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“Drape it in color”: Wesley Willis’ Chicago comes to MMoCA

The museum’s collection now includes seven drawings from the Chicago visual artist and musician.

Image above: Wesley Willis, “Dan Ryan Expressway Past 51st Toward 47th St.,” 1994. Images courtesy of Madison Museum of Contemporary Art.

Wesley Willis created an enduring, open-hearted, and lovably outrageous body of music before he died in 2003 at the age of 40. But well before he fired up some chintzy pre-programmed keyboard patterns and declaimed about his struggles with mental illness, commanded us to “Suck A Cheetah’s Dick,” or sang the praises of the great death-metal band Bolt Thrower, Willis built a reputation for drawing his hometown of Chicago. During the ’80s and ’90s, he’d tote his art supplies to street corners around the city and chat up passerby, making new friends and selling his work to them for $10 or $20 a piece. 

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A sponsor display for The Sessions at McPike Park.

Willis’ music and charismatic presence—he was an imposing, 6′ 5″ man who frequently sported a bruise on his forehead from his habit of greeting people with a friendly head-butt—has overshadowed his visual art in the broader pop-culture consciousness. But some collectors and curators in the art world have worked on fixing that, including here in Madison. The Madison Museum of Contemporary Art added seven of Willis’ drawings to its permanent collection in December, and three of them are now on display in the lobby, available to view during MMoCA’s currently limited hours. The ones you can see now—”Dan Ryan Expressway Past 51st Toward 47th St.,” “51st Street, Wentworth, Wells,” and “Michigan Avenue”—were drawn between 1989 and 1994.

Willis rendered his hometown in densely thatched lines of felt-tipped market and ballpoint pen. He gives his viewers a sharp compositional sense of Chicago’s skyline and plenty of other buildings and landmarks, from Buckingham Fountain in Grant Park to a 51st Street McDonald’s to the Mies van der Rohe-designed Crown Hall on the Illinois Institute of Technology campus. 

Willis was interested in architecture throughout his life, and sat in on architecture classes at IIT after befriending a student there, as the Chicago Reader‘s Leor Galil explained in a 2019 story. Willis rarely makes a full departure from reality, but his color choices turn the steel and glass and concrete of the city into something friendlier, more ripe with possibility. You might also notice the occasional made-up futuristic car or an imagined building inserted among the real ones. Willis explained in a 1988 local TV documentary called Wesley Willis: Artist Of The Streets that he first drew a scene in pen, then used markers to “drape it in color.”

Of the works on display now, “Dan Ryan Expressway Past 51st Toward 47th St.” (see it at the top of this story) might be the standout. Willis drew the Dan Ryan Expressway a lot. It’s hardly among the more iconic or appealing sights in Chicago, and Willis’ experiences with it might not have always been good ones—he sometimes experienced hallucinations while traveling the city on buses and the CTA Red Line trains that run down the expressway’s center on the South Side, what he called his “hell rides.” But Willis’s orange road, blue-green barriers, and sharply rendered buses alongside the occasional three-level car make the expressway teem with joy and warmth.


“Michigan Avenue,” 1989.

“Michigan Avenue,” 1989.

“The compositions themselves, the patterns that a marker can make, the lines that are generated throughout the composition, are just mesmerizing and captivating,” says Mel Becker Solomon, MMoCA’s Curator of the Collection. “They teeter on the edge of architectural drawing, because Willis was interested in becoming an architecture student.”

Jeff Ginsberg, a retired Columbia College Chicago theater professor, gifted the seven works to the museum in honor of his late partner Hal Brun, who had a long career in special education but also amassed a sizable art collection. Becker Solomon found her way to Ginsberg through a friend who hoped Chicago’s bigger art institutions wouldn’t snap up everything in the Brun collection. Willis’ stock is rising in the art world—partly the classic bitter story of artists never getting their due while they’re alive, and partly the impact of the traditional art world getting more comfortable with so-called “outsider” or “self-taught” artists.

When visiting Ginsberg last year, Becker Solomon recognized a lot of the work in the collection, including a painting from Wisconsin’s own Fred Stonehouse. At one point, Ginsberg reluctantly pulled out a portfolio from under a bed, not sure whether Mel would be interested in the contents. “I gasped, because they’re the Wesley Willis drawings on posterboard,” Becker Solomon recalls. There were eight in total; Ginsberg kept one and donated the rest, Becker Solomon says.

Wesley Willis fits right in with two themes Becker Solomon has emphasized when putting together shows and acquiring works at MMoCA. One, the museum has a lot of work from Chicago-based artists in its collection, and has featured the works of the 1960s Chicago Imagists movement in two recent shows. Two, Becker Solomon notes that MMoCA also collects a lot of “outsider” art, including pieces from Simon Sparrow and “Prophet” William J. Blackmon

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The term “outsider art” can be slippery, and Becker Solomon prefers the term “self-taught,” but the curator sums it up as “artists who have this creative output but are not necessarily associated with an institution or a dealer or a gallery or even have professional art training. They just have these works of art that have this immense expressive power that are not driven by the marketplace or trying to get into a museum or gallery representation.”


“Crown Hall - 3360 S. State Street,” 1989

“Crown Hall – 3360 S. State Street,” 1989

Willis was a poor Black man who suffered from schizophrenia and never amassed wealth from his own work, but his work is definitely making money for other people now. It’s strange bordering on obscene that you can get your hands on a Wesley Willis drawing through Christie’s. Becker Solomon hopes this backwards equation of value will change for artists living and working now: “Thankfully, there’s pressure on gallerists and the museum world to rightfully pay those artists who are working,” Becker Solomon says. MMoCA felt some of that pressure directly in December, when more than 200 artists signed an open letter protesting some of the museum’s business practices, leading to some changes.

It helps that these works were a gift, and belong to a museum that is free to visit. It also seems that Brun got the drawings right from the source. Brun met Willis when Brun was in downtown Chicago volunteering as a docent at the Museum of Contemporary Art Chicago. “[Hal] would just start conversations, or Wesley would start conversations with him… he would see Wesley drawing and buy a work for $20 or $30,” Becker Solomon says.

Willis’ spartan, on-the-go style of working makes the intricacy and character of the drawings even more impressive. “He’s working on his knee, on a stack of posterboards, on a sidewalk in a folded chair,” Becker Solomon says. “I mean, he’s using one of his ballpoint pens as a ruler to make his straight lines.” 


“Buckingham Fountain,” 1992

“Buckingham Fountain,” 1992

Becker Solomon initially wanted to display the Willis works in March. As MMoCA figured out its pandemic re-opening strategy, the plan changed to including all seven of the works in a “road trip”-type exhibition showcasing the American landscape. That plan has also been put aside, but Becker Solomon does hope to show more of the works in future exhibitions drawing on the permanent collection. “I’m hoping to shift programming to have artists in conversation with artists in the collection, so I would really love to see an artist working with Wesley Willis’ work or responding to something else in the collection that creates a dialog between that work and their work,” Becker Solomon says.

This art succeeds in showing us a very different side of Wesley Willis—analytical, obsessed with capturing his daily surroundings in detail, but still playful. 

“I know when he came into the collection a lot of people were like, ‘Oh, my gosh, Wesley Willis! I remember going to a concert or getting a head-butt from him,'” Becker Solomon says. “But I really wanted his artwork to be front-and-center in the museum.”

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