CHICAGO -- Jacob Ryan Reno, long and boyish, wearing the kind of blue smock you imagine a painter would wear in a cartoon about a painter, is not good at his job. He draws and has become pretty popular in Chicago for those drawings. Yet … he’s so bad at it. So bad he inspires a perverse confidence in that lack of talent, partly because he warns everyone with a sheepish smile that he’s not very good. When I asked a woman in Logan Square why she was waiting for Reno to draw her portrait, despite knowing his skills were questionable, she replied, with irony: “He must be talented if there’s a line.”

She added, “I mean, what if he becomes famous someday?”

Then she mentioned, even more straight-faced this time, that she was an “art enthusiast.”

And Reno, for sure, is an artist, a young Chicago one, just 26, and all that entails, doing a little this, a little that, living in Logan Square. Some acting, some performance art, a bit of stand-up, waiting tables. He radiates a rangy energy. He’s thrilled to be creating anything. Maybe you know the type.

Three months ago, he had an idea that he would take a folding table to the Sunday farmers market in Logan Square and draw portraits, for $5 a pop. But with a twist. He announced his services with a handprinted sign:“Terrible Portraits. 5 Terrible Minutes.”

Since that Sunday in May, he’s drawn 600 or so portraits, and become so popular via social media that he’s been getting requests from a number of famous faces. Questlove wants one. The day I watched him work, he cut off the line for portraits earlier than usual because he was due at the Salt Shed that afternoon, having been asked by Wilco to draw the band before their show that night. He’s just started getting hired to draw his miserable portraits at weddings and birthday parties.

“The funny thing is, since starting, I’m not getting better,” he told me.

No? I asked, wondering what his art looked like before it was merely terrible.

“No,” he said, “I think I’m actually getting worse.”

Fair enough. His repertoire, so far, is limited to faces and he’s lousy at it. His heads resemble supermarket hams. His eyes look hypnotized or insane. He sketches hair with the sharp, slicing strokes a toddler might use to draw a haystack. His mustaches could be train tracks. His noses all look the same, like wine bottles. His mouths are bananas, as in the food. Like other visual artists, while he’s working, he looks up to see what’s in front of him, returns to his palette, looks up again — but I started to wonder if all that looking up was performative. I watched two very different friends get a joint portrait and after sitting in front of Reno for five minutes, the results were almost identical. Two long heads. Same black hair. Same sunglasses. They looked exactly like Oasis.

Celia Simon, one of those women, studied herself on the heavy poster stock that Reno uses for his portraits. She coughed out a laugh, then, on second thought, decided she loved it. “No … god, it’s actually perfect,” she said. “I mean, I’m going to take this to my doctor’s office. I keep telling them my nose looks crooked and they’re just not getting it.”

Jacob Ryan Reno, a native of Redondo Beach, California, arrived in Chicago a decade ago, for college. He attended DePaul University, studied screenwriting. The origin of “Terrible Portraits,” a story he’s repeated many times while small-talking with whomever he’s drawing, is that he and a friend from college were at a house party and decided to draw each other for fun. His friend was horrified at what Reno came up with. She asked: “Is this how you see me?” She was sort of kidding.

That was seven years ago.

Skip ahead to last spring, and Reno was slogging through a brand strategist that he decided “did not align” with his values. He also didn’t like the 9-to-5 lifestyle. So he quit.

About that time, he came across the original drawing from that house party and, on a whim, decided to re-create “Terrible Portraits” in the wild, partly for the money, partly because he likes to talk to strangers, partly because it seemed fun.

“I was there first day,” said Al Smart, his partner, themselves a sometime actor, sometime artist, sometime florist. “He was nervous. He was, like, ‘Will people get offended? This could just be stupid.’ But right away, that’s not what happened. Right away, I think we kind of realized, this is a service, this is an experience. Without getting too heavy, we talked about art and how good art, no matter the medium, is about you creating for someone who is there with you — and ideally, the artist is getting just as much enjoyment from it.”

Since that first attempt, a scene has sprung up every Sunday around Reno.

He sets pens in front of him. He tidies a thick sheet of paper. He waits. The other day, when I watched him make portraits — for almost three and a half hours, only taking a second to eat an empanada that had long gone cold — he was barely seated when his first client approached. Other than appearing across the street from the Logan Square Farmers Market on weekends, he pops up around Chicago during the week, at festivals, at parks. He doesn’t announce where he is going on Instagram but has considered advertising his services by posting terrible self-portraits on Milwaukee Avenue that ask:“Have you seen this man?” He likes the surprise. At The 606 trail, a man stopped and asked him what he was raising money for. Reno said, “I don’t know. My vibe?”

As he draws, clusters of hopeful muses hover nearby, waiting for their chance. They mutter that he looks like John Mulaney, which he definitely does. Reno places a speaker on the table and plays bebop. He wears a cravat around his neck, just like you know, artists.

Friends Abbey Londa, from left, Becca Weisz, Lauren Smith and Francesca Sands laugh as they look at the portrait Jacob Ryan Reno drew of them in Logan Square Park on Aug. 10, 2025. Reno draws "terrible" portraits of people for $5. (Eileen T. Meslar/Chicago Tribune) No one, faced with their portraits, has gotten mad yet.

A 10-year-old boy, seeing his portrait, did scream, “ ARGHHHH!” And Reno screamed back, “ THE HORROR!” But mostly his clients make small talk about relationships and bike routes and apartments. They leave sly comments on the results: “Like looking in a mirror!” “It captures my beauty!” Some said they liked the low stakes. Some said they could never afford, let alone show the patience, to sit for a traditional artist portrait.

“Did you go to art school?” a man asked, sincerely.

Reno winced and said, “ NOOOOOOOOOOO.”

Still, a fair question. This could be a gag. Some wonder if he’s secretly good. Another customer mentions to Reno what he’s doing feels reminiscent of outsider art, or so-called naive art, the kind of self-trained, sometimes childlike work that’s an art-world niche, filling places such as the Intuit Art Museum in West Town and the Art Preserve of Sheboygan, Wisconsin. Reno’s portraits are never flattering, yet they offer a consistent vision. Plus, like other outsider artists — a term Reno only recently heard for the first time — he says he does this because, well, he just does it, has never thought about getting sick of it, hoping to be considered a professional artist or evolving as an artist.

The closest Reno gets to an artist statement is when he says that anything less than spontaneous about “Terrible Portraits” would feel “antithetical to everything I’m doing with this. I’m a big believer in art everywhere, but I also think, in an age of AI-generated art and ChatGPT, I worry about if we’re losing the art of communication, face to face.”

He fears that a “weird tension” could develop between him and some of the people he draws, an expectation for him to draw them, as promised, as poorly as possible. He doesn’t think about this as a performance.

“I am not playing a character. I actually am trying to draw people well. I hope when people sit across from me that they know that. I hope they know that I really am trying as hard as I can, but it will probably be terrible.”

A couple from Lincoln Park, Abby Auwaerter and Will Morris, sat across from Reno. “You know, this is actually the second time we’ve sat for a portrait,” Auwaerter said. The first portrait was in Key West, and it was done by the sort of traditional sidewalk sketch artist found in tourist towns.

“But that one,” she continued dryly, “was not advertised as terrible.”

“Yeah,” added Morris, “I mean, at least you’re transparent.”

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