For $5, this man will draw a terrible portrait of you

You can find Jacob Ryan Reno at his neighborhood farmers market on Sundays. He doesn’t sell fresh produce or flowers. Instead, he offers portraits — bad ones.

Dressed in a blue painter’s coat and a cravat, Reno sits behind a foldable table with a painted sign that reads: “TERRIBLE PORTRAITS, $5, 5 TERRIBLE MINUTES.”

Jazz music plays in the background. One chair is for him, and the other is for his muse.

Every week, people line up for their turn to take home a hand-drawn portrait that might look like them. Or it might not. Since becoming a self-proclaimed portrait artist in May, Reno, 26, has drawn more than 500 people. His sketches are disproportionate, sometimes awkward and usually unflattering — yet charming.

“I think people are just looking for something fun and something that doesn’t take itself too seriously,” said Reno, who lives in Chicago’s Logan Square neighborhood. “Even though I do take it incredibly seriously.”

Reno first tried his hand at portraiture at a house party in 2018. Reno, then a student at DePaul University, and a friend thought it would be entertaining to sketch each other in the middle of the party. They set a timer for five minutes.

“She turns hers around for me and it was pretty good, and then I turn mine around for her and she was visibly upset,” Reno said.

They both broke out in uncontrollable laughter. Reno realized he might have unearthed a hidden talent.

“To be a terrible portraitist, I feel like there’s really something there,” he said.

Still, he did not pursue portraiture right away. It wasn’t until this past spring, when he came across a photo of his original drawing from the party, that he considered turning the joke into something real. Around the same time, he quit his media job that “didn’t align with my values” and bought a piece of poster board and some blue acrylic paint to advertise his services.

He set up shop for the first time on May 18 at the Logan Square Farmers Market.

“I was like, if I draw four people, I’ll be happy,” Reno said. “This is something I thought would make people smile and laugh, and that’s why I began doing it.”

To his delight, a steady stream of strangers stopped by for their “five terrible minutes” with Reno. The reception was overwhelmingly positive.

“I care a lot about what I’m doing, but overall, it’s just so fun,” Reno said. “I love the opportunity to chat. … I do not view it as work.”

Indeed, Reno doesn’t just draw — he performs. He chats with his subjects and tries to get to know them. He sets a timer for five minutes, but he almost always goes over.

“I want to make it as comfortable and as inviting of an experience as I possibly can,” he said.

Reno’s portrait project has quickly evolved into more than a hobby, and he got a boost when his experiment was covered by local news site Block Club Chicago. He’s been hired for weddings, housewarmings and birthday parties. In addition to his regular stand at the Sunday farmers market, Reno will often pop up unannounced at a local bar or park.

“It’s such a joy, because he doesn’t tell anyone where he’s going to show up around the city,” said Victoria Lonergan, 28.

On July 20, she and her roommate went to a bar and saw him drawing portraits on the patio. Lonergan used to work with Reno at an advertising agency, so she stopped by his stand to see what he was up to. Reno offered to draw her and her roommate.

“I tried to hide my eyes from the horror of what he was creating of my face,” Lonergan said. “When he flipped it around, it was just so funny. I think I laughed for five minutes.”

Lonergan framed the drawing — intentionally crooked — and hung it on the wall of her living room.

Reno is not the only person charging for terrible portraits. A Brooklyn street artist has made waves selling $5 portraits he makes in 60 seconds, and a U.K. accountant went viral for his “absolutely horrendous” commissioned paintings.

“There are other people who do things like this, but I had not come across them before I started doing this,” said Reno, who also performs as an actor, DJ and stand-up comedian, and works at a local restaurant. “It’s so rewarding to have the idea resonate.”

He said he understands why his rough renderings have struck a chord with people: They’re approachable, disarming and comical.

“It’s a bit of an absurd thing,” he said. “What really gets me is when people walk by and just snicker to themselves. I think there needs to be more levity.”

While Reno’s drawings are unpolished by design, he insists he tries to make each one good. He uses a variety of art pens and draws on white cardstock.

“The truth is, I’m trying as hard as I can on every portrait I do,” he said. “I really am trying my best.”

Rather than aiming to represent someone’s appearance, Reno strives to capture their spirit.

“I’m really trying to take somebody in and capture someone’s essence,” he said. “I would hope that when people sit in the chair, they do know there is a lot of care that goes into each piece.”

When he first started, he worried about hurting people’s feelings.

“That is the last thing that I ever want to do,” he said.

So far, “nobody has been upset,” said Reno, who documents his art on Instagram. “I think anyone who is consenting to the experience has at least some sense of humor, and they know what they’re getting themselves into.”

Christian Borkey, who got her portrait done with her piano partner in mid-July, agreed.

“I think it is absolutely hilarious that he is doing terrible artwork,” she said, noting that a bunch of people gathered while Reno drew her in a local park. “I laughed my head off when he turned it around.”

“Not only did I laugh,” Borkey said, “the whole group laughed.”

“It’s one of those things where people can sense the good energy, and they’re drawn to it,” she added.

Reno said what he loves most about his portrait project is that it allows him to mingle with people in his community and make them chuckle.

“I’ve met a lot of people through it, which is incredible,” he said.

Ultimately, Reno said, it’s not really about the portraits at all. In a world that is increasingly digital, he believes his artwork offers a rare chance to slow down and connect.

“What I try to provide is just an incredibly human experience,” he said.