The Dan Ryan Expressway at 33rd Street, 1986 Credit: Wesley Willis

Last summer, Intuit began exhibiting nearly a dozen Wesley Willis drawings as part of “Chicago Calling: Art Against the Flow” in conjunction with Art Design Chicago, an expansive, yearlong celebration of the city’s art history. Intuit’s show honored Willis and nine other local outsider artists (including Henry Darger, Lee Godie, and Mr. Imagination), and argued for their place in the historical canon. Willis, a six-foot-five schizophrenic Black man who drew detailed renderings of Chicago’s skyline and infrastructure, was the youngest figure included in the show—he was just 40 years old when he died in 2003—and he transcended the art world like none of the others.

In the 80s, Willis earned a reputation as a street artist. He sometimes worked on large pieces of poster board on the sidewalks and CTA platforms where he also sold his artwork. By the 90s, he turned his attention toward music, and his repetitive, diaristic Casio-keyboard ditties brought him unparalleled levels of fame; in 1995, he landed a deal with Rick Rubin’s major-label imprint American Recordings. Willis also independently released more than three dozen albums, and storied San Francisco punk label Alternative Tentacles repackaged many of those songs on three Greatest Hits compilations. Willis never stopped drawing, either; he once told insanely comprehensive interviewer Nardwuar that he’d made 40,000 drawings.

Willis sold his pieces for as little as $20, though he was happy to bargain. He exchanged at least one drawing with former Quenchers bar owner Earle Johnson for a turkey sandwich and a glass of orange juice. Since Willis died in 2003, the cost of his art has skyrocketed; in July, Humboldt Park vintage shop An Orange Moon held a sale for eight Willis pieces, and half the drawings were priced at $1,800. His art has found its way into the collections at Intuit, the MCA, and the Art Institute, but the majority of Willis’s drawings remain in the hands of collectors or those he sold to directly. Few have bought as many of those drawings as T. Paul Young, an architect who became a patron of and mentor to Willis after a chance meeting in November 1981. Young archived several hundred pieces of Willis’s over the years, and he supplied about 60 to the Matthew Rachman Gallery for “Wesley Willis: City of Many Dreams,” which opened on September 13.

Young met Rachman this past winter, when a mutual friend suggested Young could help with a springtime exhibit dedicated to architect Mies van der Rohe. At age 17, Young got a job at Mies’s Chicago firm, and his spiritual relationship to the modernist master runs deep. Young now serves as the executive director for the Bauhaus Chicago Foundation, which preserves the legacy and work of the New Bauhaus, a local offshoot of the influential German art school; Mies was the last director of the original architectural incubator. Needless to say, Young had material for Rachman. “That’s when I discovered Wesley’s connection to Paul, and all the works,” Rachman says.

Young has showcased some of his Willis art before—he provided 30 drawings for a 2008 gallery show at suburban Dominican University. “For a long time, I’ve been working toward promoting Wesley’s legacy in various ways,” Young says. He even wrote a book, tentatively titled The Early Work of Wesley Willis, though the project never advanced beyond the draft phase. Through the decades, Young built a substantial archive of Willis-related ephemera—sketches, unfinished drawings, and photos, in addition to the completed works. Though he’s sold some pieces from his collection, Young felt the timing was right to mount a proper exhibit of Willis’s work.

“Paul and I spoke about it and agreed that Wesley deserved a show of all his work, and not just have this stuff be sold off,” Rachman says. “We wanted to honor him and his relationship with Paul, and tell that story.”

Detail of the Dan Ryan Expressway, 1984Credit: Wesley Willis

Young unspools some of his long history with Willis in an essay for the “City of Many Dreams” catalog. Art brought the two together. Young was teaching at the Illinois Institute of Technology when he noticed then 18-year-old Willis selling a large drawing of Daley Plaza in Chinatown. Young was taken by the young man’s talent and invited Willis to sit in on his first-year architecture classes. Willis became ensconced at IIT without ever enrolling, spending roughly four years in the 80s sitting in on classes and hanging out in Mies’s iconic S.R. Crown Hall building.

The body of work in “City of Many Dreams” focuses on Willis’s material from the 80s, and demonstrates the artist’s architectural foundation. Throughout his career, Willis rendered urban vistas in pen and marker on large slabs of poster board, and though he always had an eye for details, many of these pieces display his most painstakingly granular labor. In an aerial picture of Streeterville, Willis demarcated every building’s story, and if you focus on his depiction of Lake Shore Drive, you can also make out impossibly teeny vehicles. In his essay, Young notes Willis’s attention to architectural specificity—he’d draw mullions, the vertical structures that divide up windows, even if the buildings he drew didn’t contain any in real life.

The show also crucially captures Willis’s process through the miscellaneous scraps Young held on to for decades. There are crayon portraits of Young’s suburban house, small illustrations of buildings on photocopies of photographed cityscapes, and rigidly crafted commercial trucks drawn on canvases including ruled paper, a torn sheet, and what appears to be the back of a fragment of wrapping paper.

Young cataloged all his Willis works by dividing them into thematic categories, to each of which he assigned a number, one through ten. Drawings and sketches, for example, were the first category; and each item received its own number within the category. Young wrote Willis’s initials and these two numbers on the back of each piece in pencil.

The show’s crown jewel is the Daley Plaza illustration Young bought from Willis when they first met. It’s the earliest known Willis drawing in existence. In the context of the other pieces in Young’s collection, this piece underscores Willis’s artistic growth. He was detailed but selective; he drew brand names on trucks, but did not depict the Daley Center’s skeletal steel surface. Nearly every other building is also blank, but Willis drew vehicles in a few of them.

Willis’s approach advanced as Young became his mentor and biggest champion. According to Young, Willis wanted to be an architect, which shouldn’t come as a surprise considering the care he took illustrating Chicago’s skyline. He loved buildings—in fact, Young says Willis wished Chicago had even more towers crowding downtown. “He thought Chicago should be more like New York,” Young says. “He loved the thickness of the city.”  v