How 88-Keys Went From Crate Digging To Collecting Polo Gear And Hanging With Kanye

I didn’t know 88-Keys until the day we met. Or I should say, I didn’t directly know him. He and I came from the same era; the same corner of the universe. We both grew up in the realm of misfits and renegades who would remake New York City in the mid-90s. My thing was skateboarding and Keys was in hip-hop and those two worlds first collided on the streets of Manhattan. Meaning, we had crossover friends aplenty and probably bobbed our heads at all the same shows.

The 88-Keys story is one you begin to recognize if you watch other episodes of my show, The Masters: a person with such certainty of purpose that rather than success seeming like a pleasant surprise borne out of a lucky break, it feels more like an iron-clad inevitability. The man knew what he was about at a young age and he followed it relentlessly. If he hadn’t met Q-Tip as a teenager, it would have been someone else. If he wasn’t producing for Talib Kweli and Mos Def, he would have had other rappers clamoring to rhyme over his beats.

Still… you’ve gotta envy his origin story.

“As I was making a beat one day,” 88-Keys said, “Q-Tip walks in with the Large Professor. Large Professor starts freestyling — as soon as he walks in the door — to my beat and he calls me 88-Keys in his freestyle. Right then, I thought ‘if I ever make it, that’s gonna be my name.'”

The rest, they say, is history.

Going into this interview, there were two things I needed to hear about. The first being 88-Keys famous friendship with Kanye West — which he shares the history of here (including the fact that 88-Keys pronounced the soon-to-be megastar’s name “cayenne”). The second? The massive Polo by Ralph Lauren collection that 88-Keys has been cultivating and wearing exclusively for more than a decade now. It’s a fascinating obsession to witness as Key brings us right inside his closet, where he keeps entire Polo lines, ordered by season.

Check the interview and stay tuned for more episodes of The Masters on Uproxx. If you’ve got a style icon from that era that you want to see me talk to, let us know in the comments!