I originally wanted to shoot Kanye for the cover. This was the big splash/introduction I was trying to make with my first cover as Editorial Creative Director at Complex. I also thought a Kanye cover for Complex’s 20th anniversary issue made perfect sense. We hadn’t had a cover of Kanye in a while and a short story showing Ye’s latest iteration was needed. I worked hard to make this happen – it didn’t – but before I knew it wasn’t going to happen, I realized we would need a plan B. Reggieknow to me immediately came to mind.

If you don’t know who Reggieknow is, go read this detailed profile that Lei Takanashi wrote about him a few years ago. But Reggieknow walked so many Chicago creatives could run. He helped cultivate a hip-hop scene in Chicago in the 90s with Dem Dare parties and later worked in advertising for Burrell, the black-owned, Chicago-based ad agency. You’ve probably seen a few of his “Obey Your Thirst” Sprite commercials featuring the likes of Kobe Bryant, Pete Rock, Eve, and Mos Def.

I remember the first time I saw his Dem Dare flyers. I thought they were works of art. The flyers were black and white, but still very dynamic. The people he illustrated looked so cool, so black, and they were so well dressed. He put them in the finest Polo pieces – Reggieknow was an avid Polo collector who helped build that community in Chicago, which influenced Kanye’s early fascination with the brand – as well as four-finger rings, Columbia ski goggles, Timberland boots and North Face jackets. . And the hair ?!? He’s paid so much attention to showcasing just how diverse black hair is, whether it’s locs, bowl cuts, or mini afros accessorized with a bobby pin. He was someone who wanted to see himself in the art he created.

In many ways, this connects to Kanye, who continues to reveal himself in his art and remains committed to a look. Reggieknow and Kanye are friends – Kanye once described seeing him in Chicago and being amazed by his outfit. They also both went to the Art Academy of Chicago (at different times). They have very different professional backgrounds, but they are both artists from Chicago who have had to challenge the boundaries created for them to succeed and build their own world.

“What I realized as I got older is that Chicago is a working-class city. It’s in the middle. And so the influences came from the east coast and the west when it came to hip-hop culture. I learned later that the goal was to keep the city as consumers,” says Reggieknow. “You cannot create. We just need you to consume. And so I think the box that they tried to keep us in created kind of a push. The city is also so segregated. It’s so working against you there.

I could say a lot about the cover, but I’ll let Reggieknow explain what happened in his thoughtful illustration of Kanye for Complex’s 20th anniversary issue. It was an honor to work with him and hear firsthand how he thinks and creates. Enjoy. Dig into references. And go build the world you want to be a part of, even if it’s as simple as wearing a fly outfit that makes you feel like you’re your full self.