Over his lengthy and celebrated career, Jay Z has become known for many things, including his flow: Oftentimes laid-back, and coming off with an air of nonchalance while remaining steadfastly deliberate.

He didn’t always sound that way, though.

Old tracks and freestyles have made that much clear, as double-time rapping was often Hov’s forte. He’s dabbled with that, at times, in the years since his mainstream breakthrough of the late ’90s, but it’s certainly not the sound that a casual fan is used to hearing from Jay.

Which is what makes this clip of him on BET’s “Rap City” alongside Big Daddy Kane, which we spotted at Miss Info, all the more glorious. It’s from 1990, and is reportedly his first appearance on TV.

In an interview with his own site, Life + Times, in 2011, Jay explained the evolution of his flow.

“When I first started writing raps, I was a kid,” he said. “I started when I was 9 years old, so I didn’t have real life experiences. The thing I drew off of was being creative. It was more about the technique than what I was saying. I was trying to say things in different ways — doing faster flows and triplet styles. I was exploring all that. It was more of a technical thing.”

“It became more about the words, more about what I was saying and more about this emotion and this truth. I still had the technical side because I was writing for so many years.”

“Don’t just judge us as ignorant kids or drug dealers,” he said. “It’s much more than that.”

If there was any doubt about that in 1990 years ago, he’s taken the last 25 years to indeed prove it’s much more than that.