Life Is Too Short to Be Just One Artist

On painting as John Dempsey, becoming Billy Tokyo, and how working under two identities changed the way I think about art.

For most of my life, I painted under my own name. John Dempsey. It seemed reasonable enough. It was, after all, my name.

Over the years, John Dempsey accumulated all the things an artist is supposed to accumulate: influences, habits, techniques, successes, failures, expectations and, perhaps most dangerously, an idea of what a John Dempsey painting was supposed to look like.

That last part can become a problem.

Once you have painted long enough, you develop a history. Eventually that history starts following you into the studio. You begin a painting and, without realizing it, thirty years of previous paintings are standing behind you, watching.

That's not really what you do. That's not your style. People won't know that's yours.

This is one of the strange traps of becoming an established artist. You spend years trying to develop a recognizable style, and then one day you realize you've succeeded.

Now you have to escape from it.

My escape route was a guy named Billy Tokyo.

Even the name came from the collision I saw happening in the work.

Billy was Western. Tokyo was Eastern.

The early images were a mash-up of those two visual worlds—Western outsider and cartoon art colliding with the exaggerated sweetness of Japanese anime, particularly the over-the-top, bubble-gum cuteness that could somehow be both innocent and slightly unsettling at the same time.

So Billy Tokyo seemed like the right name.

It sounded a little like a person who might actually exist and a little like someone I had completely made up.

Which, as it turned out, was exactly what he was.

Billy didn't actually begin as some grand experiment in artistic identity. He began much more commercially.

The earliest Billy Tokyo work was vector-based illustration and design—bright, graphic and meant to live in a very different world from the paintings I was making under my own name. I developed artwork for clients and projects including Lollapalooza and the Chicago Cubs. There was something fun about working this way. It was immediate, graphic and unburdened by any expectation that it had to resemble the art I was already known for making.

Billy Tokyo could do things John Dempsey couldn't.

Or maybe more accurately, things John Dempsey wouldn't.

But somewhere along the way, Billy started getting ideas above his station.

The work became less commercial. The computer gave way to painting. The imagery became stranger and more personal. Buildings began leaning. Figures appeared. Narratives developed. Humor became darker. And the work increasingly absorbed something that had always fascinated me—the wonderfully peculiar tradition of Chicago figurative art.

The Chicago Imagists became an especially strong influence.

I have always loved the freedom in that work: the strange characters, aggressive color, humor, vulgarity, beauty, comics, advertising, outsider art and visual noise all colliding without anyone seeming particularly worried about whether they belonged together.

Billy Tokyo felt at home there.

What had begun as a commercial pseudonym gradually became something I hadn't anticipated.

Billy became an artist.

And once that happened, something even more interesting happened to me.

I got to start over.

Billy Tokyo hadn't gone to art school. Billy hadn't won anything. He'd never had a successful painting.

More importantly, he'd never had an unsuccessful one.

He had no collectors to disappoint, no body of work to remain consistent with and no reason whatsoever not to make something ridiculous. He had no artistic history.

I found that incredibly liberating. For the first time in years, I was an absolute beginner again.

I think artists underestimate how valuable it is to occasionally become a beginner. We spend so much of our lives learning how to paint that eventually knowing how to paint can become part of the problem.

Technique becomes habit. Habit becomes style. Style becomes identity. And identity, if you're not careful, becomes a fence.

Billy Tokyo allowed me to climb over mine.

When I worked on those paintings, I found myself asking a wonderfully stupid question: What would Billy Tokyo do?

Not what would I do. Billy.

It sounds slightly insane when I write it down. Perhaps it is. But creativity has always benefited from a little temporary insanity.

Billy could use colors I might not use. He could distort perspective. He could make buildings lean at impossible angles. He could put something funny next to something disturbing. He could borrow from comics, graffiti, advertising, the Chicago Imagists and whatever other visual debris happened to be floating around in my head.

Most importantly, he could fail.

If the painting was terrible, what did I care? Billy painted it.

This arrangement worked beautifully for me and rather unfairly for Billy.

There was another reason I needed him. Painting one kind of picture simply wasn't enough.

I admire artists who spend their entire lives digging deeply into one visual language. There is something heroic about that kind of concentration. I'm apparently not built that way.

There are things I want to say through abstraction that become obvious or heavy-handed when rendered figuratively. And there are things I want to say about people, cities, politics, absurdity and contemporary life that cannot easily be squeezed into an abstract painting.

So I stopped trying to choose.

John Dempsey could paint one world.

Billy Tokyo could paint the other.

Oddly enough, the longer they worked beside each other, the more I began to realize they were painting the same world.

My abstract paintings often contain brightly colored shapes that stack, lean, collide and balance against one another. I like the feeling that everything is holding together—but only barely.

One form supports another. Something pushes against something else. A shape appears to be carrying more weight than it reasonably should. Remove the wrong piece and you suspect the entire arrangement might collapse.

I suppose that is how I see society.

We build systems on top of systems. People depend upon people. Institutions lean against institutions. Everything appears solid until suddenly it doesn't.

There is tension in the paintings, but there is also optimism. Somehow the pieces keep balancing. At least for now.

Then I walk across the studio and look at a Billy Tokyo painting.

There are buildings leaning sideways. Some have already fallen over. Others appear to be propped up by something that could not possibly support them. People wander through these unstable cities, frequently distracted by their phones, apparently unconcerned that the entire civilization behind them seems to be tilting.

And I think: Oh. He's doing it too.

The vocabulary changed. The subject didn't.

John Dempsey stacks abstract forms. Billy Tokyo stacks buildings.

Both seem preoccupied with what happens when complicated things are held together under questionable circumstances.

Apparently neither of us trusts structural engineering.

This is one of the things I find most fascinating about making art. You can change your style, your materials, your palette. You can even change your name.

But apparently it is much harder to escape yourself. Whatever genuinely interests you has a way of resurfacing. Maybe style isn't really what defines an artist after all. Maybe style is simply the clothing an idea wears.

One day the idea shows up in an abstract painting wearing a very nice suit. The next day it comes through the door dressed as Billy Tokyo. But it's still the same guest.

There have been moments when the arrangement becomes confusing. I have literally started signing a painting with the wrong name.

There are also paintings that seem to exist somewhere between the two identities, and I am never entirely sure who made them.

I like those paintings.

They suggest that the border is becoming porous.

Because I don't really want Billy Tokyo to become another rigid style. That would defeat the entire purpose. The moment I start thinking, This is what a Billy Tokyo painting is supposed to look like, I've simply built myself another fence.

Then I'll probably have to invent a third artist. And frankly, two of us already take up enough room in the studio.

What began as a commercial pseudonym eventually taught me something important about creativity. Sometimes you have to give yourself permission to become someone you have never been before. Artists talk endlessly about finding their voice. I'm no longer certain we should have only one.

Why shouldn't an artist contain contradictions? Why can't one part of you want abstraction and another want narrative? Why can't one painting be beautiful and another sarcastic? Why can't you spend Saturday morning carefully balancing shapes on a canvas and Sunday afternoon painting a collapsing city filled with people staring at their phones?

We contain all of those things ourselves. It seems unreasonable to expect our paintings to be less complicated than we are. Perhaps that is what Billy Tokyo ultimately gave me. Not another identity, exactly. Permission.

Permission to make something that didn't look like what I had made before. Permission to be bad at something again. Permission to follow an idea without worrying about whether it belonged to the career of the artist I had already become.

And eventually I discovered something I hadn't expected.

The farther I allowed Billy Tokyo to wander away from John Dempsey, the more obvious it became that the two of them had been looking at the same things all along.

They just found different ways to paint them. One uses shapes. The other uses buildings. Both are trying to keep the whole thing from falling over. So far, they're managing. Barely. And I think that's the point.