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Wesley Willis

American · 1963–2003 · Illustrator

Wesley Lawrence Willis was an American musician and visual artist. Diagnosed with schizophrenia in 1989, Willis began a career as an underground singer-songwriter in the… (Wikipedia)

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68lots offered2009–2025years recorded99%sold (66)$1.8kSign up free to seemedian price

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The Dan Ryan Expressway Past 39th Toward 35th St.Wright · Jul 2023$4,585≈ £3,552≈ €4,160Sign up to see
The Lakefront Sept 25, 1983Wright · Apr 2021$3,750≈ £2,704≈ €3,113Sign up to see
The Shore LineWright · Jul 2023$3,612≈ £2,798≈ €3,277Sign up to see

Wesley Willis’s highest prices recorded at auction, ranked in US dollars at each sale-date exchange rate and shown in the currency of the sale (with the buyer’s premium where the house publishes it).

Lot images as published by each auction house (67 lots with an image). Images from houses that reserve their photographs are shown as small thumbnails linking to the house’s site.

Wesley Willis, Chicago River, 1991, marker and ballpoint pen on Crescent — Chicago River, 1991
Wright · Dec 11, 2025
$1,905Sign up free to see

Wesley Willis, The Dan Ryan Expressway 51st. St., 1991, ballpoint pen and marker on Crescent — The Dan Ryan Expressway 51st. St., 1991
Wright · Jun 18, 2025
$3,556Sign up free to see

Wesley Willis, Untitled (View from I-94 Chicago), 1990, ballpoint pen on Crescent board — Untitled (View from I-94 Chicago), 1990
Wright · Feb 20, 2025
$1,254Sign up free to see

Wesley Willis, Michigan Av., 1988, ballpoint pen and marker on Crescent — Michigan Av., 1988
Wright · Oct 1, 2024
$1,935Sign up free to see

Wesley Willis, Untitled (Chicago scene), 1987, ballpoint pen, marker and colored pencil on Crescent board — Untitled (Chicago scene), 1987
Wright · Oct 1, 2024
$1,226Sign up free to see

Wesley Willis, Chicago River, 1991, marker and ballpoint pen on Crescent — Chicago River, 1991
Wright · Jun 18, 2024
$1,260Sign up free to see

Wesley Willis, Sox Park, 1991, marker and ballpoint pen on Crescent — Sox Park, 1991
Wright · Jun 18, 2024
$917Sign up free to see

Wesley Willis, Dan Ryan Expressway Looking Off 51st Street Toward 47th Street, 2003, ballpoint pen and marker on Crescent — Dan Ryan Expressway Looking Off 51st Street Toward 47th Street, 2003
Wright · Feb 23, 2024
$1,197Sign up free to see

Wesley Willis, Lake Shore Drive, 1991, ballpoint pen, marker and glossy medium on Crescent — Lake Shore Drive, 1991
Wright · Feb 23, 2024
$1,764Sign up free to see

Wesley Willis, The Downtown Chicago Skyline Halsted St. at Madison, 1986, ballpoint pen and marker on Crescent — The Downtown Chicago Skyline Halsted St. at Madison, 1986
Wright · Feb 23, 2024
$1,441Sign up free to see

Wesley Willis, The Dan Ryan Expressway, Past 51st. Toward 47th. St., 1991, ballpoint pen and marker on Crescent board — The Dan Ryan Expressway, Past 51st. Toward 47th. St., 1991
Toomey & Co. · Jul 26, 2023
$1,806Sign up free to see

Wesley Willis, The Dan Ryan Expressway Past 51st. St. Toward 47th St., 1987, ballpoint pen and marker on Crescent board — The Dan Ryan Expressway Past 51st. St. Toward 47th St., 1987
Toomey & Co. · Jul 26, 2023
$1,419Sign up free to see

Wesley Willis, The Chicago White Sox Stadium, 1992, ballpoint pen, marker and matte medium on Crescent board — The Chicago White Sox Stadium, 1992
Toomey & Co. · Jul 26, 2023
$1,441Sign up free to see

Wesley Willis, The Dan Ryan Expressway, 1985, ballpoint pen and marker on Crescent board — The Dan Ryan Expressway, 1985
Wright · Jul 12, 2023
$2,772Sign up free to see

Wesley Willis, The Dan Ryan Expressway Past 39th Toward 35th St., 1991, ballpoint pen, marker and medium on Crescent board — The Dan Ryan Expressway Past 39th Toward 35th St., 1991
Wright · Jul 12, 2023
$4,585Sign up free to see

Wesley Willis, The Dan Ryan Expressway Past 51st. Toward 47th St., 1989, ballpoint pen and marker on Crescent board — The Dan Ryan Expressway Past 51st. Toward 47th St., 1989
Wright · Jul 12, 2023
$2,142Sign up free to see

Wesley Willis, The Shore Line, 1993, ballpoint pen, marker and medium on Crescent board — The Shore Line, 1993
Wright · Jul 12, 2023
$3,612Sign up free to see

Wesley Willis, Soldier Field, 1993, ballpoint pen and marker on Crescent board — Soldier Field, 1993
Toomey & Co. · Apr 19, 2023
$1,764Sign up free to see

Wesley Willis, The Dan Ryan Expressway 51st St., 1987, ballpoint pen and marker on Crescent board — The Dan Ryan Expressway 51st St., 1987
Toomey & Co. · Apr 19, 2023
$3,024Sign up free to see

Wesley Willis, The Dan Ryan Expressway 57th St. through 47th St., 1985, ballpoint pen and marker on Crescent board — The Dan Ryan Expressway 57th St. through 47th St., 1985
Toomey & Co. · Apr 19, 2023
$1,764Sign up free to see

Wesley Willis, The Shore Line, 1987, ballpoint pen and magic marker on Crescent — The Shore Line, 1987
Toomey & Co. · Apr 19, 2023
$968Sign up free to see

Wesley Willis, Chicago Sun Times, 1990, ballpoint pen, marker and medium on Crescent board — Chicago Sun Times, 1990
Toomey & Co. · Apr 19, 2023
$1,890Sign up free to see

Wesley Willis, Chicago North Western Container Yard, 1991, ballpoint pen and marker on Crescent board — Chicago North Western Container Yard, 1991
Toomey & Co. · Apr 19, 2023
$1,008Sign up free to see

Wesley Willis, The Shoreline, 1991, ballpoint pen and marker on Crescent board — The Shoreline, 1991
Toomey & Co. · Apr 19, 2023
$3,024Sign up free to see

Wesley Willis, Chicago River, 1991, marker and ballpoint pen on Crescent — Chicago River, 1991
Toomey & Co. · Oct 11, 2022
$1,188Sign up free to see

Wesley Willis, Chicago River Congress Expressway, 1987, ballpoint pen and magic marker on Crescent — Chicago River Congress Expressway, 1987
Toomey & Co. · Oct 11, 2022
$1,750Sign up free to see

Wesley Willis, The Chicago River, 1991, ballpoint pen, marker and matte medium on Crescent — The Chicago River, 1991
Toomey & Co. · Oct 11, 2022
$1,430Sign up free to see

Wesley Willis, The Shore Line, 1993, ballpoint pen, marker and medium on Crescent board — The Shore Line, 1993
Toomey & Co. · Oct 11, 2022
$3,000Sign up free to see

Wesley Willis, Buckingham Fountain, 1990, ballpoint pen and marker on Crescent — Buckingham Fountain, 1990
Toomey & Co. · Oct 11, 2022
$1,430Sign up free to see

Wesley Willis, 400 West Erie, ballpoint and marker on Crescent — 400 West Erie
Toomey & Co. · Oct 11, 2022
$975Sign up free to see

Wesley Willis, The Dan Ryan Expressway, Root St., 1999 — The Dan Ryan Expressway, Root St., 1999
Toomey & Co. · May 18, 2022
$2,500Sign up free to see

Wesley Willis, Chicago Skyline, 1992 — Chicago Skyline, 1992
Toomey & Co. · Apr 6, 2022
$2,080Sign up free to see

Wesley Willis, The Dan Ryan Expressway, 1984 — The Dan Ryan Expressway, 1984
Toomey & Co. · Dec 2, 2021
$2,210Sign up free to see

Wesley Willis, The Dan Ryan Expressway, 1985 — The Dan Ryan Expressway, 1985
Toomey & Co. · Dec 2, 2021
$2,210Sign up free to see

Wesley Willis, Chicago River Civic Center, 1988, ballpoint pen and felt marker on artboard — Chicago River Civic Center, 1988
Wright · Oct 6, 2021
$1,875Sign up free to see

Wesley Willis, Day Time (N. Michigan Ave.), 1988, pen and felt marker on artboard — Day Time (N. Michigan Ave.), 1988
Wright · Oct 6, 2021
$1,500Sign up free to see

Wesley Willis, The Chicago Skyline Seen from McComick Inn, 1984, pen and felt marker on artboard — The Chicago Skyline Seen from McComick Inn, 1984
Wright · Oct 6, 2021
$2,250Sign up free to see

Wesley Willis, The Dan Ryan Expressway Past 37th Toward 35th Street, 1988, pen and felt marker on artboard — The Dan Ryan Expressway Past 37th Toward 35th Street, 1988
Wright · Oct 6, 2021
$2,000Sign up free to see

Wesley Willis, The Chicago Skyline Lake Michigan, 1988, pen and felt marker on artboard — The Chicago Skyline Lake Michigan, 1988
Wright · Oct 6, 2021
$1,560Sign up free to see

Wesley Willis, Night Time (N. Michigan Ave.), 1988, pen and felt marker on artboard — Night Time (N. Michigan Ave.), 1988
Wright · Oct 6, 2021
$1,560Sign up free to see

Wesley Willis, The Dan Ryan Expressway Past 39th Toward 35th St., 1988, pen and felt marker on artboard — The Dan Ryan Expressway Past 39th Toward 35th St., 1988
Wright · Oct 6, 2021
$2,375Sign up free to see

Wesley Willis, Jackson, Adams, Franklin, 1989; 109th and S. Cottage Grove Av., 1989 — Jackson, Adams, Franklin, 1989; 109th and S. Cottage Grove Av., 1989
Toomey & Co. · Aug 12, 2021
$1,560Sign up free to see

Wesley Willis, The McCormick Place McCormick Place Expansion — The McCormick Place McCormick Place Expansion
Toomey & Co. · Aug 12, 2021
$1,430Sign up free to see

Wesley Willis, The Chicago White Sox Stadium, 1992 — The Chicago White Sox Stadium, 1992
Toomey & Co. · Aug 12, 2021
$1,950Sign up free to see

Wesley Willis, The Lakefront, 1988 — The Lakefront, 1988
Toomey & Co. · Aug 12, 2021
$3,120Sign up free to see

Wesley Willis, The Chicago Skyline, 1988 — The Chicago Skyline, 1988
Toomey & Co. · Aug 12, 2021
$2,625Sign up free to see

Wesley Willis, The Dan Ryan Expressway, 35th Street, 1989 — The Dan Ryan Expressway, 35th Street, 1989
Toomey & Co. · Aug 12, 2021
$2,250Sign up free to see

Wesley Willis, The Dan Ryan Expressway — Past 51st St. toward 47th St., 1988 — The Dan Ryan Expressway — Past 51st St. toward 47th St., 1988
Toomey & Co. · Aug 12, 2021
$2,470Sign up free to see

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