Before Jay Z was the Jay we know today, he was just another unknown rapper struggling to get his big break. In the early ’90s, Jay hung with Big Daddy Kane and one day accompanied him to an episode of Rap City back in 1990. After host Prime and Kane talk about Kane’s new video, Prime asks Jay to spit a freestyle. It’s a crazy clip to see considering, well, what Jay’s done in the last 25 years. Watch it above.