Keeping Up That Good Work
Wesley Willis' Chicago
Wesley Willis was a self-taught artist and South Side native known for his complex and vibrant drawings of downtown Chicago. Before he became a beloved figure on the underground music scene, Willis was a fervent and dedicated draftsman who captured the bustling city with large pen and ink drawings. A plein air artist, he could be found in The Loop — seated on a folding chair with sheets of paper spread over his lap — using the edge of pens to craft precise perspectives, both startlingly detailed and expressive. In 1988, producer Carl Hart featured the artist in a short documentary for Chicago public access.
Watch Wesley Willis: Artist of the Streets below.
Born in Chicago in 1963, Wesley Willis eventually became a fixture on the local outsider art and underground music scenes. Although he only had a small, cult following at first, Willlis' work has become more widely appreciated as of late. In particular, demand for his ballpoint drawings of Chicago has increased dramatically.
Willis' early years were quite unsettled. His parents fought often and separated, which led to Willis and his siblings living in various foster homes. During his twenties, Willis was robbed and threatened by his mother's boyfriend and subsequently diagnosed with schizophrenia. Although Willis began to hear voices and experience other maladies and tics, he also had a savant-like memory, which would ultimately benefit his art and music practices.
A creature of habit, Willis took up drawing seriously after repeated visits to the Illinois Institute of Technology (IIT), just a few blocks from where he lived in the Robert Taylor Homes, a public housing project in the Bronzeville neighborhood on the South Side of Chicago. Each weekday morning at 8:30 a.m., Willis met art historian Rolf Achilles, or George Danforth, IIT's former Dean of Architecture. They would get Willis a coffee and set him up in an office where he could draw or, later, play a Yamaha keyboard that they bought to keep him engaged.
Willis’ work is immediately recognizable. His signature ballpoint drawings have an active and quick architectural rendering style. He employed various perspective devices, distorting his subjects and breaking drawing “rules” whenever and however he wanted. He created consistently compelling, dense urban visuals that appear less busy upon closer inspection, with breadths of clouds regularly dominating low horizon lines. Usually working on Crescent board, Willis would take a section of the city of Chicago and render a large swath of his viewing angle. Some of his favorite vantage points were overlooking the Dan Ryan Expressway facing downtown and the 'L' train, Comiskey Park, The Loop, Grant Park's Buckingham Fountain, and the Lakeshore.
Far from being tangential to his drawing practice, Wesley’s music complemented and interacted with his visual art in many cases. Willis tends to incorporate language from advertising in a faithful yet playful manner. Buses almost always have realistic signage on their sides. Restaurants like McDonald's have their logos replicated carefully. His song lyrics borrow from McDonald's and American Express, whose tagline, "Don't leave home without it," ended many of his songs. Titles of his songs include "Rock 'n' Roll McDonald's," Scooby Dooby," and "I Whipped Batman's Ass."
In his lifetime, Willis never received wide acclaim for his work. He mostly sold his drawings for $20 or less on the streets of Chicago until he was later exhibited in small shows. His music career started in similar obscurity, but he went on to play at renowned venues like CBGB in New York City. As a solo artist, Willis sang jauntily over preset keyboard tracks, but he also toured with a punk group, The Wesley Willis Fiasco.
Willis passed away in 2003 at age forty from leukemia complications. Over the last two decades, his art and music have been reevaluated by critics and collectors alike. Today Willis' work is posthumously celebrated for its directness, humor, and sincerity. His drawings capture the essence of late-twentieth century Chicago and his music resounds with references to the absurdity of American consumer culture.
Auction Results Wesley Willis
The Dan Ryan Expressway — Past 51st St. toward 47th St., 1988
The Dan Ryan Expressway, past 51st, st. towards 47th, St., 1987
The Newberry Library, Clark St. Dearborn St., 1987