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The Artistic Rendering of Wesley Willis

by Aron Packer,
Senior Specialist,
Contemporary &
Outsider Art


In our Modern Design + Post-War & Contemporary Art auction on Thursday, February 25, 2021, Toomey & Co. will offer four Wesley Willis drawings. During the 1980s and 1990s, Willis was a fixture on Chicago’s Outsider art and underground music scene. Formerly beloved by just the alternative, bohemian set, Willis has lately become more widely appreciated by art and music fans alike.

Portrait of the Outsider Artist: Wesley Willis (May 31, 1963 – August 21, 2003)


Wesley Willis was a complex human being. He was diagnosed with schizophrenia in his late 20s, and had other maladies and tics, which all contributed to the great art and music he created over his too short life.

Artist/musician Wesley Willis. (Photo by and courtesy of Carla Winterbottom)

A true savant, Willis committed himself fully to art and possessed unusual, obsessive memorization skills with his song lyrics. While Willis would often draw all over Chicago en plein air, he had a kind of photographic memory and did not need to have his subject of choice in front of him.

Willis’ work is immediately recognizable. His signature drawings have an active and quick architectural rendering style. You really see visual movement in much of his work.

Wesley Willis works on a drawing at home. (Photo by and courtesy of Carla Winterbottom)

He employed various perspective devices, distorting his subjects and breaking drawing “rules” whenever and however he wanted. He created consistently compelling packed urban visuals across the artistic spectrum. Willis’ somber and peaceful urban scenes appear less busy upon closer inspection, with large breadths of clouds regularly dominating low horizon lines.

Life in the Fast Lane with Willis


Almost always working on Crescent board, Willis would take a section of the city of Chicago and render a large swath of his viewing angle. For example, one of his favorite vantage points was overlooking the Dan Ryan Expressway, which gave Willis a clear perspective of the downtown skyline and the ‘L’ train. From there, he drew scenes like: The Comiskey Park Old and New, 1993 and The Dan Ryan Expressway, Root St, 1990. 

Wesley Willis (American, 1963-2003)
The Comiskey Park Old and New, 1993, ballpoint pen and marker on Crescent board, 28″ x 40 1/2″
Toomey & Co. Auctioneers, Art & Design, March 8, 2020, Lot 35
Estimate $600-800
Sold for $1,375

Wesley Willis (American, 1963-2003)
The Dan Ryan Expressway, Root St, 1990, ballpoint pen and marker on Crescent board, 28″ x 40 3/4″
Toomey & Co. Auctioneers, Modern Design + Post-War & Contemporary Art, February 25, 2021, Lot 11
Estimate $600-800

Willis Maps Chicago’s Skyline 


Taken together, various titles of works by the quite prolific Willis constitute a veritable map of Chicago both geographically and culturally. In recent years, Toomey & Co. has been fortunate to play a part in expanding awareness of and demand for such Willis compositions as: The Shore Line, 1991Area Skyline of Chicago, circa 1996Monroe Wabash Madison (Chicago), 1993; and River City, 1986, which sold for $3,900 over its $600-800 estimate.

Wesley Willis (American, 1963-2003)
River City, 1986, ballpoint pen and marker on Crescent board, 28″ x 40″
Toomey & Co. Auctioneers, Art & Design, December 6, 2020, Lot 129
Estimate $600-800
Sold for $3,900

Two of the drawings in Modern Design + Post-War & Contemporary Art on February 25, 2021 very much capture the grand sweep of Chicago’s iconic cityscape: Skyline of Chicago, 1987 and Buckingham Fountain, 1990

Wesley Willis (American, 1963-2003)
Skyline of Chicago, 1987, ballpoint pen and marker on Crescent board, 28″ x 37″
Toomey & Co. Auctioneers, Modern Design + Post-War & Contemporary Art, February 25, 2021, Lot 10
Estimate $600-800

Wesley Willis (American, 1963-2003)
Buckingham Fountain, 1990, ballpoint pen and marker on Crescent board, 28″ x 41″
Toomey & Co. Auctioneers, Modern Design + Post-War & Contemporary Art, February 25, 2021, Lot 13
Estimate $600-800

Memories of Willis and Friends


My first sightings of Wesley were in the 1980s. I was going to Circle, which is now part of the University of Illinois at Chicago campus. I used to take the ‘L’ train’s Red Line to the Blue Line from East Rogers Park, transferring at Jackson and going down the tube to make it to my stop at Halsted.

Wesley Willis converses with fans after his concert/art show at famed music venue CBGB in New York City, 1996. (Photo by and courtesy of Carla Winterbottom, manager for the American Records/Juxtapoz tour)

I was always in a rush, but I remember hearing about a guy carrying a folding chair and poster board around and doing drawings of the city with ballpoint pen. I was getting interested in Outsider art, but I never really stopped when I saw Wesley at work. My wife recalls spotting him at many Red Line stops and how he looked youthful like a boy then. Early on, I started noticing that many friends had drawings by Wesley. Unfortunately, I did not get many at that point, just as I missed out on the works that Lee Godie sold directly around town. I suppose I felt that I could not always spare the $10 or $20 they wanted.

Fast forward to Wicker Park in the early 1990s. I had my Aron Packer Gallery space at North, Damen, and Milwaukee Avenues. It was on the second floor of the Flatiron Arts Building and I could see everything at the bustling six-corner intersection. I often would see Wesley hanging out at the Copy Max below me or in front of Earwax Café. He usually wanted me to get a drawing and mostly I could not, but sometimes I did. Sadly, I no longer have them, since they fell victim to a basement flood.

Wesley Willis at home with one of his drawings on the wall seated next to friend and roommate Carla Winterbottom, 1986. (Photo by David DiTroia and courtesy of Carla Winterbottom)

Whenever I crossed paths with Wesley, he would always want us to “head butt,” but in a gentle way, in which we simply connected our foreheads. It was sort of like a Star Trek-style mind meld, where we would psychically join our thoughts and feelings at that moment.

I finally had a show with Wesley in 1995. I do not remember exactly how it came about, whether I asked Wesley himself or his good friend and roommate Carla Winterbottom. We hung my space with several of Wesley’s drawings and had an opening reception for him. Carla knew him better than anyone. They had met at the Genesis Art Supply Store on Western Avenue where she worked. Here are some of Carla’s recollections:

“One thing that I just loved about Wesley, as a fellow artist, was seeing his sense of joy, dedication and discipline in making art. No matter the obstacle (and there were plenty), Wesley was undaunted, and kept his sense of humor. In fact, he absolutely loved to laugh at his own antics and wordplay. Double entendres, triple entendres, sound making, etc. Frankly, those were the biggest perks of being his roommate; we were in cahoots while those moments escalated to a pure childlike glee. True joyrides. The man knew happiness and it was infectious. He had a deep wisdom also, a sense of decency and a need to be a good citizen. All in all, he embodied the strangest, most wonderful combination of charm and chaos.” — Carla Winterbottom on Wesley Willis


Willis the Underground Musician and His Cult Following


Wesley Willis performs at his concert/art show at famed music venue CBGB in New York City, 1996. (Photo by and courtesy of Carla Winterbottom, manager for the American Records/Juxtapoz tour)

The wildest part of the reception was when Wesley played a jaunty, punk-inflected music set. We hosted that in the Around the Coyote office next door. This involved a Casio-style keyboard, which had all sorts of programs for rhythms and prerecorded arrangements. Wesley performed his lively yet edgy tunes one after another. His in-your-face album and song titles included: Torture Demon Hell Ride, “Sooby Dooby,” “I Whipped Batman’s Ass,” and many more graphic ones. Wesley also had songs about Christmas and featuring rock stars, celebrities, and so forth.

Wesley Willis takes a break from playing his keyboard at home to talk on the phone, 1992. (Photo courtesy of Carla Winterbottom)

To catch up on Wesley’s music career, visit Spotify or YouTube to see him in action solo, or check out his recordings and performances with his heavy metal band the Fiasco on Spotify or YouTube.

Far from being tangential to his drawing practice, Wesley’s music making complemented and interacted with his visual art in many cases. Wesley’s most streamed song on Spotify is “Rock N Rock McDonalds,” which has 1,674,312 plays (as of February 5, 2021). While many of his songs explored similar sonic realms, he was a master of memorization who liked to sprinkle his lyrics with advertising taglines such as “American Express, don’t leave home without it” (this would often end many of his songs).

These taglines and the companies they came from filtered into Wesley’s artwork. You can see ads on the sides of buses or billboards in the Chicago skylines. A drawing coming up for auction in Modern Design + Post-War & Contemporary Art on February 25 has the McDonald’s “Arches” featured prominently. In other sections of many of Wesley’s drawings, advertising phrases are featured with these logos.

Wesley Willis (American, 1963-2003)
The Chicago Skyline, Wells, Wentworth 51st (McDonald’s), ballpoint pen and marker on Crescent board, 28″ x 41″
Toomey & Co. Auctioneers, Modern Design + Post-War & Contemporary Art, February 25, 2021, Lot 12
Estimate $600-800

The Growing Legacy of Wesley Willis


Complicated yet accessible, rough-around-the-edges yet good-natured, meticulous yet prolific, the immensely talented Wesley Willis is worthy of an artistic dissertation. You may visit Toomey & Co.’s website to view all of the Willis drawings that we have featured. At the moment, the market for his work is particularly strong. With each passing year, Willis has gradually begun to receive his just due posthumously for the work that he produced. This account only scratches the surface of who Willis was as a person and a creator. Writing this has made me want to “head butt” him again softly to reconnect our minds. RIP Wesley.