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.
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What was your process with this illustration?
The seed was planted once I knew the cover was celebrating Complex’s 20th anniversary along with Kanye, which is so perfect because Complex has done many stories on Kanye through the years, especially when he first started out. From there, it was figuring out how to say it all. So in my thinking about all the elements and not being too caught up in the past, I thought about the house and his fashion right now. We can put his past looks and merch on the bears and they’ll represent him now. I think the house was the first element and then my thinking about him sitting on the porch and then that made me think about it as if it was his throne. That opened the Akira idea and then everything just snowballed.
What about this Steve Jobs image?
You’ll notice how with the Apple computer references and the picture of Steve Jobs with the second-model Macintosh. But here you have Kanye’s Stem Player. And in the original picture with Steve Jobs, the screen read “hello,” but our Kanye computer screen reads “yellow,” playing off of “Ye.”
Why did you decide to include the Denim Tears jeans?
I just wanted to make it as current and up-to-date with where he is creatively and fashion-wise.
I did want to talk about why you decided to include his mother Donda as an angel.
Definitely the power of mother. We’re really witnessing the real power of Donda. Coodie and Chike then showed it to us in their documentary. She’s still the backbone; in the drawing, she’s his Tinker Bell. The Donda angel is always over his shoulder. She’s always there.
Can we talk a little bit about Chicago? Because I think one of the reasons why I really wanted to work with you on this cover is because there’s this inherent knowing and connection that you have with Kanye coming from Chicago and wanting to be creative and having your particular interests. And obviously, that inspired Kanye in some way. What is it about Chicago that breeds so much creativity?
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. 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. Virgil and I would have conversations about trying to do something with the youth in Chicago and letting them know that you don’t have to subscribe to that.
And Chicago has such a love for hip-hop culture because hip-hop is not originally from there. I just remember having friends of friends in New York and being in awe of the idea of rap music being on the radio. New York is just so hip-hop, especially in the ’90s. It’s like air in New York. But in Chicago, it’s gang culture. I was there when gangbangers didn’t even listen to rap music. So my friends and I starved for it more being from Chicago.
