Keeping Up That Good Work

Wesley Willis's 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 in 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. The drawing Willis is working on in the film is offered here as Lot 390

Watch Wesley Willis: Artist of the Streets below.