Drawing Incognito: Being an Undercover Artist

Subway portrait drawings by Robin Kappy

Have you ever played the part of an “undercover artist” inconspicuously using the public as your art models? Anybody can do it, but do you dare? Whenever I sketch a stranger it’s an adrenaline rush of fun and fear. I’m always concerned people won’t be happy if they discover me looking at them; and if they do catch me, what would they think of my art? I can be such chicken when drawing strangers. Many of my artist friends do this sort of thing all the time. So, in hopes that I catch some of their boldness, I asked a few of them about their experiences drawing incognito. Below are their thoughts and my own.

In·cog·ni·to: adjective & adverb, having one’s true identity concealed

What is it that entices us to draw people in public? Rather than trying to create a natural looking scene, the scene is natural and ready for us to create. Secret sketching has levels: Beginner, Intermediate, and Advanced. I’m not rating by artistic skill rather I’m grading by difficulty and “fear-factor” (i.e. the likelihood that you’ll be caught). What is a good Beginner level activity? This I do all the time- Draw people giving lectures or speeches. I give it a zero fear-factor rating. They spot you looking at them? Good, you’re supposed to be, right? It will look like you’re taking notes. You won’t feel too rushed either considering that usually, you know how long a speech will last. Another plus to this Beginner activity, while many think doodling is an act of zoning out it can actually help you listen to and absorb the lecture better.

Drawing a sleeping stranger I would rate as an Intermediate level activity. An artist I know told me stories of when she was in college how she’d go to the library and draw the students who were asleep. She’d use it as a speed drill. “It would improve my drawing skills! I had to simplify to quick finish before they moved. And if they moved- I’d start a new drawing.” She would then sign her sketch “Masked Marauder” and leave it on the student as a funny gift for them to wake up to.

You can’t do sketches enough. Sketch everything and keep your curiosity fresh. John Singer Sargent

If you follow me online you know I recently took a long train ride. No matter the updated interiors of trains they still run on the same old tracks, so to me it feels like a trip back in time; a black & white movie and I’m an artist spy. On my journey, the young man sitting across the aisle from me reclined his chair and fell asleep. I had a choice: enjoy the early Autumnal views zooming past OR pull out my drawing pad and get to work. I choose the later.  I felt sneaky, thinking “What if I’m caught?” Is that part of the fun? I didn’t know how long I had or if my sleeping subject would stay still. About 30 minutes into drawing a train attendant suddenly appeared in front of me blocking my view. I snapped back to reality. Was I being reprimanded? To my relief- no. He knew I was an artist (well there goes my cover!) and simply wanted to talk about it. I showed him my drawing, and he showed me a magic trick. Life is funny. Below is my drawing.

New York City artist Robin Kappy regularly draws people while riding the subway. This is an Advanced level activity: Close quarters, people rushing from one stop to the next, giving you perhaps just moments with them, and not much opportunity to be sly about it. Despite the seemly hectic atmosphere Robin captures reposeful faces of her fellow passengers. *See her subway drawings at the top of this article* I asked Robin, why draw people on the subway?  “Because they are beautiful in the soft light and I love diversity and a sense of each person’s character, lifestyle, mood, and history.” In busy spaces with nowhere to hide you must be fearless and fast… and I think it helps to have that love.

Placing yourself as a spectator on a public scene can sometimes make a scene. What do you do when you are caught looking? Be sensitive. If your subject seems uncomfortable, irritated or alarmed: stop. Draw unto others as you would have them draw unto you. If at all possible, apologize for taking them off-guard and explain that you’re an artist practicing your art, and show them your work. You might be surprised at how understanding and supportive people can be. Artist Chapman Hamborg gives his drawings to his subjects, using the exercise simply to bless people in passing.

All the world’s a stage, and all the men and women merely players. William Shakespeare

There’s a lot of movement going on when capturing un-staged subjects. When dealing with constant changes I make a helpful shift in mindset: my objective changes from capturing my subject exactly to instead capturing the nature of my subject. The challenges of secret sketching (movement, limited time, discomfort) can push us towards artistic betterment and expression. Like Degas’ drawings which showed us the rarely seen view of the backstage life of ballerinas (image below), drawing people who make cameos in our day-to-day life can bring people a view into our “backstage” life; the hustle & bustle, the beautiful mess of it all.

What do you need to be an undercover artist? Guts! As for my favorite materials right now: a small tan pad of paper, a box of pencils, an eraser, sharpener, and a white charcoal pencil. You can get super streamlined with a spy-worthy kit of a moleskin pad of paper and a multicolor pen. Anyway, you do it, give it a try if you haven’t already.

Are you already an “undercover artist”? Or do you plan to be? I would love to hear your thoughts. Please leave a comment below.

Artist, DNY Instructor and Author
I love painting faces, flesh, and fabric. The more tactile I can make a painting feel, the more I’m satisfied with it! I feel blessed to make art every day and look forward to the next day to continue my projects. Traveling to teach workshops is also something I can’t believe I get to do.
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Kelly Foss Author
I love painting faces, flesh, and fabric. The more tactile I can make a painting feel, the more I’m satisfied with it! I feel blessed to make art every day and look forward to the next day to continue my projects. Traveling to teach workshops is also something I can’t believe I get to do.
2 Comments
  1. Great article. I have never done this myself, but my friend and I were drawn by an incognito artist in my senior year of college. We were in a coffee shop in downtown Chicago, the near north side. The coffee shop was a Seattle’s best circa 2002 (I miss that coffee shop…”there are places I remember…some have changed some have gone…some forever not for better”), and we were talking about our plans after college (the plans of mice and men) and he drew us doing these activities. He then “gave” me his sketch for a small donation of a few bucks. I still have the sketch and I am glad for it. It helps me relieve those times.

    1. That is awesome! What a wonderful thing to have bought that drawing to be able to relive those memories at a glance (a time capsule on paper). 🙂 Thanks for commenting, Frank. I love hearing stories like this.

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