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Michael ’Zebra’ Bailey: Art Outside The Institute

Street artist Michael “Zebra” Bailey creates and sells his charcoal portraits outside the Art Institute and on State Street in Chicago.

By Arts & Culture

  • Some of Bailey's portraits for sale on Michigan Avenue. (Photo: Juan Carlos Herrera.)
  • "Zebra" at work. (Photo: Juan Carlos Herrera.)
  • "Zebra" and a work in progress. (Photo: Juan Carlos Herrera.)

The northwest corner of Adams and Michigan is arguably one of Chicago’s busiest, thanks to its proximity to a certain well-known art museum just across the street. Each day, throngs of tourists, students, and workers squeeze past each other and, if Michael Bailey is drawing, sidestep an artist at work.

“I’ve been drawing since I was a kid,” said Bailey one steamy weekday afternoon. “I can draw everything, but portraits are what I like to do.” 

The Chicago native signs all of his works “Zebra,” and prefers to be addressed as such. According to his website, he chose the nickname to, “represent [his] black and white heritage.”

The name suits the artist’s chosen medium as well: The portraits Zebra draws (and the prints he makes from them for sale on the street) are rendered exclusively in dark charcoal on white cardstock. The high-contrast pieces of famous faces are perfect for catching the notice of passersby.

“I do a lot of musicians and rappers,” he said. “I do some comedians, too.”

If he’s interested in the subject, Zebra says, he’ll draw it. The subjects in most of the pieces he’s offered lately at the Adams and Michigan spot have been celebrities such as Beyonce, Kanye, and Madonna. However, Zebra’s online gallery shows hundreds more pieces separated into categories: sports, comics, and historical figures.

Zebra didn’t always sell art on the street. As he tells it, his path to his current gig has been “a rollercoaster.”

“I was an architect before,” he said. “That’s what I got my degree in.” After obtaining his B.A. in Architecture from the Illinois Institute of Technology (IIT), Zebra says he continued his education at the University of Chicago, acquiring an MBA. He moved to Atlanta and went into business for himself and, at least for a while, things went well.

“I was running a business, then I was doing art publishing and distribution,” he says. “I built up a million dollar corporation down in Georgia. I was a millionaire, then I gave it all away, threw it all away. I went to prison and got homeless. I didn’t like all that money. But I need the money now, I wish I wouldn’t have blew it all.”

With a laugh, Zebra said, “I went from poor and in the ghetto to architect, got the MBA, was a businessman, millionaire, top of the world, then back to the bottom. I wouldn’t be doing it if I hadn’t lost everything. But I’m doing what I love to do.”

If you’re looking for Zebra, try a couple blocks over on State Street, where he typically sets up shop. Drawings are three dollars apiece, and he does take commissions.

One Response to Michael ’Zebra’ Bailey: Art Outside The Institute

  1. Herb says:

    I just met the man in south central L.A.! Wow….amazing. he gave me a couple of Kobe prints with GiGi he had ..i gave him a few bucks. Raw talent. Praying for him to get back up.

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