If you’ve got a face, Adam Dressner wants to paint it.
Dressner, a former corporate lawyer, has made a name for himself as a self-taught painter known for wheeling his “art cart” of painting supplies to Washington Square or Central Park and making loose, expressive plein-air portraits of the eccentric New Yorkers he meets.
This past week, Dressner took his cart to 1969 Gallery in Tribeca, where he sat beneath a brown butcher paper sign reading “Fine Art Portraits” in Tom Sachs studio-style scribble, completing 18 paintings in the days leading up to “Hello Stranger 2,” his debut solo gallery exhibition, which opened Friday night.
Composed of more than a dozen large-scale oil paintings and a salon wall of 60 12 x 9-inch acrylic portraits, the exhibition is an evolution of “Hello Stranger,” a show he co-presented with jeweler Greg Yuna last September, in which Dressner live-painted subjects at Grand Central Terminal over the course of three days.
Some of the salon wall subjects are recognizable—the restaurateur Keith McNally, the infamous grifter Anna Delvey, the rapper Lil Yachty—while others come from Dressner’s milieu, like Rafael, a waiter in his neighborhood, or Mr. Love, a man in his 90s whom Dressner met in the park and has since befriended.
“This is artwork for everybody,” says Dressner. “Everybody’s got a face. When you look at the salon wall of 60 12-inch-by-9-inch boards, you can’t tell the difference between a literary giant like Joyce Carol Oates, or somebody who is an everyday person from the park.”
Many of the subjects attended Friday’s opening, including Oates, Delvey, the influencer Nicolas Heller (known as New York Nico), Leah McSweeney of The Real Housewives of New York, and art collector Carla Shen, along with many of the subjects of his large-scale portraits: the poet Matt Starr, Metro North employee Sunny Suero, and a man named Monty who is known for sunbathing in Washington Square Park. At one point, one of Dressner’s most-painted subjects, David Rosa, entered in a tuxedo, wheeling in a speaker blaring Donna Summer’s “Hot Stuff” and breaking out in a dance, a routine he reprised from the first “Hello Stranger” opening. Dressner, wearing the signature blue baseball cap he is never seen without, watched him, beaming. Other guests included the writer James Frey, actress Sophia Anne Caruso, and artists Jon Burgerman, Lizzy Lunday, and Kristian Kragelund.
In the portraiture tradition of David Hockney, Barkley Hendricks and Alice Neel (who also painted New Yorkers), Dressner pairs vibrant hues and expressive color palettes with flat, abstracted backgrounds, often including details like scarves or hats—or in the case of Starr’s portrait, a stuffed bear—that present an off-kilter, attention-demanding alchemy of the unfamiliar and the everyday. Rob, a particular standout, has a Lucien Freud-inspired grotesque realism that’s upended by the abstract background and stark white splotches of unfinished shoes. “I look at his portraits and I want to know more about the people. They’re very compelling,” James Frey said at the opening. “It’s easy to walk past a portrait without looking at it, and that’s hard to do here.”
The practice’s heart, of which there’s plenty, is interested in subverting the traditional practice of portraiture, which has largely focused on royals, commissions, or anonymous models, in favor of exalting the ordinary, emphasizing organic human connections. Dressner draws inspiration from the Dutch painter Frans Hals, who traversed the social strata with a similar joviality. “I’m interested in flipping the script a little bit,” Dressner says. “I’m interested in documenting people’s reactions to the painting and in celebrating the people themselves.”
Highlighting everyday New Yorkers is a fitting goal for Dressner, who lives and works in the Stuyvesant Town apartment where he has lived since he was 12. An unpretentious approach also makes sense for an artist who is himself newer to the art world. Dressner was working in his first law firm in 2009 when he attended a Francis Bacon retrospective at the Metropolitan Museum of Art. He was so moved by the work that he rushed to Barnes and Noble in Union Square, bought Oil Painting for Dummies, and began painting Bacon-inspired nude triptych self-portraits. He worked on his craft for years while working full-time as a lawyer, until he quit his job to become a full-time artist in 2018.
Dressner’s instinctual approach means that, despite his tight, 30-minute process, his portraits are anything but formulaic. Local New Yorkers are painted in a loose, gestural style with non-local colors—the highlights and shadows rendered as alien as the people who sit for him—creating a sea of faces both strange and moving. “They’re playful and original. He uses color very instinctively,” Joyce Carol Oates said over the phone ahead of the opening. “Sitting for him was delightful. The time passed very quickly.”
Sunny Suero was working for Metro North in Grand Central Terminal when Dressner asked to take a photo reference of them. After about a year had passed, they’d forgotten about the encounter until one of their coworkers asked if they’d seen their portrait in the station. Suero couldn’t believe it.
“I’ve lived in New York City my whole life and it would’ve never even crossed my mind that I’d be in a Tribeca gallery one day,” says Suero, gazing at their portrait. “It’s affirmation I didn’t know I needed until I saw it here and at Grand Central. It’s like, wow, okay. I need to stop viewing myself as ordinary.”
“Adam Dressner: Hello Stranger 2” is on view through October 25, 2025.