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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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Sales for GoodPop are surging after husband's obsession over watermelon flavor goes viral

The story of this full blown love affair over a simple popsicle is a must-watch.

Photo credit: Canva

Sometimes when the taste hits, it really hits.

A big part of marriage—or simply living with another person—means learning to love the little quirks of the person we're coexisting with. Be it their routines, hygienic habits (or lack thereof) or strange obsessions.

For Eli McMann, that meant embracing his husband’s years-long, uncontrollable compulsion for GoodPop watermelon-flavored popsicles.

“He tried them, and was like, ‘this is the best thing I’ve ever had in my entire life,’” McMann recalls in a now-viral TikTok.


After that fateful moment, McMann noticed his husband eating “ridiculous” amounts of these watermelon popsicles (the GoodPop brand, specifically). Their freezer was filled “to the brink,” the house would be riddled with used popsicle sticks… McMann's husband even commandeered the freezers of all of their friends as well, just in case they happened to be there and a craving struck.

Eventually McMann thought to himself “is there a problem? Am I supposed to have an intervention?” He went to X trying to get answers as to how these frozen treats could have taken over their lives, which unfortunately only inspired curiosity in other folks who decided they too must try this tantalizing watermelon popsicle.

Lo and behold, the trend took off so much that GoodPop reached out to McCann, specifically thanking him (well, his husband, rather) for causing their sales to skyrocket across the country, and even offered to send them some free merch.

“It’s been amazing to see so many new people discover GoodPop in such a real, unscripted and joyful way," GoodPop's Founder/CEO Daniel Goetz tells Upworthy. "We’ve been doing this for 15 years - crafting feel-good frozen treats with integrity - and to see all this love come to life has been so incredibly humbling and exciting."

And that just makes this hilarious story even sweeter when you learn more about the fact that GoodPop is a pretty cool company with real people behind it trying to make a positive impact in the world.

"I’m so happy for everyone this impacts - from to our Texas watermelon farmers, to our team that cuts the melons, to our nonprofit partners across the country - we we are all able to share in this viral moment," Goetz added.

And now, McCann’s husband is practically their new brand ambassador, wearing all the branded hats, shirts, gloves, etc, everywhere he goes. They of course also send boxes upon boxes of popsicles for them to sample. If McCann thought GoodPop was taking over his life before…


Little did they know that soon, their popsicle luck would run out. About three minutes into the video, McMann shares that a few days prior, his husband let out a blood curdling scream from the other room. Worried something had happened with their baby, he rushed into the other room only to find the real reason behind the scream: their grocery store would no longer carry his husband’s drug of choice. In fact, no surrounding stores would carry them either. Naturally, this sent McMann’s husband into a “full blown spiral.”

“This man spent the better part of two hours calling grocery stores within a fifty mile radius," McMann said. Eventually he found one a mere twenty miles away, and began planning how he could make regular excursions out to buy the popsicles in bulk.

“I am not a religious man, but I am begging you people to pray for us,” McCann concludes.


GoodPop, of course, seized the opportunity to deepen its bond with its number one fan. In a subsequent series of videos, we see a GoodPop delivery driver supposedly pedaling some boxes all the way from GoodPop headquarters in Austin,TX to Salt Lake City, where McMann and his husband live. The company even changed their TikTok bio to read “Eli’s husband’s favorite pop.” In an exceedingly ironic twist of fate, a photo of McMann begrudgingly holding a watermelon popsicle is now GoodPop’s profile pic, making him more of a mascot for the brand than his husband.

@goodpop

We’re on our way! Stay tuned and follow our journey to get pops to Eli’s husband! 🍉💨 . #popsicleemergency #goodpop #watermelonpopsicle #goodpoppopsicle #goodpopwatermelon #watermelonpop

In a time when companies seem more and more out of touch with the people they supposedly serve, and when the internet seems to continuously disconnect us, moments like this feel all the more special. McCann certainly didn’t share this little story about his husband’s popsicle obsession in order to go viral, but viral went nonetheless, making so many emotionally invested in a product they might have otherwise never known of. In turn, GoodPop could have simply used the viral video to promote their products, but instead established an actual human relationship. Just a little dose of TikTok using its powers for good.

By the way, even if watermelon flavor isn’t your thing, GoodPop has other delicious flavors, along with a ton of other tasty, good-for-you treats, like ice cream sandwiches, orange creamsicles, Mickey Mouse pops, and more. Check out their website here.

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Gen Z and Millennials have revealing chat about how differently they've experienced the 2000s

"Millennials had dial up internet. And a life before that internet was created."

Images via Canva

Gen Z discusses the biggest cultural differences between them and Millennials.

Gen Z (those born between 1997 and 2012) and Millennials (those born between 1981 and 1996) only have a handful of years between them. But if you ask them, they were raised worlds apart.

In an online forum discussing generational differences, a member named @No_Title_615 posed the question: "Why are Gen Z so much different to Millennials?" They went on to share, "So I grew up during the 2000’s and 2010’s and as a society I felt like we were honestly in a really good place culturally. However as we entered the 2020’s I felt a big shift in society."

The shift? A noticed change in overall optimism to pessimism. "Suddenly there was so much more doomerism. The optimism of the 2010’s pretty much went away," they wrote.

The post prompted many Gen Zers and Millennials to add their thoughts and opinions about their differences growing up--and they did not hold back. From societal norms to technology and more, here are the most interesting responses from Gen Z and Millennials.

"Millennials grew up and learned the internet and technology as it was happening whereas GenZ will utter phrases like “wtf do you mean, no internet?” at some point in their lives." —@Quiet-Donut2192

"I feel like the optimism of the 2010s was more an Obama 2nd term thing than an all of the 2010s thing." —@Someperson727

"Millennials had dial up internet. And a life before that internet was created." —@grom513

dial up, dial up internet, internet, aol, internet memeDial Up The Struggle GIFGiphy

"The way that I see it, is that the 2010’s were right after the housing crash, and ppl became more optimistic, going to clubs more and such. However, post-COVID, I feel after that crisis, music I particular seems to be getting better. After a social crisis, the music seems to reflect the feelings that everyone is feeling. Then afterwards, a couple of years or so, the music becomes more uplifting and even reflective. This is the period that we’re in, imo. Hope this makes sense." —@Maxi-Lux

"9/11 and COVID were large reasons that separate Gen Z and Millennials. Millennials had an understanding of what life was like before 9/11, not Gen Z. Millennials had a taste of the workforce before COVID, not Gen Z. Gen Z grew up and faced adulthood in the midst of crisises, Millennials had the taste of the normal life before it got taken away." —@XConejoMaloX

scrolling, smart phone, iphone, scrolling mindlessly, scrolling gifAdd Hasan Minhaj GIF by MOODMANGiphy

"Smartphones changed everything. My upbringing was largely the same as millenials, but when smartphones started getting popular, everyone I knew got busy, cold, and distant. I'd try having conversations with people and they'd just stare at their phones the whole time. I think constant internet access has left people fragmented, with our heads in the clouds. You could live right next to each other but have nothing in common, because everything is online now." —@OnTheRadio3

"I say this all the time and frequently get a lot of flack for it but the doomerism is a byproduct of inexperience. People who spend most of their time online or in videogames or otherwise rotting away alone at home aren’t gaining much in the way of life experience but they don’t want to come off to others (or themselves) as naive, sheltered, etc. so they adopt this kind of idiotic cynicism to stand in for the wisdom of experience. Others see this and basically copy it because if you don’t know better then it sounds very worldly and jaded. Gen Z exhibits this due to the isolation and terminally online nature of their upbringing." —@Woodit

party rock, millennials, party rock dance, dancing, shufflingdance party everyday im shufflin GIFGiphy

"Gen Z refused to Party Rock." —@One_Huckleberry_

"Millennials had access to the world’s information without it being algorithmically weaponized against them during their formative years." —@Messiah_Thomas

"We know what it’s like to not have the internet or phones on us 24/7. Also we know what it’s like to play outside and be bored to our core." —User Unknown

play outside, outside, outdoors, playing, boredPlay Go GIFGiphy

"I mean bruh, 2020 literally started off with a pandemic, it’s not the best reference point to go off of plus we are only halfway through our current decade. I think nostalgia for happier/youthful times is playing a part in warping your perspective. There’s a lot of factors though, Gen Z as a whole has been disenfranchised by a feeling of lack of purpose and bad financial prospects. It’s not something I’d arbitrarily chalk down to our generation as a whole, but rather the material conditions of our modern day environment and things happening beyond our control. For most of us, we were hit by the Covid lockdowns right after or during high school so key years of our youth got utterly fucked and what came after was bitter sweet. Things got a hell of a lot more expensive in the last few years and wages aren’t sufficiently rising to keep up with inflation. so that plays a huge part. More youth are realizing the contradictions and flaws within our economic system and yearn for change. Tough times can create a lot of animosity and frustration in people." —@Triscuitsandbiscuits

"I wonder if the fact that there was a global pandemic had anything to do with decreasing levels of optimism." —@AdMurky3039

tiktok, tiktok dance, tik tok choreo, tiktok dancing, dance tiktokJimmy Fallon Dancing GIF by The Tonight Show Starring Jimmy FallonGiphy

"Internet, YouTube, Tik Tok. Constantly exposed to what we would have considered bad influences before." —@Electrical-Lead-3792

"We had an incredible upbringing. Music was great, the state of the world was great (besides 9/11). Pop culture was great. Everything was just getting better and better. Movies, games, phones, internet, cars getting cooler and cooler, buildings getting cooler and cooler. People getting cooler. And we learned almost everything through experiences, socializing, mentorships, taking advice, listening to our elders, asking questions, experimenting, arguing, challenging ourselves, breaking ourselves down, lifting ourselves up, and figuring what this world means to us. While the new generation, the minute they’re unsure about something they run to ChatGPT. They don’t take risks. They don’t argue anything, the right opinion is the most popular or upvoted. They’re not insightful. They don’t value perspective. And everything is as good as it gets for them. Different times. We were like the roaring twenties before 1929 happened." —@SasukesFriend321


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