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Bay-B Jay-Z

Everything about this clip of Jay-Z on BET's Rap City screams 1990: the flattops, the pendant on a leather rope, the embarrassing AIDS talk, Jay's Where's Waldo shirt… not to mention his fresh 20-year-old face.

It's a cool moment to see in retrospect. Big Daddy Kane giving him the vouch was probably a big deal for Jay. And I'm willing to bet nobody in that room knew he would one day be part owner of a Brooklyn basketball team. Anybody want to bet?

Sources: MMM Vintage Videos