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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.”

Instagram (@terrible.portraits)

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.

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A chat with Devon Rodriguez, the artist who surprises subway riders with epic portraits

The artist with over 8 million Instagram followers shares the best reaction he's had from drawing a stranger's face and more.

Getty Images for Meta

Subway portrait artist, Devon Rodriguez, shared what he loves most about drawing people's portraits.

Devon Rodriguez has known he had a talent for drawing since the first grade, when he would spend his lunch period drawing whatever his classmates requested in their notebooks. That's also when he learned he could make something from his art.

"l'd be like, 'All right, you guys have to give me some some of your chicken nuggets, because at this point I need something for this,'" Rodriguez says.

Years later, in 2010, an art teacher gave him an assignment to draw a stranger on the subway to practice portrait drawing. That assignment, along with Rodriguez's entrepreneurial spirit and the wisdom to leverage social media, would lead the artist to internet fame and the career he always dreamed of.

You may have seen viral videos of Rodriguez drawing gorgeous portraits of people on the New York subway and their stunned reactions when he gives them to people. Upworthy caught up with him after the Meta Sonic Listening Party during Miami Art Week, where Rodriguez stretched his creative muscles on the MetaQuest 3, learning to play the piano for the first time. The event was a part of Meta's multi-year "It's Your World" campaign—a call to action for the next generation to pave their path on their own terms—and Rodriguez shared how people can utilize new technologies to expand their skills and creativity.

(This interview has been lightly edited for space and clarity.)

UP: What's the most memorable response you've had from one of your subway portraits?

DR: "There's this one guy I drew and he had like all these face tattoos, and his eyes were tattooed and, you know, people would think he's very scary looking. But when I gave him a drawing, he opened up and was so kind-hearted. It became my most viral video with like 170 million views, and It was because people were like, 'I didn't expect someone that I thought was scary…you, like, humanized him, and you took down the veil of my judgment, and you're teaching me not to judge by a book by his cover.' So things like that I really love because it's meaningful beyond going viral, you know? It's changing thoughts."

UP: What's the best part of drawing someone's portrait?

DR: "I love everything about it. I can't explain it, but even when I'm not drawing, I'm always staring at people. Like, sometimes I forget that I shouldn't stare at people. I'll look at their eyes or their ear and be like, 'Oh, I wonder how I would draw that. That looks cool.

And then also, you know, just knowing—I don't want to sound cocky, but—knowing that I'm good at it. It's kind of like a party trick, getting people's reactions, like, 'Oh my God! It's me and my face and my individual features!' You know, they're so impressed by it, so it's fun."

UP: When they see themselves the way you draw them, are they surprised by their own beauty?

DR: "Yeah, I think so. Don't they say, when you look in the mirror, it's not really a true portrayal of the person? And then when somebody else sees them, that's how they truly look. So maybe there's something like that, where they're like, 'Oh wow, this is the way other people see me.' That different perspective."

UP: Take us back to when you were younger, before you had millions of followers and people knew about you and your art. What did you dream about doing?

DR: "This is exactly what I dreamed. And it's crazy—it's actually beyond what I dreamed. My dream was to become a big artist, a famous artist—it's cringe to admit that, but it's just the truth. But there's no real route or formula to become that. So. I just feel blessed that somehow I used whatever resources that were available to me, which was social media, to make it happen.

I'm always telling this story about how I took things into my own hands with like social media. Like with Instagram—I literally dropped out of college in 2015 for Instagram because I was like, why am I trying so hard for this art degree? I could just become an Instagram artist and then get clients from that instead of wasting my time and not knowing if I could make it. I feel like I have different choices than, let's say, my parents did because social media wasn't around."

UP: How do you think art in general makes the world a better place?

DR: "I think it's just one of the really positive sides of humanity—just creativity and seeing somebody create something with their hands that looks so beautiful, and it's so profound, and you get this strong feeling from it. That's, like, the light side of humanity, you know? It changes the world. When you watch somebody sing a beautiful song and you know they've been practicing for 20 years, it's like, wow. It's moving."

UP: What was the Meta Listening Party experience like for you?

DR: "The listening party was Meta introducing us to their new technologies, like the MetaQuest 3 and the Ray-Ban smart glasses. I own a MetaQuest, so I was already familiar with that. They have this graffiti game where you spray paint, and I was always so impressed by how realistic it is compared to real spray paint. Even when you move, it's like subtle things that only an artist would know. Like when you spray paint and flick the can, how the flair would be exactly [right] and like the distance from the wall—so many little subtle things.

At the Meta party, they were showing us PianoVision, and they had a professional pianist, and he was talking about how close it is to reality. So it was just like a whole campaign showing us all their technology and how accessible it is for people to learn things. Instead of buying a whole piano or buying a whole art kit—let's say you want to paint portraits or something—with the MetaQuest you have access to all of that.

Then I got to perform what I learned on the piano in front of all these people. I was a little nervous, but overall it was all fun."

two men sitting at a piano, one wearing a MetaQuest headset

Devon Rodriguez and Austin Millz played on PianoVision with Meta Quest 3 at the Meta Sonic Listening Party in Miami on December 09, 2023.

Getty Images for Meta

UP: As someone who works with traditional mediums, is it surprising to you how advanced technology has gotten? Or is there still a gap to bridge in terms of working with paper and pencil versus working with something totally digital?

DR: "Yeah, it's actually very close. I feel like people don't really realize it until you actually put it on. Like you have to try on the Quest and experience it for yourself, because it's shocking how advanced it is."

UP: What advice do you have for aspiring artists?

DR: "My advice is to just really find what you're passionate about because then that's gonna pull you—you're not gonna need motivation, you're just gonna want to do it. So like, don't draw people on the subway just because you see me doing it and it works. Don't do this because you see another guy doing it. Do something that you really love and then you'll be the best at that, because no one's gonna have to tell you to do it. You'll have your own drive."

UP: What's coming up in the near future for you?

DR: "Like three months ago, I started this series where I go up to strangers and I sit down on the street with them and talk to them about their life while I'm drawing them. And I did some traveling to Europe last year, so next year I want to pick 12 countries and go explore and film constantly, like exploring and learning about all these people and cultures while I'm drawing all of it. And then creating a whole series, and putting them into like a book of drawings of people from around the world. Yeah, so that's my next plan."

You can follow Devon Rodriguez on Instagram and learn more about the MetaQuest 3 here and the new Ray-Ban Meta smart glasses here.

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Autistic artist draws animal-mashups on request and it's mesmerizing to watch

Drawings by Trent/TikTok

Trent takes requests for animal drawings and creates them with no mistakes.

Some people are born with a knack or natural talent for certain things, from sports to music to math to art. At some point, it becomes hard to differentiate between people who are highly trained and people who are naturally gifted, but occasionally a person's innate abilities are abundantly clear.

Such is the case with Trent, a 24-year-old artist who has gathered a huge following with his on-request animal mash-up drawings. Trent has over a million followers on TikTok. He also has level 3 autism, which impacts his ability to communicate and necessitates help and support with day-to-day functioning. Trent's parents are his caregivers, and they use TikTok to help Trent share his art, champion his work and answer people's questions about autism.

Autistic people sometimes have unique talents, which can manifest as special abilities in memory, math, music, spatial awareness and more. Trent's parents say he started drawing at as soon as he could hold a pencil. He used to draw on everything—walls, furniture, toys, as well as paper—and his favorite thing to draw is animals. His parents nurtured and encouraged this love of drawing, and when you see how effortlessly he draws people's animal mash-up requests, you can see why.

In a recent video, Trent drew a "disco zebra with an afro," a "boxing gorilla" (which he interpreted a bit differently) and a "tiger butterfly." Watch:

@drawingsbytrent

Check out Trent’s art and merch in his store! #autistic #artist #fyp #trenttok

No pencil sketches. No erasing. No re-doing. Trent is able to draw what he sees in his mind's eye, using a permanent marker to make a line drawing of it in seconds. It's mesmerizing to watch.

People have asked if Trent ever makes a mistake and starts over. His dad says no.

"We have never seen him, in 24 years, crumple up a piece of paper and throw it away and start over," he says.

Very seldomly, he'll draw a line and then shift his idea, never going back to incorporate that line. But otherwise, he just draws.

Check out the recent drawings he's been doing of groups of animals with different facial expressions:

@drawingsbytrent

Reply to @melissabolos #autism #artist #fyp #trenttok

Trent doesn't always use a Sharpie—he usually draws in pen. (Why use a pencil if you don't make mistakes?)

@drawingsbytrent

Real time #trentsview #artist #artistsoftiktok #asd #autism #fyp #foryoupage

And his drawings can get really interesting and creative as well. For instance, here it looks like he made the animals wear their noses and snouts as hats:

@drawingsbytrent

#trenttok #autisticartist #fyp

Trent has been impressing people with his cartoon animal drawings for many years. This video of him drawing chalk animals on the family trampoline went viral in 2017:

Trent now has a coloring book, a children's book (written by his parents and illustrated by Trent), and greeting cards for sale. The Drawings by Trent website also sells t-shirts and explains the purpose of the online store:

"At Drawings by Trent we want to encourage families to help their children achieve their full potential, educate communities on the important role individuals of all skill and ability levels play, and inspire everyone to discover and use their own talents. Part of accomplishing those objectives involves helping Trent become a productive member of society while doing something he loves (that's what we all want, right?). When you purchase a piece of Trent's art you are not only supporting him, you're giving families hope."

It's great when anyone gets to do what they love and get recognized for it. Check out the Drawings by Trent TikTok channel for more.


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Self-taught artist makes hyperrealistic portraits with just a basic Bic ballpoint pen

Oscar Ukonu/Instagram, Art Insider/YouTube

Maybe it's because I'm a writer, but I'm a bit of a pen snob. Even if I'm just making a list, I look for a pen that grips well, flows well, doesn't put too much or too little ink into the paper, is responsive-but-not-too-responsive to pressure, and doesn't suddenly stop working mid-stroke.

In other words, the average cheap ballpoint pen is out. (See? Snob.)

However, Oscar Ukono is making me reevaluate my pen snobbery. Because while I'm over here turning up my nose at the basic Bic, he's using them to create things like this:

Um, yeah.

Ukonu is a self-taught artist from Lagos, Nigeria, who creates hyperrealistic portraits using just a Bic ballpoint pen. And not the fancy kind—the super simple clear ones with the pointy lids you buy in a 12-pack because you know you're going to lose half of them around the house anyway.

His drawings look like blue-washed photographs, but they're all hand-drawn with a Bic. (Or more accurately, with around 10 Bics, since the nubs start to wear down as he uses them.) How he makes the most average ballpoint pen strokes do what he does seems like nothing short of magic—even when you watch him do it in real-time.

The techniques he uses are pretty standard—hatching (parallel lines), crosshatching (perpendicular lines), and scribbling (basically what it sounds like). But he uses them on a minutely detailed level, working from multiple photos of the same subject, and the result is portraiture that looks so real it's almost surreal.

Artist Draws Hyperrealistic Portraits Using Bic Ballpoint Pensyoutu.be

Ukonu began his journey with hyperrealism when he was in architecture school and fell in love with ballpoint after feeling unsatisfied with the ink pens he was using. "I spent a lot of time looking at different mediums and drawing tools," he told Vsionvry. "But the first time I tried the ballpoint pen that was in 2014, and it just clicked..."

According to his website, Ukonu "explores black identity and pride in an increasingly globalized world, as well as ideas surrounding Afrorealism" in his art. (Afrorealism is a movement that straddles optimism and pessimism about Africa, with a genuine acknowledgment of the difficulties facing the continent and the placement of Africans in the central role of its development.)

Ukonu calls his work "a practice in time and patience" with an average piece taking him somewhere between 200 to 400 hours to complete. That time and patience pays off as prints of his work—not the originals, just prints—can sell for up to $600.

That braid he's working on in the video? That was this. With a Bic ballpoint. How?


And the newspaper wrapped around the woman's head? He has a whole series of pieces that feature that concept, which he calls "THE DISINFORMATION OF A REPUBLIC."



If you're new to hyperrealistic art, it's similar to—and has its roots in—photorealism, a style in which someone draws exactly what they see in a photo. But instead of drawing a direct copy of a photograph, hyperreal artists use photos only as a reference. That's why the video explained that Ukonu used around 20 photographs (out of hundreds taken) to draw one of his pieces. Rather than an exact replica of a single photograph, the final product is a wholly unique image, even though it looks like it could be a photograph.

It's common for hyperrealists to evoke emotional, social, cultural, and political meanings in their works, which shows clearly in Ukonu's art. And the fact that he can create such beautiful images with a cheap, disposable Bic ballpoint is proof that the talent of the artist is more important than the quality of the tools. (A truth that I will keep in mind when I reach for a pen for any purpose after seeing this.)

You can find more of Ukono's work on Instagram and on his website.

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