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Joy Ride: The Art, Music, and Character of Wesley Willis

Almost anyone in Chicago from the late 1980s into the early 2000s knew of the artist and musician Wesley Willis. A larger-than-life figure who created urban landscape drawings and composed, performed, and sold his unconventional music, he developed a fan base that remains dedicated to his work even after his death from leukemia in 2003.

“Wesley had a gravitational pull that few could resist: his size, wit, booming voice, charisma, and vulnerability made a potent and intriguing mix,” said Carla Winterbottom, Willis’s longtime friend and roommate. “When we lived in Wicker Park, musicians were always calling, dropping by, or planning gigs with Wesley. They admired his work ethic, his sense of humor, and his commitment to being a rock star without any doubts. He was omnipresent at hipster venues, gigs and parties, adding his unique mix of joyful banter, sales pressure, and head butts.” These head butts became a kind of signature, his way of showing love for friends and fans by tapping his forehead endearingly to theirs.

Willis on the porch at Wolcott apartment. C.1993. Photo credit Carla Winterbottom.

Willis on the porch at Wolcott apartment. C.1993. Photo credit Carla

Willis appreciated life, friendship, and art with an enviable abandon. Despite his battle with schizophrenia throughout adulthood, he was incredibly prolific in visual art and music. A psychotic breakdown following a robbery at gunpoint by his mother’s boyfriend triggered his ongoing illness. He heard demons in his head, particularly while riding buses and trains in and around Chicago. He referred to these diabolical moments as “hell rides.” His demons would yell obscenities and egg him on to be destructive. His friend Tamara Smith said “his ‘demons’ frequently tried to shut down his ‘joy ride’ by telling him to smash his CD players.”

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“1991 Dan Ryan.”

Music helped Willis combat or at least quiet these demons, and turn these “hell rides” into “joy rides.” Transportation was a large part of Willis’ daily life, and so he was drawn to the Dan Ryan Expressway, the busy artery that connects central downtown Chicago with its outlying neighborhoods. His artwork celebrates the freeway’s energy as the angular skyline and boxy buildings buoy in the distance. Drawn with colored markers, his cross-hatched representations of the city have great depth while also appearing to be whimsical: the roads are brown, the clouds are white puffs, and the train tracks alongside the expressway are yellow. The works are raw and kinetic portraits of the urban landscape portrayed with imagination but also a solid understanding of perspective and composition.

Willis’s friend Bryan Wendorf said of his artwork and practice. “I think Wesley had some kind of photographic memory and could vividly recreate specific scenes he remembered. The specific details he recalled were astounding: license plate numbers, bus ads, etc.”

Smith talked about his near-obsession with certain subject matter such as downtown Chicago scenes and methods of transportation, especially trains. “He rarely drew people, but for Carla he drew a portrait of Frank Zappa, and Carla and I each have drawings Wesley did of himself.”

"1991 Dan Ryan."

“1991 Dan Ryan.”

The intense impact Willis had on the three friends I spoke with, along with so many others who bought his drawings, his music, or had a chance encounter with him, was evident. Winterbottom remarked, “As hard as his life was, I don’t think I’ve ever met anyone who expressed joy so purely, and I really miss being around him.”

Winterbottom met him in 1989 when she worked at Genesis Art Supply, a Chicago art supply store Willis frequented to both create and sell his work. Willis completely lived within his art, and his daily life was itself a kind of art as he tirelessly made music and drew cityscapes. Like his music, his drawings originated from a preoccupation of some kind, often having to do with modes of transportation, roads, and railways.

"Art Institute of Chicago."

“Art Institute of Chicago.”

Prolific as a solo musician, Willis also tirelessly wrote songs for The Wesley Willis Fiasco, a band that performed from the early to mid-1990s. Willis’s music was often autobiographical ( “Chronic Schizophrenia” and “He’s Doing Time in Jail”) while others were comic and profane (“Rock ‘n’ Roll McDonald’s” and “Suck a Caribou’s Ass” ).

Willis’s intuitive drive to constantly create visual art and music achieved a mythic quality for some of his fans. He would visit Kinko’s locations throughout Chicago and while he was on tour to type out his lyrics on the public computers. The music he added to his lyrics came from the built-in samples that were factory installed on his keyboards. His process was decidedly unique despite the “canned” melodies he used. Smith put him in contact with the Dead Kennedy’s lead singer. “I introduced Jello Biafra to Wesley’s music; [he] was an immediate fan and lifelong friend to Wesley. Jello compiled some of his favorite Wesley tracks on Wesley Willis’s Greatest Hits Volume I and II, put out on Jello’s label, Alternative Tentacles.”

With local and then national exposure, thanks mostly to Willis’s gift for marketing his work, he achieved a savant celebrity status as a solo performer and as the vocalist for the Wesley Willis Fiasco. “Wesley and the Fiasco were extremely popular when they were together,” Wendorf reflected. “Wesley’s style of writing and singing was so singular that it wasn’t something anyone could really copy.”

Typical day at the apartment on Wolcott. Photo credit Carla Winterbottom.

Typical day at the apartment on Wolcott. Photo credit Carla Winterbottom.

The reason people were drawn draw to Willis was pretty simple. He was kind and funny, and his art and music were infectious. Smith elaborated about his outgoing nature and how he interacted with people. “He loved to make people laugh and to pull them into his universe. He often asked people for their phone numbers and then he’d call them regularly. He would also tell people he met on tour that he would come to visit them– and much to their surprise, he did.”

Although Willis’ story is a fascinating urban tale peppered with trials and joys, what lingers is the work and memories he so indelibly stamped on Chicago and beyond. His meditative drawings are an ode to the city’s beauty and its harsh edge. His tenacity for creating art and his combustible, eccentric music that told his story and immortalized his friends just keep the joy rides going.