80's Guilt #46: DJ Jazzy Jeff & The Fresh Prince “I Think I Can Beat Mike Tyson” (1989)

In case anyone hasn't yet noticed, this list has so far been enormously heavy on the summer of 1989. We have no idea whether this will continue throughout the entire list, but the magic of this particular year can not be underestimated. When people think of amazingly corny and awesome 80's nostalgia, the last two years of the 80's (and 1990) should really be the focus, in our opinion...

So once again, for those who remember 1989, Mike Tyson was a huge fucking deal, and all the kids were like "holy shit, Mike Tyson." So it made sense for Will Smith and Jazzy Jeff to try cashing in on the hype with some more of their made-for-children novelty rap. At the time, Will was clearly a huge fan of Rakim, which helps to guide his rap flow tremendously. If you watch closely, Carlton from Fresh Prince and Don King make some friendly cameos in the video...

Also, look out for an unexpected moment of genius when Will Smith ends a line with the word "thing," and then instead of rhyming the next line with "ring" there's the sound of a bell from a boxing ring.