Abstract painting by Chicago artist John Dempsey featuring layered black gestural lines and colorful geometric forms on a predominantly white ground.

JOHN DEMPSEY

Chicago Contemporary Artist

John Dempsey is a Chicago-based contemporary artist whose abstract paintings draw from graffiti, street typography and the visual language of the city. Working in oil, acrylic and spray paint with hand-cut stencils, Dempsey builds layered compositions where line, shape and gesture move between structure and spontaneity.

His work reflects a fascination with urban mark-making — fragments of language, accidental compositions and visual collisions found in the urban landscape. Dempsey also creates figurative paintings under the artist name Billy Tokyo, a parallel body of work influenced by the Chicago Imagists, Japanese visual culture, cartooning and contemporary urban life.

Abstract painting by John Dempsey featuring layered black lines, organic white forms and colorful geometric shapes against a green background.

SELECTED WORK

Spring Floral I by John Dempsey, an abstract oil painting with interlocking white organic forms and accents of pink, green, orange and yellow on a gray ground.

Spring Floral 1
Oil on panel · 2026 · 17 × 15 in.

A Landscape of a Thought by John Dempsey, an abstract painting of layered gestural marks, colorful stencil forms and brushwork on a predominantly white ground.

A Landscape of a Thought
Acrylic, oil and spray paint (using stencils) on canvas · 2025 · 54 × 78 in.

Where the Heavens Touch Earth by John Dempsey, an abstract painting featuring sweeping black lines, white organic forms and blue and earth-toned accents.

Where the Heavens Touch Earth
Oil on canvas · 2026 · 26 × 42 in.

VIEW ABSTRACT WORK
Nature Exhaling by John Dempsey, an abstract oil painting of layered white organic forms, black gestural lines and colorful shapes against a light blue ground.

Nature Exhaling
Oil on panel · 2026 · 17 × 15 in.

BILLY TOKYO

A Parallel Visual Language

Billy Tokyo is the figurative alter ego of Chicago artist John Dempsey — a parallel body of work combining influences from the Chicago Imagists, Japanese visual culture, cartooning and contemporary urban life.

Hot City Day by Billy Tokyo, the figurative alter ego of John Dempsey, depicting a densely layered imagined city filled with buildings, figures and graphic forms.

Hot City Day
Acrylic, oil and spray paint (using stencils) on canvas · 2025 · 48 × 72 in.

Here We Are by Billy Tokyo, the figurative alter ego of John Dempsey, depicting a crowded urban world of figures, buildings, vehicles and graphic forms with social commentary.

Here We Are
Acrylic, oil and spray paint (using stencils) on canvas · 2025 · 36 × 40 in

EXPLORE BILLY TOKYO
Colorful illustration of numerous cartoon characters at a beach, including people in swimsuits, caricatured faces, animals like ducks, and abstract figures, with a boat and a sailing ship in the ocean, all depicted in a playful, abstract style.

At The Beach
Acrylic, oil and spray paint (using stencils) on canvas · 2025 · 30 × 40 in.

NOTES FROM THE STUDIO

Thoughts on painting, creativity, art history and the strange rituals of being an artist.

Two stages of a John Dempsey artwork, showing an initial line drawing beside the developed painting with added color and layered abstract forms.

The Artist’s Pursuit of Originality

In a world where images can be created almost instantly, what does it mean for an artist to be original? This essay looks at the lifelong pursuit of finding an individual voice, and the possibility that originality isn’t about creating something no one has ever seen, but about making something that could only have come from you.

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CHICAGO STUDIO

Studio visits by appointment.

355 North Laflin Street
Chicago, IL 60607
Fulton Market District

CONTACT JOHN DEMPSEY →

Sketchbook drawing by Billy Tokyo featuring a stylized figure beside a pink futuristic car surrounded by geometric architectural forms.

The Importance of a Sketchbook

Some of the most important work an artist makes will never hang on a wall.

It lives in sketchbooks—in unfinished drawings, strange experiments, bad ideas and accidental discoveries. Picasso filled 175 sketchbooks and once wrote, “I am the sketchbook.”.

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Art in Theory 1900–2000 on an artist’s worktable surrounded by paint tubes and art materials.

A Very Short History of Art Theory

This is a very short history of art theory—from Plato to Picasso, cave paintings to conceptual art—and why, after thousands of years of thinking about art, sometimes the best thing we can still do is simply look.

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