“So ugly” it’s… indescribable!

Who says a portrait has to be picture-perfect? At Logan Square Farmers Market in Chicago, every weekend, people are lining up for an experience unlike anything else: “Ugly Portraits & Four Terrible Minutes” for just $5!

And no—you’re not being tricked. You willingly wait your turn just to be artistically disfigured… with the biggest grin on your face!

 Reno – The “Ugly Artist” Who’s Making Chicago Giggle

Sitting in front of you is a young man in a deep blue jacket, soft jazz playing in the background, behind a folding table. Next to him is a gloriously ridiculous sign that reads:

“Ugly Portraits, Four Terrible Minutes, $5.”

Meet Jacob Ryan Reno, 26 – a former communications professional who quit his job in 2024 after realizing corporate life didn’t align with his values. He grabbed a piece of cardboard, splashed it with green paint, set up a tiny booth, and “invented” one of the strangest yet most joyful experiences in Chicago—back in May.

 500 People, 500 Giggles

Since then, over 500 people have sat for Reno’s “ugly” portraits. The drawings may be wobbly, exaggerated, and downright ridiculous—but they have an irresistible charm.

Most aren’t here for art—they’re here for something far more precious: five minutes of pure silliness, a rare pause from the overly serious, overly digital everyday grind.

“When I first started, I thought maybe I’d get four customers and that would be enough,” Reno says, still looking surprised at the demand. “But people genuinely love it—they keep coming.”

 Behind the “Ugly”: Slowing Down in a Too-Fast World

Reno doesn’t see this as “work” in the traditional sense. For him, it’s a gift—a quirky, laughter-filled space where strangers connect. Some people chuckle quietly when they see their portrait. Others burst out laughing so hard they nearly cry.

Victoria Lonergan, a customer and Reno’s former coworker:
“When I flipped the portrait around, I laughed so hard I couldn’t breathe.”
Christian Borkey, another friend:
“Not just me, but my whole group was cracking up. The joy was contagious.”

Reno says nobody has been upset so far. “If you agree to do this, you already have a sense of humor. You know exactly what you’re signing up for.”

 A Little Humor Goes a Long Way

Who needs perfection, anyway? Sometimes, beauty is found in the imperfections—in the goofy, the lopsided, the “what even is that?” kind of art. Over 500 people have proven it: they’re not after a flawless portrait, they’re after a moment of unfiltered joy.

It’s like a tiny reminder to not take life too seriously. Sometimes, you need to let something “ugly” break the ice, lower the walls, and spark real human connection. Happiness, as it turns out, can cost just $5, require only a folding chair, and be delivered by an artist armed with a sketchpad and a mischievous smile.

 From Farmers Market to Parties: Ugly Goes Viral

What started as a small booth in a farmers market has begun to spread. Local media caught wind of the story, and before Reno knew it, he was getting invitations to draw at weddings, housewarming parties, birthdays—you name it.

His “ugly art” has turned into the ultimate party trick—half entertainment, half souvenir, all pure laughter.

Imagine it: you’re at a wedding, the champagne’s flowing, and in the corner, Reno is doodling “hideous” portraits of the guests—each reveal causing a fresh explosion of giggles across the room. It’s chaotic, it’s ridiculous… and it’s unforgettable.

 Why This Works: A Dose of Realness in a Filtered World

We live in an era of perfect selfies, curated feeds, and impossible beauty standards. Reno’s booth is the antidote—no filters, no retouching, no flattering angles. Just raw, honest, and hilariously exaggerated lines.

And that’s exactly why people love it. It’s refreshingly real. You’re not performing for likes—you’re laughing at yourself with a stranger in a farmers market. That’s a kind of authenticity you can’t buy from an Instagram ad.

 What People Take Away

The portraits themselves? They might live on your fridge, in your office, or be proudly framed on your wall as a conversation starter. But what you really take home is the story:

“One Sunday in Chicago, I paid a guy five bucks to make me look like an alien, and it was the best thing I did all week.”

For many, that’s worth far more than a polished photo. It’s a shared memory—one that’s just the right kind of ridiculous.

 So… Would You Do It?

If you were walking through Logan Square Farmers Market, would you stop? Could you sit down, stare straight at a stranger, and let them immortalize you in the most unflattering way possible?

Because if you can, you might just walk away lighter, happier, and a little more in love with the absurdity of life.

Final Word: Ugly Has Never Been So Beautiful

Jacob Ryan Reno isn’t just drawing faces—he’s sketching joy. In a world moving too fast, he’s creating a pocket of time where phones are down, smiles are up, and strangers leave as friends.

Think about it: a man, a sketchpad, a goofy sign, and a crowd willing to pay to look terrible… and yet, it works. Because sometimes, the happiest moments happen when you let yourself be just a little bit ugly.