A Dreamer in a City of Many Dreams


“I’ve loved his music for a long time, so when I heard there was an exhibition of his art, I was shocked! I had to come check out this show,” an excited passerby exclaimed to me as I walked through the Matthew Rachman Gallery. The visitor, who introduced herself as a “huge fan of his punk rock,” explained that Willis has had a major impact on mental health awareness in the underground music scene. “He had schizophrenia, but he never gave up on his dreams," she said, adding, "I didn’t know he was an Artist!” She stared awestruck at the drawings in front of her.

“Wesley Willis: A City of Many Dreams” explores art and architecture through the eyes of a young man who dreamed of a Chicago with even more buildings. Exhibited at the Matthew Rachman Gallery in West Town, it is a celebration of a Chicago outsider artist and punk rock musician who spent his life documenting the city he called home. Never without his garbage bag full of work and supplies, plus a folding chair so he could set up and draw wherever he pleased, Wesley Willis hardly sounds like a Chicago cultural icon. But his work reveals a way of looking at the world in which architecture and art, imagination and theory, come together to produce a City of Many Dreams.

Most know Willis through his music—he has had various punk rock hits like “Rock & Roll McDonalds” and “Cut the Mullet.” However, he is also a celebrated artist, particularly popular overseas for his vibrant American cityscapes. Showcasing never-before-seen works from the private collection of architect T. Paul Young, this exhibition highlights Willis’s early work, which was drawn between 1981 and 1991.

Young, a long-time friend and collector of the artist who got his own start in Mies van der Rohe’s studio, has spent years trying to share Willis’s artistic talent with the world.

“I was in Chinatown in the early 1980s, and I saw a young man sitting and drawing. I immediately recognized in him a talent for architecture,” said Young. Young was then a professor at the Illinois Institute of Technology’s (IIT’s) College of Architecture, and he invited Willis to spend time at IIT's Crown Hall with his students.

“Being around the activity of Crown Hall gave him a new sense of self,” Young remarked. He gave Willis books to study and encouraged him to use ball-point pen and colored pencils to make his drawings last longer. He also helped Willis sell his drawings to students and faculty at IIT, introducing him to the idea that one could earn a living as an artist. “I wanted to share his talent with the students and convince him that his drawings were worth putting his name on.”

The show celebrates Young and Willis’s friendship and highlights how Willis’s exposure to architecture at IIT shaped his aesthetic and vision as an artist. While he never saw himself as an architect, Willis attempted to emulate the structure and look of architectural design. Many drawings feature black and blue pen on notebook paper, resembling blueprints. Many also take the form of a grid or blocks, featuring close-ups or different angles on buildings similar to those seen on maps or in architectural plans.

By far my favorite work of the show is The Chicago Cityscapes. A snapshot of various buildings and their inhabitants, this work speaks more than any other to Willis’s understanding of design and his perception of Chicago. Some blocks contain only scribbled windows, while others explore the sizes and shapes of different buildings as well as the relationship between buildings and the natural landscape. He also includes the vehicles and people that make up the city, illustrating how their movements and actions are dwarfed by the structures around them. (And we can’t forget the nod to his second love, music, in the bandstand at the bottom left corner.) The overall result is an almost abstract, yet still recognizable, interpretation of the city that reveals how architecture dominates Chicago’s landscape.


Wesley Willis, City of Many Dreams, 1991. Ballpoint pen and felt tip pen on cardboard, varnished and framed, 28 1/8 x 41 1/2 inches. © Wesley Willis. Images courtesy Matthew Rachman Gallery. Photo by Nathaniel Smith.


That said, there are certainly elements in his works that depart from architectural renderings and enter the realm of imagination. While depicting real city landscapes, Willis’s drawings are often brightly colored and scribbled scenes that appear almost child-like. The centerpiece of the show, City of Many Dreams, is a brilliant cacophony of colors and sites. Big cotton candy clouds command an etched blue sky, as bright green grass fans out against spiraled bushes.

In his art, Willis imagined himself as an architect who could help Chicago grow. “He saw Chicago as a City of Dreams, and his dream was to add more buildings to it. He even designed his own buildings in the Loop,” Young noted. “They don’t exist in real life, of course, but you can find them in some of his drawings.” Willis’s art was not only a way of documenting what he saw, but also a vehicle for exploring Chicago’s architectural potential.

In addition to illustrating Willis’s ideas for the city, his drawings offer a new perspective on Chicago’s classic structures. Thought to be his earliest drawing, Untitled (November, 1981) is a highly accurate rendering of the Loop, drawn on found cardboard with torn and browned edges. But while this piece is made from very simple materials, it reveals a sophisticated technical understanding of both architectural design and Chicago’s city planning. Reminiscent of blueprints, this work is a grid in a blue ink color scheme like those used by architects. Drawn from life with unforgiving pen, not a single line is out of place. This work is a remarkable feat of patience and perception.

Despite the precision and accuracy of the building outlines, Willis has left the architecture completely blank. Instead, he focuses his attention on the cars and people in the street below. His trucks are incredibly intricate, and it is only upon very close study that one realizes the streets are filled with hundreds, even thousands, of carefully drawn people. This reversal of architectural focus is a fascinating twist, and one which is explored throughout his drawings. In fact, while the buildings appear to be the central feature of these architectural drawings, it is often the vehicles and individuals in which Willis instills the most realism and movement.

“He loved the movement of the city, the activity of people and transportation,” noted Young.


Above: Wesley Willis, Untitled (November, 1981) – Detail

Below: Wesley Willis, Untitled (November, 1981) – Detail (including the Chicago Picasso sculpture in Daley Plaza ). Both images courtesy Matthew Rachman Gallery. Photos by Nathaniel Smith.



Despite his love of architecture, vehicles seem to be the things that Willis focused on the most. Hung between his larger landscapes are various small studies of trucks and vehicles, drawn in ballpoint pen on lined sheets of ordinary notebook paper. Remarkably precise, these miniature works are a sharp contrast to the scribbled and sketched landscapes that dominate the gallery.

Wesley Willis’s fascination with transportation is shared by his brother Ricky Willis, an architectural historian and artist with Project Onward. Ricky has spent his life exploring Chicago’s architecture, just as his brother did. Shaping cars and water towers out of materials he finds around the city, Ricky creates sculptural models of the same structures and vehicles that fascinated his older brother. Situated amid Wesley’s drawings, Ricky’s sculptures provide a moving counterpoint within this show, bringing Wesley’s drawings off the page and into a poignant 3D reality.

“I was never a teacher or a mentor to Wesley... I was just someone who could affirm that he was doing something worth doing,” Young explained. “But I can make sure his work is out there and not forgotten, because that’s been the whole point, from the beginning. To get him out there, in special places and special situations. He inspires people.”

Through Young’s efforts, Willis’s artwork has been shown across the world, in Switzerland, Germany, Belgium and Africa, and is in many major museum collections. And now, Young believes, Chicago is ready for him: “There’s been a change in the last few years, and this country is starting to recognize the importance of outsider art. Wesley is an important figure in Chicago’s cultural history.”

A patchwork of different Chicago architectural features, Willis’s unique drawings reveal the vibrancy of the city through bright colors, sharp lines and scenes of everyday city life. And while he may never have intended to be an artist or expected that his work would one day adorn the walls of a gallery, Willis had an impulsive need to create. “He had a vision of the city," said Young. "I think he just needed to get these ideas out of his system and onto paper."


Emelia Lehmann


“Wesley Willis: City of Many Dreams” is on display at the Matthew Rachman Gallery until November 17, 2019.


Emelia Lehmann is a recent graduate of the University of Chicago and an aspiring arts professional. An avid writer and researcher, she loves exploring the incredible arts and cultural opportunities in Chicago.

Wesley Willis, The Chicago Cityscapes, 1984. Ballpoint pen and felt tip pen on cardboard, 22 x 26 inches. © Wesley Willis. Images courtesy Matthew Rachman Gallery. Photo by Nathaniel Smith.

Wesley Willis, Untitled (November, 1981). Ballpoint pen and pencil on cardboard, 28 1/8 x 43 1/8 inches. © Wesley Willis. Images courtesy Matthew Rachman Gallery. Photo by Nathaniel Smith.

Wesley Willis, Untitled, 1982-1983. Ballpoint pen on lined paper, 8 ½ x 13”. © Wesley Willis. Images courtesy Matthew Rachman Gallery. Photo by Nathaniel Smith.



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