The Best Really Bad Portraits in NYC: ‘It’s About the Laughter’

Text and Photos By Daniel Krieger

Ricky Brown’s portraits are not just bad. They are, he promises, “really bad.” In fact, he calls them “the worst in New York City.” Yet, every Sunday he sells dozens and dozens of them at the Grand Bazaar on 77th and Columbus Avenue. You may think there wouldn’t be much demand for such art, but he has proven there is.

On a recent sunny Sunday afternoon under a bright blue sky, a crowd of onlookers and customers gather at Brown’s table. He is an artist in residence of sorts at the bustling market, which offers him a steady flow of new customers and admirers from all over.

An eye-catching sign mounted on an old door advertising Really Bad Portraits along with his earnest performative sketching routine attracts much attention, eliciting smiles, laughter and chitchat. After completing a portrait, which takes about 30 seconds per person (at a charge of $5 per subject), there’s the reveal. And customers almost always laugh.

“That is frigging awesome!” exclaims a woman drawn with her daughter. Next comes a father and son, and then a teenage brother and sister. Then a trio of friends, followed by a family of four, and then a group of five friends. They all laugh heartily. Next a solo portrait of a shih tzu-poodle. The comments are consistently favorable: “Amazing!” “Oh my God!” “Wow!” “Great!”

“I love this guy,” a woman says as she walks by, chuckling.

“It’s usually a snowball effect,” Brown says during a lull, explaining that once he starts drawing, people stop to watch, which attracts more people, and inevitably, more portraits and more laughs.

“It’s about the laughter,” he explains. “It’s really just a joke to make people laugh.”

And, it turns out, the performance of this single sustained joke earns him enough money to make a living. Brown, who is 25, lives in Bed-Stuy, Brooklyn, and grew up in Westchester and Colorado. A good day brings in as much as $1,000 from portraits plus tips. He also goes to Washington Square Park a few times a month and occasionally gets hired for events.

He approaches a couple lingering at his sign and says: “Guys, they’re terrible, I promise. Would you like one?” They take him up on it and another rush follows — more couples, more parents with kids, more friends, more bursts of laughter. Two young women waiting on line are smiling as they observe the scene of inspired silliness. Asked why they decided to take part, one says: “It’s cute and quirky, and it’s a little memento of the day.”

“I saw you on Instagram!” says a middle-aged woman who, upon seeing the result, laughs and says: “That’s beautiful! It’s hysterical!” She tells WSR: “There’s really something funny about him saying he’s really bad.”

Next is a five-month-old baby whose mom holds him up for a solo portrait. “Perfect,” says the dad at the reveal. “I love what you’re doing,” says a young woman after getting sketched with her mom. Though not everyone gets (or appreciates) the joke, many clearly do, even the smiling passersby who don’t stop for a portrait. Those who do find the experience uplifting. They play along with the joke, like a dad with his daughter.

“That’s a really bad portrait,” he says upon seeing it.

“As promised,” Brown says, dryly.

Ricky Brown is tall, slender, soft-spoken and low-key, with a pitch-perfect nonchalant, deadpan manner. Wearing a mustard yellow polo shirt, tan shorts and charcoal Allbirds, he swiftly glides a black fine point Sharpie across a sheet of white paper on a clipboard as he scrutinizes his subjects, employing colored Sharpies for dyed hair or redheads. He likes to zero in on accessories, such as earrings or glasses or a hat, whatever captures “the details of their style,” he says.

“Hell yeah,” an animated middle-aged man in a purple paisley shirt blurts out when he sees the sign. He then requests a genre of drawing he never even knew he desired until that moment. “I don’t want a good portrait! How boring is that?” he says.

Thirty seconds later, he calls the result “great.”

“I did my worst,” Brown replies, getting a laugh. Asked why he likes the crude depiction, the man responds: “How could you not love really bad portraits? It speaks to something deep inside me.”

As for the origin of his booming business, Brown says he was stuck at home during Covid and sought a new creative outlet while his pursuit of standup comedy was on hold. So he started drawing, which he hadn’t done since childhood. But he wasn’t very good at it.

“I was trying relentlessly to draw a really realistic, good portrait and was failing,” he says. “Then to free my hand I just drew a really bad one. And right then at that moment I thought, ‘Oh, it would be funny if I offered really bad portraits for money.’”

He worked in a few places around town before landing at Grand Bazaar in November, 2021. “It’s the perfect spot,” he says, given the vibrant, art-focused scene.

The joke rests on the subversion of expectations, i.e. a guarantee of poor quality is not quite how vendors market their services. And in this era of aggressive self-promotion on social media, it’s a refreshingly novel twist. Brown knew it was a cool idea, but he never imagined he could support himself from just this one joke, which he doesn’t upstage with antics that fall outside the gag’s parameters.

“I think it’s all in the advertisement,” he says. “Really Bad Portraits — it’s just a funny novelty item.”

A young, chatty Parisian guy with pink sunglasses who has just come from MOMA is so enchanted with his portrait that he requests two more of friends, from photos.

“I love the concept,” he tells WSR. “It’s funny and cheap. I can get realistic portraits anywhere, but I’ve never seen this before.” Assessing the final product, he is the only customer of the day to declare: “And it’s not really that bad.”