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Matthew S. Bailey

Painting & Drawing

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oil on linen

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oil on canvas

24"H x 18"W x 1"D



oil on panel



I currently live in the city of Milwaukee, Wisconsin, and have been here for the last few years. Before that, though, my wife and I spent eight years living in a small village (Koyuk) in the bush of Alaska. During this time my wife worked as a Special Ed. teacher while graciously allowing me to develop myself as an artist. It was during my time in Alaska that I began to truly cultivate my skills and contemplate creative possibilities.

Some stylistic and thematic unity is starting to emerge in my work and I plan to augment that more and more as time goes on. At the moment, though, my work consists largely of stylistic and thematic exploration: high brow, low brow, colorful, monochromatic, beautiful, ugly, raw, refined, direct, vague, seductive, repulsive, serious, humorous, and much in between. My guiding precept, so far, has been (what I call) the “why not?” rule. When I encounter a possible course of action I don’t ask myself “why?”… instead I ask myself “why not”? For me, the “why not” rule embodies the very spirit of creativity. I am certainly going to endeavor towards a more unified body of work, but I will always try to keep the “why not?” rule close at hand.

In my work I sometimes address issues of social justice, nonviolence, environmental concerns, etc. Sometimes I address these issues in a very direct way - while at other times I take a more oblique approach. Sometimes what I’m up to, though, is nothing more substantial than nonsensical fun and visual exploration. I work primarily in oil paint and graphite, but I’m also proficient in watercolor, colored pencil, casein, and acrylic.

I hope you enjoy looking at my work as much as I enjoy making it. If you are interested in making a purchase or commissioning me for a project you can reach my agent, Rebecca Keiser, by clicking “contact” above.



Nerve Cowboy (journal)

Creep Machine magazine

Synesthesia magazine

Juxtapoz magazine


Pump House Regional Art Center (Structures show, 2nd place) – La Crosse, Wisconsin

Timothy Cobb Fine Arts (various shows) – Milwaukee, Wisconsin

Baton Rouge Gallery (Surreal Salon 8 Exhibition) – Baton Rouge, Louisiana

Transfer Pizzeria Café (featured artist) – Milwaukee, Wisconsin

Café Blue (one artist show) – Wauwatosa, Wisconsin

Gallery 2622 (one artist show) – Wauwatosa, Wisconsin

Baton Rouge Gallery (Surreal Salon 7 Exhibition) – Baton Rouge, Louisiana

Arctic Trading Post (one artist show) – Nome, Alaska


figure50.com - national showcase of figurative art: chosen for the state of Wisconsin

artcompetition.net – Faces of Humanity: first place

manifestjustice.org – Manifest Justice art contest: runner up

gallery25n.com – international showcase of art focused on The Human Form - two of my works were chosen to be represented in 2 of the 7 categories: painting and drawing.


February 22 - April 25, 2017

Structures: Art of the Urban Landscape

Pump House Regional Arts Center, La Crosse, WI

Juried event, "air castle" selected for inclusion and won 2nd place in show

September 9 - October 7, 2016

Who Amongst Us?

Timothy Cobb Fine Arts Gallery, Milwaukee, WI

April 8 - June 2, 2016

Scapes of Land, City and Water

Timothy Cobb Fine Arts Gallery, Milwaukee, WI

January 3 - 25, 2016

Surreal Salon 8

Baton Rouge Gallery of Contemporary Art, Baton Rouge, LA

Juried event, "vision quest" selected for inclusion

February 6 - March 1, 2015

Gallery 2622

2622 N. Wauwatosa Ave.

prints available:http://relaxeder.deviantart.com/gallery/53063270/2622-show

January 2 - 24, 2015

Surreal Salon 7

Baton Rouge Gallery of Contemporary Art, Baton Rouge, LA

Juried event, "septic system" selected for inclusion

Content copyright by Matthew S. Bailey.