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Wicker Park, Bucktown, West Town

Chicago Icon Wesley Willis’ Vibrant Cityscapes Come To West Town In ‘City of Many Dreams’ Art Exhibit

The work of the late Chicago cult-favorite artist and underground musician brings spirited color and a deep affection for the city to Matthew Rachman Gallery.

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WEST TOWN — The work of late Chicago cult-favorite artist and underground musician Wesley Willis brings some spirited color and a deep affection for the city to a West Town gallery.

“Wesley Willis: City of Many Dreams,” opening Friday at Matthew Rachman Gallery, 1659 W. Chicago Ave., will share a comprehensive collection of the drawings Willis made from 1981 to 1991.

The pieces in this show represent the earliest artwork Willis produced, including his very first drawing. Some of it has never appeared in public. The drawings come from the collection of T. Paul Young, an architect who met Willis in the ’80s and supported his artistic endeavors, introducing him to other young artists and architecture students.

In this show’s works, often drawn initially in blue pen, then colored with felt-tip markers or colored pencils, Willis shared his fascination — and incredible memory for — the Chicago he loved: its skyscrapers, trains, houses and expressways.

Wesley Will’s “Dan Ryan Expressway” (1984)

“He saw everything. … He loved buildings, he loved the city,” said Young, who welcomed the then 18-year-old Willis into the Illinois Institute of Technology studio where the architect taught. “He loved the fact that Chicago has this transportation network, whether it’s automobiles or trains or boats, he loved that shit. He just loved it. And he drew it.”

Wesley Willis’ “The Dan Ryan Expressway” (1984)

The show’s opening reception is 6-9 p.m. Friday. The exhibit then runs through Nov. 17. It will also feature sculpture from Willis’ brother Ricky Willis, an artist with Project Onward, a nonprofit that supports the work of artists with disabilities. A portion of the sculpture proceeds will go to Project Onward.

A South Side native, Wesley Willis gained much of his notoriety due to his utterly original music, which often involved just Willis and a keyboard sample, with titles like “Rock ‘n’ Roll McDonalds” and “I Whupped Batman’s Ass.”

Willis — who died in 2003, had schizophrenia and spent some time homeless — was known to Chicagoans as a gentle soul with an imposing frame (6-foot-5 and 300 pounds) who would sell his art and albums on the city’s streets. His recordings gained fans in the punk scene, including former Dead Kennedys lead singer Jello Biafra, who helped get some of Willis’ work recorded.

Willis gained fans “because of the cathartic effect his unfettered emotional outbursts shared with punk’s raw energy,” the L.A. Times said in an obituary after Willis’ 2003 death from leukemia.

Many listeners also found humor in Willis’ lyrics, delivery and overall song structure. He sang about fast food, favorite bands, Al Capone, Oil Express and his own struggles with “the demon” he said tortured him with “hell rides” — a product of his schizophrenia. Usually, his only accompaniment came from factory-installed keyboard samples. That amused fandom led some critics to wonder if recording and distributing the songs of a man with schizophrenia was exploitative.

But Willis was beloved in the underground Chicago music scene in the 1990s, known as a “outsider musician” and a joyous fan, who usually wrote a song about shows he attended. He’d greet fans with gentle headbutts, a habit that left a permanent bruise on his forehead, MTV News said in an obituary. He was known for walking around the Wicker Park neighborhood selling recordings.

Willis’ musical career — which included 50-plus often self-produced albums and tours with his punk band, the Wesley Willis Fiasco — only came later in Willis’ life, though. He took to a keyboard in 1992 and gained fame in the later ’90s. Before that, Willis was an equally self-directed artist in the visual realm. Matthew Rachman Gallery wanted to share that early work with the world, the gallery’s owner said.

“We want Wesley Willis, the artist, to be known for his illustrations,” said Matthew Rachman. “So it’s important again that we bring these illustrations out, especially the early ones that kind of defined his career moving forward, and let them be seen.”

Wesley Willis’ “Lakefront”

Willis’ early work impressed architecture students and teachers at IIT, where the budding artist sold his drawings, Young wrote in a piece accompanying the show. The artworks often portray aerial views of Chicago streets and buildings, or lines of trucks or train cars seen from an angle.

“[S]tudents and faculty … were both shocked and amazed at his talent,” Young wrote. “Landscape architect Alfred Caldwell, whose studio was situated next to mine, adored Wesley’s colored pencil drawings and his perspective drawing ability.”

Wesley Willis’ “Rail Action” (1985)

The idiosyncratic color choices and verve of Willis’ cityscapes — sometimes with a building of his own creation plunked into the middle of the Chicago skyline — mix a playfulness with that evident skill, art critic Carrie McGath wrote

“[H]is 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,” she said. “The works are raw and kinetic portraits of the urban landscape portrayed with imagination but also a solid understanding of perspective and composition.”

Wesley Willis’ “The Chicago Cityscapes” (1984)

A true Chicago original, Willis’ outsize personality is what really makes the work, Rachman said.

“Wesley captured parts of the city in his own way that we owe a debt to. He shows us the city through the eyes of his persona,” Rachman said. “And I think it’s very real, the aspects and the views that he shows.”

Memories of that personality remain with Young, who kept in touch with Willis long after their chance meeting near IIT, when the architect saw Willis trying to sell a drawing. Though “things changed in his life” when violence at home triggered the onset of Willis’ schizophrenia, Young still remembers the 18-year-old he met in 1981.

“He was a very sensitive young man,” Young said. “And he loved to converse with people, strangers. He was a sweetheart.”

Here is some of the artwork being featured at the show:

Wesley Willis’ “The Dan Ryan Expressway” (1986)
Wesley Willis’ “Lake Michigan 31st Street Beach” (1983)
Wesley Willis’ “City of Many Dreams” (1991)

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