
Child’s Play: The Paintings of Kayla Mahaffey
In 2019, Kayla Mahaffey reached a turning point with her art. The Chicago-based artist had a solo show at Line Dot Editions in April of that year. Titled Off to the Races, the series of paintings centered around children ready to hit the road. Some sat with their growing legs crouched in tiny cars or stretched to move bike pedals. Their heads were protected by helmets of varying shapes and sizes. All were surrounded by 2-D characters, some recognizable from cartoons and comics. The kids express a range of emotions. Some are confident despite obvious mishaps on the road. Others are nervous, excited, frustrated, or hopeful. Some might be a mix of all that.
In “Stranded,” a four- by five-foot acrylic on wood painting, two children have been waylaid. It’s one of Mahaffey’s personal favorites from the show. One child fixes a blown tire. The other, whose legs are covered in tiny bandages, sits on the ground next to a wrench. “Their faces really show they’re not having it,” says Mahaffey on a recent phone call. Surrounding them is a pastel-colored fantasy with big flowers and a dapper koala bear. They might be frustrated by their current situation, but the world surrounding them is still magical. They haven’t lost their imagination.
“That was probably the show where I felt like I knew what I wanted to do, what I wanted to convey,” Mahaffey recalls. “I wanted it to have a feeling of victory, a feeling of resilience, feelings of never giving up.”
Mahaffey’s calling card is her ability to seamlessly merge the detailed realism of portraiture with elements influenced by—and often directly referencing—animation and comics art. It’s a careful balancing act of illustration and painting techniques at which she excels and it’s made Mahaffey an in-demand artist in recent years. When we spoke, she was preparing to start work on a solo show set to open at Thinkspace later in 2021, her second at the Los Angeles gallery in two years.
But it was at that 2019 Line Dot exhibition when Mahaffey began to see the results of her years of experimentation. “That was the first one where I really successfully put the two worlds together and you can feel it,” she says. “You can visually see that it was serving a purpose of what it was supposed to do and the composition really worked in what it was trying to say.”
The 2-D is supposed to represent the whimsy, wonder, imagination that we all possess…”
On a very basic level, Mahaffey’s style is an answer to the question, what kind of art should she make? As a child, she wanted to be an illustrator. Children’s book art has been a big inspiration. She was—and still is—a fan of cartoons and comic books. Dr. Seuss books, vintage Disney, Scooby-Doo, The Jetsons, and Hellboy are all part of her pool of influences. During her two years at Chicago’s American Academy of Art, she struggled with deciding on a major. Should she go for illustration or fine art? “I didn’t really want to choose,” she says of the two disciplines. “I started trying to figure out a way to meld them, merge them together, where they can kind of have a little bit of both.”
Early on, Mahaffey’s work fit solidly in the realm of fantasy art. She illustrated mermaids and warriors and captured the sort of pastoral settings that are reminiscent of tales like The Lord of the Rings. With time, she pursued another visual language. Mahaffey leaned into her pop art influences and switched from primarily relying on watercolor to painting with acrylics. Fantasy has since become a deeper theme connecting her paintings.
“The 2-D is supposed to represent the whimsy, wonder, and imagination that we all possess,” says Mahaffey. The portraits and heavily rendered portions of the paintings root the images in reality. “We all have that side of us that’s more fantasy, more whimsy, more imagination,” says Mahaffey, “but in our daily lives, we don’t necessarily show it.”
Earlier in her career, Mahaffey painted a lot of adults, particularly seniors. But she began to think back on her general conversations with older people and the regrets that were expressed, how they might have wished they could return to their youth and perhaps do things differently. “There’s that thing about getting old and having regrets,” she says. However, she adds, “you could still live somewhat like a kid, but you don’t necessarily have to be a kid.”
While the paintings largely focus on children now, they aren’t literally about children. “Even though the figure represents a kid, they don’t necessarily have to be an actual kid, more like the kid that’s inside of you,” she says.
Mahaffey notes that people might think of youth as something they can’t get back. She has a different attitude. “Just by living, in a sense, you will feel younger,” she says. “You won’t feel so much regret if you start enjoying the things that you do instead of taking everything a little bit too seriously.”
When Mahaffey references pop culture in her work, she draws from different eras. She might include nods to Golden Age U.S. cartoons, classic anime or eight-bit video games. It might also include bits of twenty-first century pop culture. This broad span of visual cues allows her messages to speak to multiple generations of viewers. The kids in the paintings aren’t necessarily the children of the 2020s. They might be Boomers or Gen X, Millennials, or Gen Z.
I wanted it to have a feeling of victory, a feeling of resilience, feelings of never giving up.”
Sometimes, Mahaffey’s pieces are influenced by personal situations. In “Wear and Tear”—from her 2020 Thinkspace solo show Deconstructed—she depicts the face of a young girl split in half by a group of cartoon characters who appear to be climbing out of her head. On one side, the girl’s mouth forms a soft smile. On the other side, her expression is pensive as two tears drip towards her cheekbone.
Mahaffey says that, at the time of making this painting, she struggled with balancing “life in the art world” and wanted the piece to reflect that. “I wanted to go with what it felt to be pulled in one direction and another direction,” Mahaffey explains, “but, at the same time, having to hide what I was truly feeling inside, without letting it show on the outside.”
“Wear and Tear” was a more complicated piece to paint. “The hardest part was trying to paint realistic skin tones around the 2-D and then trying to go back in and trying to fix,” says Mahaffey, noting that she would work right to the edge of the figures, working to ensure that the paints didn’t bleed into each other. “It was definitely easier to draw than it was to actually paint, when it came to doing flesh tone right next to the 2-D figures inside the face,” she says.
“Wear and Tear” is a beautiful example of Mahaffey’s knack for merging two very different stylistic choices. In her portraits, she captures the depth of skin tones and hair colors, while the imaginative elements maintain the flatness associated with animation art. She says that, often, it’s those 2-D elements that are more difficult to paint. “I’ll have to do four or five layers of the same color just to get white gloves,” she says. “Three coats for the white gloves and then wait until the next day, when it’s dry, and then do some more coats and then keep doing it over and over again just to get that one white to be very stark.”
Mahaffey often works fast. “I’m trying to slow down—finally,” she says. “With my first solo show, it was way worse. I didn’t know. I’m thinking other people are fast because they have so much more work. I would paint a straight marathon. I would paint a painting each day, which sounds crazy now that I think about it.”
Still, maybe because of her speed, she’s been able to respond to current events with her art. In early June of 2020, she posted a piece on Instagram made only a day or two earlier called “Silence Must Be Heard,” reflecting on the Black Lives Matter movement. In the painting, a boy moves his finger towards his mouth, gesturing for quiet. Amongst the characters surrounding him is the Shy Guy from the Super Mario Bros. video game series. Mahaffey says that the piece is about finding ways to speak up and giving “voice to people who don’t usually feel like speaking up or they feel like they won’t be heard, if they speak up.”
Later in the year, Mahaffey made another powerful piece encouraging Americans to vote, as part of the When We All Vote campaign. Here, a young girl looks towards the sky. Her hair, styled in two braids, flies behind her, and the sun shines against her face as she smiles. In her expression, there is a mix of joy, pride, and hope. Mahaffey keeps the 2-D elements to a minimum with details like an American flag, a ballot box, a few Mickey Mouse-style hands, and three airplanes. The word “Vote” is written in the sky. “I wanted to keep it straight to the point,” she says. “And I want it to be something that people can see and not only could they feel happy about it, but they could feel hopeful.”
Sometimes, Mahaffey works with models, either live or by photograph. Other times, they are people emerging from her mind, “a mashup of faces I can remember,” as she says. “When I don’t use a model, of course I do experiment a little bit more with coloring certain things or adding more elements into it,” she says. “With having an actual model, sometimes it might stay too close to the picture—where I’m just trying to paint them—so I can only stray away from that a little bit.”
One thing that carries through all her pieces, though, is her deftness in conveying multiple messages through faces. Mahaffey’s people say a lot—about dreams and goals, about frustration and persistence, about complicated feelings—without ever speaking. It’s the work of someone who seemingly has studied people for years. “Yeah, I’m a people-watcher,” she confesses with a laugh. “I feel bad, but I do people-watch a lot.”
She adds, “Maybe, I’m just checking out people’s expressions.”*
This article first appeared in Hi-Fructose Issue 58, which is sold out. Support what we do and get our latest print issue with a subscription here.
Ukraine-born, Paris-based artist Nikolay Tolmachev crafts provocative watercolor paintings showcasing a knack for elegance and wry humor. The artist's practice also delves in illustration, recently providing work for a release of the classic narrative poem "Kateryna" by Taras Shevchenko.


