live airing. The pair instead attended a "boycott party" also attended by other prominent acts in Hip Hop at the time.
I think this song hit close to home for a lot of people because we had more than likely lived a version of it ourselves. Who didn't have one of their parents dress them in something that they did't want to wear when they were a child (read "Those courderoys make you look so handsome!"). Our do something dumb when our parents left us on our own.
Here is the video. Enjoy-
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