Terrible Chicago artist draws terrible Chicago portraits. And finds a niche

He became pretty popular in Chicago for his 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, even more straight-faced, she mentioned she is an “art enthusiast.”

Creative creator

The 26-year-old Reno lives in Logan Square. He does some acting, performance art and stand-up, and waits tables. He radiates a rangy energy, thrilled to be creating anything.

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 gets requests from a number of famous faces.

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, as Wilco asked him to draw the band before a show that night. He 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.”

At work

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.

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.”

How it started

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.

Last spring, Reno was slogging through a brand strategist job 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.”

Every Sunday, Reno sets pens in front of him. He tidies a thick sheet of paper. He waits.

When I watched him make portraits — for almost three and a half hours, only taking a moment to eat an empanada that had long gone cold — he was barely seated when his first client approached.

Air of mystique

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 considered advertising his services by posting terrible self-portraits on Milwaukee Avenue that ask: “Have you seen this man?”

As he draws, clusters of hopeful muses hover nearby, waiting for their chance. They mutter that he looks like comedian 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.

A 10-year-old boy, seeing his portrait, screamed, “ ARGHHHH!” 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!”

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

Reno winced and said, “ NOOOOOOOOOOO.”

Some wonder if he’s secretly good.

Consistent vision

Another customer mentions to Reno that 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. He's 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," he said, referring to generative artificial intelligence tools, "I worry about if we’re losing the art of communication, face to face.”