Watch Jay Z's First-Ever Television Freestyle in 1990


BET’s Rap City in 1990 was a far cry from the beast it eventually became: before there were elaborate sets (aka your mom’s basement but graffiti’d), it was simply a room, crates, and a couple of seats. In this cozy setting, a babyfaced Jay Z made his first-ever TV appearance, flanked by Big Daddy Kane who gave the then-young rapper the cosign because he probably felt like he needed to.

If it needed any timestamps other than Jay’s tiny face: they talk about the time “before AIDS,” homie is wearing a giant necklace on a leather rope (not quite a leather Africa pendant; maybe a satchel of incense?), and Jay’s “funky freestyle” is rife with lines like “the time out, the riggity rhyme out.” Or, as YouTube commenter James Stephens put it “Alotta skiggidty and iggigitis but jay killed it the Goat besides Nas.” For more Jay Z skiggidty iggigitis, give this song a whirl:

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