Break the Ice: How to Paint a Complete Stranger’s Portrait

In the Winter 2016 issue of Acrylic Artist we feature portrait painter Matt Cauley who is changing the face of portraiture. Instead of painting C-level executives and the well-to-do society scions in thoughtful, symbolically rich poses and settings, Cauley’s portrait subjects are the everyday men and women he sees on the street, the subway or perhaps in the neighborhood coffee shop. Securing subjects for his paintings forces him to face one of his fears—something many artists dread—approaching a stranger you want to paint.

We caught up with Cauley and spent some time talking about approaching strangers, how not to fear rejection and learning to go with the flow. Here’s our conversation.

Morning Sludge (acrylic on canvas, 20x30) Matt Cauley, Acrylic Artist

Morning Sludge (acrylic on canvas, 20×30) Matt Cauley, Acrylic Artist

Acrylic Artist: Do you remember the first time you approached a stranger you wanted to paint? What was her/his reaction?
Matt Cauley: The first time I approached a complete stranger my wife and I were out getting coffee at our local deli. It was bitter cold outside with snow falling pretty heavily and it was fairly crowded and noisy inside the coffee shop.

As we were in line, I saw a woman near the window who had just sat down with her cup of coffee. Her face was pale, her nose a bit runny and a brilliant bright red, and her hair was slightly disheveled. You could tell the winter weather had hit her hard that morning. Yet, she had the look of pure enjoyment on her face as she was about to take her first sip of wonderfully delicious coffee. It was such a calming, soothing expression—the same serenity I think we all feel when we take that first sip, especially on a wintery day.

I mentioned to my wife that visually it would make an excellent painting. She agreed and encouraged me to go over and give the woman my card. I was hesitant at first; my natural inclination is to not bother someone out of the blue, especially in a crowded or noisy environment. The next thing I knew,  I was navigating over because I really wanted to make that painting happen.

On my way over to her my heavy jacket snagged the Little Debbie Snack Cake display and I nearly toppled the entire thing. It was a little embarrassing, yet I did my best not to let it rattle me.

I politely asked the lady if I could bother her for a moment—quickly introducing myself as a portrait and figure painter. I explained to her that I was always on the lookout for interesting subjects to paint. As I reached for my card I couldn’t help but feel a bit like a pushy salesman, so I tried to keep it a no-pressure situation.

AA: I can imagine that is not what she was expecting to happen while enjoying her morning coffee. What was her reaction?
MC: She seemed receptive to at least the idea of a painting. I didn’t ask for her information, but rather I left her a card with my email and portfolio information. I invited her to check out my work, and if she liked what she saw, to please contact me. She reached out a few days later, expressing interest in taking part in my next project.

Revised Storylines

AA: And, as we can see in Morning Sludge, the meeting was a success. The painting looks just as you describe that first encounter. Have you ever misread a person and created a storyline that was out of character for your subject?
MC: Oh, sure. One time I thought I had the perfect visual lined up for someone. Yet, after I presented the idea she felt I’d really missed the mark on her character. I was envisioning a very stiff, gothic, almost Tim Burton-type of portrait. As it turned out, that wasn’t her personality at all. l didn’t want to completely dismiss the idea, so I reworked the approach to match her subtle, quietly sly demeanor. Something unexpected developed through that compromise and the resulting painting was quite good. That’s one of the joys of incorporating the subject’s story and personality into the painting.

AA: Has anyone ever turned down your request to paint their portrait?
MC: On occasion. Sometimes they simply aren’t comfortable being depicted in a painting. A few times a subject’s own insecurities made them feel uncomfortable with the idea. Recently I asked a fellow artist to sit for me. Although she loved my work, she explained that she was still trying to figure herself out. Therefore, she wasn’t sure if she was comfortable with someone else “defining her” artistically before she did so herself.

Fresh Starts

AA: Do you have to scrap the idea if the subject says no or do you look for a substitute, a lookalike or understudy of sorts?
MC: If someone says no, I will look for alternate subjects for different projects, but never lookalikes. If anything, 50 percent of each painting draws inspiration from the person’s own story. When I shift gears with a new model the painting concept adjusts accordingly. The original idea gets put on the back burner on the chance I can ever revisit it with the intended subject.

AA: Is it safe to assume that a person’s insecurities are why they decline your offer?
MC: Definitely, a few have declined due to their body-image issues. On the other hand, sometimes that insecurity is exactly why they want to sit for me. People have shared that by sitting for me, they hoped they would better deal with, if not overcome, their negative body issues. The process can be therapeutic, therefore I never try to convince a potential subject if they’re just not ready. It’s better to let them know the invitation is always there. I tell them I can tailor the project to fit their comfort level should they want to sit for me in the future.

Words of Wisdom

AA: What advice do you have for an artist who hasn’t asked a stranger to be a part of their art?
MC: I would suggest asking friends and neighbors to sit first. Get a little bit of that confidence built up, along with the experience that goes with it. The more confident you are in the proposal, the more confident your subject will feel about the project. Even if they say no, that’s still a positive. You’ll learn more about why people might turn down your project and how to improve your proposal process.

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