Chicago Street Artist Leon Thoughtsky Combines Familiar Signs and Provocative Words


You think it, he paints it.

That’s essentially the premise of a local street artist’s work. He aims to paint what everyone’s thinking, but isn’t saying.

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Leon Thoughtsky takes sardonic quips and reflections and mixes them with the painted signs often seen advertising grocery store produce.

By sardonic quips, he means buzzwords that have the potential to get a rise out of people. But that isn’t the intent of Leon Thoughstky’s work.

“I reflect on the behavior that I see,” Leon Thoughtsky says. “Then I abstract the circumstance out of it. Then it almost gets to a logic that when you express, it becomes very clear, and I think that when people see it, it gives them pause. Then they can reflect on their own actions and behavior.”

In other words, he’s saying what everyone’s thinking, but isn’t saying.

“It has a sentiment of irony that might be lost on some people,” he says. “But I think the style is so absurd that people generally know right away that something is not right in the piece. It will at least give cause for reflection.”

The purpose of a dialogue is to change the other person’s mind.

If I can’t find an enemy, I just expand the criteria.

Opium is the religion of the masses.

These are some of the phrases that came to Thoughsky’s mind during lockdown. When it came time to go outside again, he hit the streets with his sardonic quips.

“I want people to be a little unnerved. Just from my perspective, people’s behaviors and actions have been chaotic. It’s sort of been challenging to watch,” he said.  

While the artist behind Leon Thoughtsky intends to remain a mystery, it doesn’t mean he’s absolved from his alter artist ego’s encouragement for self-reflection.

“He is a person that I guess is loud and bold that's not who I am – quiet and introspective. It’s nice to hide behind that alter identity and let Leon Thoughtsky go,” Thoughtsky says.

Chicago street artist Leon Thoughtsky takes sardonic quips and mixes them with the painted signs often seen advertising grocery store produce. (WTTW News) Chicago street artist Leon Thoughtsky takes sardonic quips and mixes them with the painted signs often seen advertising grocery store produce. (WTTW News)

He says the end goal of his work is to encourage those who view it to have some mindfulness about how they're acting.

“It’s also … a lot of it isn’t for other people. But it is also for me to work on my own self and own behavior. I do try to take these to heart,” he said. “I don’t think anyone can get out of these or get out of these ideas or concepts. But it’s good to be aware of them and to check yourself. How are you affecting others, and just be more aware.”

This end goal has proven to be true. Thoughtsky says he has fans to the point where they’re regularly taking his street art down to start collections at home.

“People have reached out and said this is something I didn't even know about myself, but when I saw it, it correlated with something that I do. So now I’m rethinking how I think and see the world,” he explained.

While the purpose of Thoughtsky’s work is to encourage self-reflection and growth, it’s also meant to serve as a reminder.

“It’s better for people’s ideas and opinions to be out in the light, even if they're bad. We have to take them up and talk about them,” he said. “The Trump phenomenon was a repressed cultural phenomenon. Not to get political. People’s minds aren’t going to be changed in silence. You need dialogue.”

Leon Thoughtsky says he has no plans to ever reveal his identity or really take his work beyond the street. You can currently see Thoughtsky’s work at these locations:

  • 4598 N. Cicero Ave.
  • 3190 N. Milwaukee Ave.
  • 2815 W. Armitage Ave.
  • 1995 N. California Ave.
  • 1630 N. California Ave.
  • 1910 N. Milwaukee Ave.
  • 1230 W. Randolph St.
  • 305 N. Morgan St.
  • 64 E. Randolph St.
  • 172 N. Michigan Ave.
  • 667 N. Wabash Ave. (Northeast corner)
  • 644 N. Clark St.

They won’t be featured in an exhibit anytime soon.

Follow Angel Idowu on Twitter: @angelidowu3


Angel Idowu is the JCS Fund of the DuPage Foundation Arts Correspondent.


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