Why people in Chicago are waiting hours in line to buy this man’s ‘terrible’ $5 portraits
“I am absolutely bewildered by the reception. I’m really astounded by it.”
Jacob Ryan Reno is creating something special in Chicago.
In a world increasingly dominated by AI-generated perfection and filtered faces, Jacob Ryan Reno's art feels radical. The 26-year-old hit the delight jackpot, drawing large crowds to his "Terrible Art" stand, where he embraces his artistic inadequacy and, therefore, transcends into a viral sensation and profound joy.
There's no catch—he's genuinely bad at portraiture. And people are lining up for hours to pay him for it.
Every Sunday at Logan Square Farmers Market in Chicago, you'll find Reno sitting next to a small, blue folding table. Leaning against it is an extensive hand-painted sign reading: "TERRIBLE PORTRAITS, $5."
Then, beneath in smaller handwriting: "5 TERRIBLE MINUTES."
It's quickly clear that something extraordinary is taking place.
How does one begin to describe Reno's self-proclaimed "terrible" drawings? Is it performance art? A subversive act? Simply a man proudly owning his mediocre (at best) portrait skills?
Armed with nothing more than art pens, poster board, and an unwavering commitment to never improving his craft, Reno charges $5 for five minutes of what he calls "an incredibly human experience." His portraits feature elongated heads, jagged hair resembling haystacks, noses that look like wine bottles, and mouths drawn like bananas. Yet people line up eagerly, sometimes waiting hours for their turn to be immortalized in wonderfully wonky form.
Reno's sketches are crude, disproportionate, and "sometimes awkward." Eyes bulge, pupils are dilated. Hair often seems like a messy afterthought. Teeth are drawn uniformly, like a pack of pearly, trident gum smiling up at you.
"I am, indeed, a terrible portraitist," the Chicago artist told As It Happens guest host Rebecca Zandbergen. "I have no intention of getting better. Actually, I intend to get worse, to be honest with you."
From house party disaster to artistic philosophy
Reno's journey into terrible portraiture began seven years ago at a DePaul University house party, where he studied screenwriting. What started as a simple drawing exercise with a friend turned into a pivotal moment for Reno when he produced a horrifyingly inaccurate portrait of his friend, and he looked "genuinely disappointed," asking, "Is this how you see me?" The memory of that mutual laughter stayed with Reno through various career attempts, including a stint as a brand strategist that he left because it "didn't align with my values."
Later, the rediscovery of that original terrible portrait last spring sparked an epiphany. "Something is interesting about this," Reno recalled thinking. Over time, Reno's whimsical experiment has evolved into a philosophical statement about authenticity, human connection, and the value of imperfection in our increasingly polished digital world.
"I fully acknowledge that I am not a skilled portrait artist," Reno told CBC Radio with characteristic honesty. "I have no desire to improve. In fact, I plan to decline further, to be frank." This commitment to deliberate mediocrity isn't laziness—it's artistic rebellion against the pressure for constant self-improvement and digital perfection.
Performance art meets community connection
It's important to understand that the portrait itself is only half the experience. Setting up his folding table with jazz music playing in the background, Reno transforms each sitting into a performance piece. He engages clients in genuine conversation, asking about their lives, relationships, and dreams while his pen captures their essence in wonderfully distorted form.
"I want to make it as comfortable and as inviting an experience as I possibly can," Reno explained. Here's a little secret: although the timer may say five minutes, he almost always goes over, prioritizing the human connection over efficiency. This approach has created something remarkable: a community gathering point where strangers become friends through shared laughter at their own terrible portraits.
One particularly touching moment occurred during his second week, when a nervous 10-year-old boy approached with $5 from his father. Despite Reno's warning that the result might not be appealing, both artist and subject burst into laughter when the portrait was revealed. "We laughed for about two and a half minutes," Reno recalled. "That moment was really a clear indication that this is something genuine and positive."
Reno's viral success… and celebrity commissions
Since launching his farmers market booth in May, Reno has completed approximately 600 portraits and gained massive social media attention. His Instagram account @terrible.portraits has attracted followers worldwide, leading to features on major news outlets including the Washington Post, Chicago Tribune, and CBC Radio. The phenomenon has even reached celebrity circles—Questlove has reportedly requested a commission, and the Chicago band Wilco invited Reno to sketch them before their performance at the Salt Shed.
The viral nature of Reno's work speaks to something more profound than mere novelty. In an era of AI-generated art and Instagram filters, his deliberately imperfect portraits offer a refreshing antidote to digital perfection. "I strongly believe in art being everywhere," Reno said, "but I also worry that in an era of AI-generated art and ChatGPT, we might be losing the art of face-to-face communication."
This philosophy has resonated with clients who find the experience liberating. Victoria Lonergan, a former colleague who encountered Reno at a bar, described watching him work as both horrifying and hilarious. "When he flipped it around, it was just so funny. I think I laughed for five minutes," she said, before framing the portrait and hanging it in her living room.
The "terrible" empire is growing
Reno's success has naturally led to expansion beyond the farmers' market. He now appears at weddings, birthday parties, and private events, bringing his unique brand of artistic mediocrity to celebrations across Chicago. His dream gigs include bar mitzvahs and quinceañeras, events where his ability to create joy through shared laughter would be especially appreciated.
The wedding market represents a fascinating evolution of his work. While traditional wedding photography seeks to capture perfect moments, Reno offers couples and their guests something entirely different: portraits that are so deliberately imperfect they become ideal conversation pieces and icebreakers. As one couple from Lincoln Park noted after collecting not-so-flattering portraits from both Reno and a traditional Key West street artist, "at least you're upfront about it."
Perhaps most remarkably, Reno has created a genuine community around his work. Regular market-goers know to expect him on Sundays, and his impromptu appearances around Chicago generate excitement among followers who never know where he'll pop up next. The Reddit Chicago community has embraced him enthusiastically, with posts about his work generating hundreds of upvotes and comments from satisfied customers.
The success of "Terrible Portraits" suggests a broader appetite for creative experiences that prioritize human connection over technical excellence. While AI can now generate flawless portraits in seconds, Reno offers something artificial intelligence cannot: genuine human interaction, shared laughter, and the beautiful imperfection that makes us most human.
As Reno continues his terrible artistic journey, refusing to improve while paradoxically perfecting the art of joyful failure, he reminds us that sometimes the most beautiful thing we can create is a moment of genuine human connection—even if the portrait looks nothing like the person sitting across from us.
Just when you think you know everything about your job…