When: Late '80s
Moment: Jerry Rice and teammates made their rap debuts in the "Team of the Eighties" music video.
Complex says: Jerry was known to get the better of Prime Time whenever the two played against each other. Yet, judging by Rice's lack of charisma in this clip versus the astronomical amounts of swag exhibited in Deion's "Must Be the Money" video, we're putting our money on Sanders in a rap battle.