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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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They said there's no English rhyme for "silver." Eminem just obliterated the challenge.

Don't ever let them tell you anything is impossible.

By Scott Kinmartin - CC BY 2.0

Someone challenged Eminem to rhyme "silver," and he crushed the challenge without breaking a sweat.

It started with an innocuous Tweet from a popular account called UberFacts.

"There's no word in English that rhymes with 'silver'" the post read. For long-time English speakers, this isn't exactly news. We've been hearing about random words that seemingly have no rhymes for as long as we've been talking.

A user then decided to call in an expert to confirm whether this was actually true. So, they tagged rapper Marshall Mathers, better known as Eminem, in a post issuing a challenge: "You have 24 hours!" the user joked. If anyone could disprove the so-called fact, it would be him, the wordplay master himself who once rhymed "calm and ready" with "Mom's spaghetti."

eminem, marshall mathers, rap, hip hop, rhymes, english language, rhyming words, rhyme challenge, silver, purple, orange Slim Shady to the rescue. Giphy

Eminem himself responded a day later and completely obliterated the challenge:

"Silver

pilfer

kill fer

Gilbert's

still hurts

steel shirts

Bill Burr

milf word

off kilter

no filter

chill brrrr

feel burn

still slur

will stir

Trent dilfer

Val kilmer

Still third

shield her

he'll squirt

Steven Spielberg

Lil twerp

Wilshire

She'll purr

Kill birds

milk curd

feel worth

Real nerd

Stans documentary I liked your film sir," he wrote in his own post.

If you're familiar with his music, you can almost hear the post in his voice. You can imagine him ripping this off as a verse in one of his songs. You also immediately get the sense that he could have easily kept going, but chose to stop the list there. Point proved.

Oh, sure, you can come up with a list of more words with no rhymes: Purple, month, ninth, opus. Pretty sure Eminem will have no problem tearing the list to shreds.

Eminem's post went viral and was reposted nearly ten thousand times. Thousands of people commented to share their admiration for the hip-hop legend:

"And that's why he's the GOAT" one user wrote.

"He took silver and did a verse of Gold!" another added.

"Eminem can make any word rhyme with any other word," said another.

(Oh, and "pilfer" was right there in front of us this whole time, if you can believe it! Merriam-Webster even chimed in to suggest the little-known "chilver.")

Eminem is known as probably one of the best rappers of all time specifically when it comes to wordplay, rhymes, and clever lyricism.

In a 60 Minutes interview with Anderson Cooper from 2011, Eminem shared a little bit of his approach. Cooper offered up the notion that nothing in English rhymes with "orange," and Eminem was actually almost offended.

"If you're taking the word at face value... nothing is going to rhyme with it exactly," he said, noting that the art is in twisting and contorting words and phrases. Thinking outside the box. Then, off the top of his head, he ripped off a short rhyme:

"I put my orange four-inch door hinge in storage and ate porridge with George."

Cooper asks him if he walks around all day thinking about rhyming words. "Yeah. All day. I actually drive myself insane with it," Eminem said.

A young Marshall Mathers would read the dictionary even though he wasn't a "good student" academically. "I just thought, I want to have all these words at my disposal, in my vocabulary, at all times, whenever I need to pull them out."

- YouTube www.youtube.com

Why are we so fascinated with a good rhyme?

You have to admit that reading or listening to Eminem's creative rhymes for "orange" and "silver" is oddly satisfying.

That's because rhymes, or even just rhythmic poetry, does something different to our brain than other forms of speech or prose.

"The brain's reaction to poetry indicates a deep, intuitive connection to verse, suggesting that appreciation of poetry is within our neurological structure," according to How Stuff Works.

We also perceive things that rhyme as 22% more true than statements that don't, which is why so many slogans and catchphrases utilize rhyming words. That also plays a big role in why music and song are so emotionally powerful, even when the lyrics are relatively simple.

Finally, it's really pleasing to our brains when we're able to predict words and identify patterns. That's a lot easier and more fun to do in rhyming forms like rap, song, and poetry versus prose and regular speech.

It's awesome to see an artist and master at work in Eminem's post and interview. It should inspire you to think outside the box and remember that, whenever someone tells you that something is impossible, the real art is in proving them wrong.

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Fatherhood

Magician creates the most fantastical 'glow room' for his daughters and you can too

"Their shadows stay on the wall!"

Photo credit: Canva

A magician performs a trick. A person is painted in glow-paint.

It's become pretty cheesy to utter things like, "There's magic everywhere," (especially if you creepily whisper it.) However, if you happen to be lucky enough to visit magician Justin Flom's home, it's literally true. Every single square foot of his home seems to be magical, which is pretty fortunate for his young kids. Truly, their dad's imagination knows no bounds.

A few months back, Upworthy's Heather Wake covered the "wildest house tour" ever, wherein we see Flom's fever dream of a home in a video presented by his wife. Wake describes "the toilet paper wall in the bathroom (cause why not?), a 'cozy' loft made of netting above the stairs for the kids, and a 'Dr. Pepper passageway' that leads to a hidden door in the wallpaper that opens to their Blockbuster-fied movie room."

The house has become a recent viral sensation again, as Flom's sister has now made her own personal video from her point of view. She seems especially dazzled by the disco room, the hidden door INSIDE the foam pit, and yes, the glow-in-the-dark room.


In pushing the boundaries of whimsy, Flom recently shared a new clip on TikTok where we see him pouring what looks like oxidized phosphorous into a painting tray. When applied to the wall, the green, glowing paint makes it look as if he's created his very own Aurora Borealis within the walls of his home. In a voiceover, Flom shares, "This room glows in the dark and you can leave your shadow on the wall."

We then see Flom's daughters helping create the, ahem, magic. He continues, "The glow-on-paint goes on clear and I give my daughters special flashlights so they can draw on the wall…with light."

@justinflom

Their shadows stay on the wall! 💡🔦

As if that wasn't cool enough, he says, "It's done, and I'm showing you right now, the glow room, hidden behind our tunnel of doors." We then see five different doors being opened, including a red door, what looks like a Cookie Monster door, a brick wall door, and a final door that resembles the spiral of a safe. Once inside, he says to the girls, "Doesn't look like anything, right? The wall looks normal, doesn't it? But wait. Ready?"

They nod. "On the count of three, we're gonna turn out the lights and this room is gonna glow. You ready for it? Three. Two. One…!" Flom turns out the lights, and, as promised, the walls glow in a bright Oz-like green. What happens next is like scenes from a Pixar film or perhaps Wicked: When they press their bodies against the green wall, they make a shadow that remains as though it has been painted on by the finest artist. Then, on top of their OWN shadows, they can create whatever they'd like using plain old lights as their brushes.

Once one gets over the absolute awe of it all, it's hard not to wonder…how was this possible? We turn to the comment section, which first showers Flom with compliments. One person writes, "I want to do this with my adult money." Another, "The childhood I wished I'd had."

green phosphorous, green glow, glowing, lights A gif of the Northern Lights Giphy, Yatri design

Just a tiny scroll down, and a TikToker seems to have found the paint. "Is it the Risk Reactor glow paint?" Though they note it's expensive ($400), many agree it's worth it. Someone asks, "How do they get the shadow off the wall?" Another responds, "You cover the area, shine a light, and the bit that's covered doesn't glow."

Luckily, there is a cute, wacky video on YouTube that gives us an actual step-by-step on making your own glow wall, should you want one. YouTuber UV Black Lights uses what he calls a "blinds thing" type surface and illustrates that first you want to "clean the surface" really well. Then, using "glow in the dark phosphorescent paint," he shares, "All you have to do is just paint."

- YouTube www.youtube.com

For this tutorial, he demonstrates that he's using the Wildfire paint brand and recommends two or three coats over a primer (if one has the patience). We then get a chyron AND a voiceover exclaiming "three hours later," followed by a shot of the surface hung up, "all dried and ready to go."

Once the sun goes down (since he's presenting this experiment in his garage), he explains, "So what we're using here is just a little laser. It doesn't need to be black light. All you have to do is have some kind of light source." (Remember, Flom used tiny flashlights.)

He then shows off shadow art, similar to Flom's earlier video. Beautiful, majestic, and best of all? Doable!

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'Wicked' author reveals subtle clue in 'The Wizard of Oz' that Glinda and Elphaba were friends

"I fell down onto the ground laughing at the thought that they had gone to college together."

Public domain
Gregory Maguire was inspired by a line in the original 1939 film "The Wizard of Oz."

Have you ever watched a movie or read a book or listened to a piece of music and wondered, "How did they come up with that idea?" The creative process is so enigmatic even artists themselves don't always know where their ideas come from, so It's a treat when we get to hear the genesis of a brilliant idea straight from the horse's mouth. It's often not what you would expect!

If you've watched Wicked and wondered where the idea for the friendship between Elphaba (the Wicked Witch) and Glinda (the Good Witch) came from, the author of the book has shared the precise moment it came to him.

The hit movie Wicked is based on the 20-year-old hit stage musical, which is based on the novel Wicked: The Life and Times of the Wicked Witch of the West written by Gregory Maguire. It says a lot about how powerful the story is that it has succeeded in so many different mediums and continued to find new audiences that connect with it.

While the musical is a simplified version of the 1995 book, the basic storyline—the origins of the two witches from "The Wizard of Oz"—lies at the heart of both. In an interview with BBC, Maguire explained how Elphaba and Glinda's friendship popped into his head.

wizard of oz, wicked, wicked for good, wicked movie, wicked musical, wicked novel, gregory maguire, art, artists, writers, authors Ariana Grande as Glinda in the "Wicked" film Giphy

Maguire was visiting Beatrix Potter's farm in Cumbria, England (Potter was an author and illustrator who created Peter Rabbit) and thinking about "The Wizard of Oz," which he had loved as a child and thought could be an interesting basis for a story about evil.

"I thought 'alright, what do we know about 'The Wizard of Oz' from our memories,'" he said. "We have the house falling on the witch. What do we know about that witch? All we know about that witch is that she has feet. So I began to think about Glinda and the Wicked Witch of the West…

"There is one scene in the 1939 film where Billie Burke [Glinda] comes down looking all pink and fluffy, and Margaret Hamilton [The Wicked Witch] is all crawed and crabbed and she says something like, 'I might have known you'd be behind this, Glinda!' This was my memory, and I thought, now why is she using Glinda's first name? They have known each other. Maybe they've known each other for a long time. Maybe they went to college together. And I fell down onto the ground in the Lake District laughing at the thought that they had gone to college together."

Maguire must have thought the idea of Glinda and The Wicked Witch attending college together was absurd at the time. What a kooky idea! But he pursued it nonetheless and, well, the rest is history.

wizard of oz, wicked, wicked for good, wicked movie, wicked musical, wicked novel, gregory maguire, art, artists, writers, authors A photo of author Gregory Maguire.By Jeremy Goldstein/Flickr CC BY 2.0

In "Wicked," Glinda and the Wicked Witch, Elphaba, meet as students at Shiz University, a school of wizardry. They get placed as roommates, loathe each other at first, but eventually become best friends. The story grows a lot more complicated from there (and the novel goes darker than the stage play), but it's the character development of the two witches and their relationship with one another that force us to examine our ideas about good and evil.

Watch his explanation and inspiration here:

Maguire also shared with the Denver Center for Performing Arts what had inspired him to use the "Wizard of Oz" characters in the first place.

"I was living in London in the early 1990’s during the start of the Gulf War. I was interested to see how my own blood temperature chilled at reading a headline in the usually cautious British newspaper, the Times of London: 'Sadaam Hussein: The New Hitler?' I caught myself ready to have a fully formed political opinion about the Gulf War and the necessity of action against Sadaam Hussein on the basis of how that headline made me feel. The use of the word Hitler – what a word! What it evokes! When a few months later several young schoolboys kidnapped and killed a toddler, the British press paid much attention to the nature of the crime.

"I became interested in the nature of evil, and whether one really could be born bad," he said.

"I considered briefly writing a novel about Hitler but discarded the notion due to my general discomfort with the reality of those times. But when I realized that nobody had ever written about the second most evil character in our collective American subconscious, the Wicked Witch of the West, I thought I had experienced a small moment of inspiration. Everybody in America knows who the Wicked Witch of the West is, but nobody really knows anything about her. There is more to her than meets the eye."

Authors and artists—and their ideas—help hold a mirror up to humanity for us to see and reflect on who we are, and "Wicked" is one of those stories that makes us take a hard look at what we're seeing in that mirror. Thanks, Gregory Maguire, for launching us on a collective journey that not only entertains but has the potential to change how we see one another.

The second Wicked film, For Good, hits theaters in November 2025.

- YouTube www.youtube.com

This story originally appeared last year. It has been updated.

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