Kris Kross – "Jump"

Year: 1992

Also in 1992, had I told you two kids who wear their clothes backwards and rap about jumping would end up with the No. 1 song in the country for eight weeks … well, if you were Jermaine Dupri you would have smiled wide, because he knew. Oh, he knew!

Vanilla Ice – "Ice Ice Baby"

Year: 1990

Back in 1990, well before the days of Eminem, the whole white rapper thing was more of a novelty than anything else. Sure, we had the Beastie Boys, but they were the exception to the rule. At the time they had already released Paul’s Boutique and were considered a true hip-hop act.

Whether it was fair or not, Vanilla Ice was viewed as a novelty. Sometimes, however, such as the case with the pet rock, and Beanie Babies, novelties blow up larger than anyone could’ve possibly imagined. “Ice Ice Baby” becoming the No. 1 song in the country was that moment for Vanilla Ice.