I originally wanted to shoot Kanye for the cover. It was the big splash/introduction I was trying to make with my first cover as the editorial creative director at Complex. I also thought a Kanye cover for Complex’s 20-year issue made complete sense. We hadn’t had a Kanye cover in a while and a new one showing the latest iteration of Ye was necessary. I worked hard to make it happen—it didn’t—but before I knew it wasn’t going to happen, I understood we would need a plan B. Reggieknow immediately came to mind. 

If you don’t know who Reggieknow is, go read this thorough profile Lei Takanashi wrote on him a couple of years ago. But Reggieknow walked so a lot of Chicago creatives could run. He helped cultivate a hip-hop scene in Chicago during the ‘90s with Dem Dare parties and went on to work 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 people like 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 vibrant. The people he illustrated looked so cool, so Black, and they were so well dressed. He put them in the finest pieces from Polo—Reggieknow was an avid Polo collector who helped build that community in Chicago, which influenced Kanye’s early fascination with the brand—along with four finger rings, Columbia ski masks, Timberland boots, and North Face jackets. And the hair?!? He paid so much attention to showing how diverse Black hair is—whether it was locs, bowl cuts, or mini afros accessorized with a hair pick. This 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 friendly—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 career paths, but they are both artists from Chicago who had to defy the boundaries created for them in order to succeed—and build their own worlds. 

“What I’ve come to realize as I get older is that Chicago is a working town. It’s in the middle. And so the influences were coming from the East and West Coast as far as hip-hop culture goes. I learned later that the goal was to keep the city as consumers,” says Reggieknow. “You can’t create. We just need you guys to consume. And so I think that the box they tried to keep us in created a type of push. The city is also so segregated. It’s so much working against you there.”

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