The $5 Portrait That Made Chicago Stop: A Self-Proclaimed Terrible Artist Draws Crowds by Embracing Imperfection
In a world chasing AI-perfect faces, Chicago’s Jacob Ryan Reno is offering something radically different. At Logan Square Farmers Market, a blue folding table bears the banner: TERRIBLE PORTRAITS, $5, and five minutes of art. There’s no catch — he insists he’s genuinely bad at portraiture, and yet crowds line up for hours to pay for it, turning a simple sketch into a moment of human connection. Reno’s “Terrible Portraits” have become a phenomenon by embracing imperfection as a counterpoint to digital polish. It’s not just a sale; it’s a statement about authenticity in a world increasingly filtered and perfected.
In This Article:
Who is Jacob Ryan Reno and what is Terrible Portraits?
Reno, 26, sits beside a small blue folding table every Sunday at Logan Square Farmers Market. A hand-painted sign declares: “TERRIBLE PORTRAITS, $5.” Beneath it, in smaller script: “5 TERRIBLE MINUTES.” The setup signals something extraordinary is happening. Reno calls himself a terrible portraitist. He’s studied screenwriting at DePaul University and once worked as a brand strategist, but eight years later he’s chosen a life of deliberate mediocrity as performance art. “I am, indeed, a terrible portraitist,” he told As It Happens host Rebecca Zandbergen. “I have no intention of getting better. Actually, I intend to get worse, to be honest with you.” This is not laziness; it’s a rebellion against the pressure to improve and to chase digital perfection.
The Performance of Mediocrity: People Connect Through the Process
Reno’s portrait sessions are a living performance. He uses art pens and poster board, with jazz playing in the background, turning each sitting into a conversation about life, relationships, and dreams while his pen distorts the image. The five-minute timer often becomes negotiable; Reno tends to linger to deepen human connection rather than chase speed. The result is not just a drawing but a shared experience—an invitation to laugh, talk, and reflect on what makes us human.
A Moment That Proves the Power of Imperfection
One of Reno’s most touching moments came during his second week, when a nervous 10-year-old offered $5 from his father. Reno warned the portrait might not be pretty, but when it was revealed, both laughed for two and a half minutes. “That moment was really a clear indication that this is something genuine and positive,” Reno said. This small scene encapsulates the mission: to transform a feared failure into a moment of connection that resonates far beyond a hastily drawn face.
From Market to Movement: The Reach of a 'Terrible Portrait'
Since May, Reno has completed about 600 portraits and built a global following on Instagram at @terrible.portraits. His work has earned features in the Washington Post, Chicago Tribune, and CBC Radio. Questlove reportedly requested a commission, and Wilco invited him to sketch them before a Salt Shed performance. The phenomenon has also created a community: Reddit’s Chicago page celebrates him, regular market-goers plan their Sundays around his appearances, and his work has inspired couples to embrace imperfection in weddings and private events.
A Lesson Beyond Laughter: The Value of Human Connection
Reno argues that art can be found everywhere, but we risk losing the art of face-to-face communication in an era of AI and ChatGPT. “I strongly believe in art being everywhere,” he says, “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.” The joy his portraits bring—whether at weddings, bar mitzvahs, quinceañeras, or bar gatherings—suggests a simple truth: sometimes the most beautiful thing we can create is a moment of genuine human connection, even if the portrait looks nothing like the person.
