A Kenwood basement-turned-gallery will highlight the works of long-time South Side painter Donnie Carter next month. The show, titled “Signs of Life,” opens Feb. 1 at Studio Bootsie and will run through the month.
Carter is an 87-year-old sign painter, cartoonist and muralist. He’s lived in Chicago since 1955, and his work can be seen at several banks and grocery stores in the area, as well as in the DuSable Black History Museum and Education Center. The exhibition will primarily showcase Carter’s private work — paintings that have lived in his apartment for years, though some of his sign-lettering will also be on display.
That’s the kind of art Dawn Brennan said she wants Studio Bootsie to bring into public view.
“I felt like Donnie was interesting partly because of his life story, but also because he makes these paintings for himself, they are untrained but they have a lot of appeal and I think they are absolutely worth showing,” said Brennan, who opened the studio in July.
Carter was born in 1939 in the small town of Sunflower, Mississippi, where he worked on cotton plantations from a young age.
“When I lived in the country, I was picking cotton during the day, and painting pictures all night,” Carter told the Herald. “When we were working for this one guy, he told me, ‘stay here, I want you to paint the numbers on the cotton sacks.’ At that time I was around twelve years old. It was just natural with me.”
He said that although he felt like a “Chicago boy living in the South,” he takes pride in his roots. Carter sees his experience working in the fields as deeply formative to his artistic development.
“I was always good at art, but picking cotton taught me how to master a technique,” said Carter, who, to this day, lists “master cotton picker” as a skill on his resume.
The oldest piece in the exhibition, a self-portrait painted at age 13, offers an intimate look into this time in the artist’s life.
A self-portrait of Donnie Carter, 1952.
He moved to Chicago just a few years after painting that self-portrait, and made a living painting signs for grocery stores and banks. When he wasn’t sign painting, Carter spent his free time sketching musicians in jazz clubs on the South Side (among them Sam “bepop” Thomas), many of whom were his close friends. From these sketches, he would create larger paintings, some of which will be on display at the exhibition.
“I was never a sculptor or anything, so one of the reasons I painted musicians was to get a chance to practice painting their hands. When you paint a trumpet player, you have to paint the hands right,” Carter said, before raising his hands to his face and performing an impromptu mouth-trumpet solo.
Carter’s philosophy for art-making is straightforward. If something piques his interest, he paints it, whether it’s a picture in a magazine, or a scene conjured up in his own mind. It is for this reason that his work doesn’t adhere to one specific style or form, a fact most evident in a piece he titled “First Day of School,” a pointillism-style painting that stands out from the rest of the work on display.
“I decided to do something different. I used the back of the brush, no brush strokes, just dots. For two hours every night I dipped the back of the brush in paint and made dots on the canvas,” said Carter, calling the painting his “masterpiece.”

“First Day of School” by Donnie Carter, 2024.
Though varied in style, all of his paintings carry a sense of ease, something that the artist himself exudes. Though Carter spoke much about problems of class and racial inequality, violence and injustice, he said his art-making is not about political or social statements. Instead, Carter’s work, whether it’s an impressionist painting or a billboard, comes from that same part of himself that motivated him to make his own toys at 7 years old — an innate drive to create.
“Signs of Life” will have an opening reception on Feb. 1 from 3 p.m. to 6 p.m. at Studio Bootsie, 4335 S. Lake Park Ave. Studio Bootsie is open to the public on Sundays from 2 p.m. to 5 p.m. or by appointment.
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