The Lawyer Who Wants to Paint You

When Adam Dressner was twelve, he moved with his father to a two-bedroom apartment on the seventh floor of a building in the Peter Cooper Village housing development, in Manhattan. His dad has moved out, but Dressner, now forty-four, has left only three times: to go college, graduate school, and law school. In the summer of 2009, before starting as an associate at Sullivan & Cromwell, he went to the Francis Bacon retrospective at the Metropolitan Museum and emerged a changed man. He loved making art as a kid, but gave up on painting after a failed foray into oils. Now, with the assistance of "Oil Painting for Dummies," he threw himself into the medium again, only to discover that an eighty-hour workweek left little time for the easel. Shortly before the pandemic, he quit corporate law to commit himself to painting.

On a late-summer Friday, Dressner was in his home studio, with Clover, his gregarious twelve-year-old mutt. A decommissioned library card catalogue held brushes and paint tubes. "That's probably the only piece of furniture in here," he said. He is slim, with dark hair and startling blue eyes that match the cerulean ball cap he refuses to be seen without (he has three). He was in the final stages of prepping his first solo show, "Hello Stranger," which was scheduled to open soon in Grand Central Terminal's Vanderbilt Hall. Canvases were propped and stacked everywhere. Many of Dressner's paintings are big—some are six feet tall—and representational, in a frank, colorful style that calls to mind Alice Neel or a trippy Frans Hals.

"I started with naked self-portraits," Dressner said, pointing to a painting of himself, younger, sans ball cap and everything else, clutching his head in artistic agony. He soon moved on to making paintings of clothed loved ones, including his grandmother, who lived on the eleventh floor.

Lately, Dressner has found his subjects by setting up his easel around the city en plein air. "It turns out I'm a social person," he said. The title of his show—which is co-sponsored by the jeweller Greg Yuna, who appeared in the Safdie brothers' movie "Uncut Gems"—reflects a democratic optimism rarely evident in the art world. "The work is a little bit skewed to the eccentric among us," he explained.

Starting in the living room, Dressner introduced some of the show's subjects. "This is Mr. Love," he said, indicating a painting of a besuited Black man outfitted with a pocket square and bow tie. They met one day in Washington Square Park, where Dressner took reference photos. "I didn't run into him until a full year later," he said. He then went to visit Mr. Love at the senior residence in the Bronx where he lives, and a friendship developed.

Dressner moved on to the hallway, where a sturdily built bather posed impishly against an orange, turquoise, and pink background. "This is David Rosa," he said. "He asked to be painted in a tiger-print Speedo." Inside the second bedroom was a portrait of Mickey Boardman, the stylish former editorial director of Paper magazine; one of Keion Kopper, a painter and poet from Brooklyn, depicted with do-rag and paintbrush; and one of a ballerina, Georgia Duisenberg, posing in hot-pink toe shoes. Many of the people Dressner has painted have a special skill—fencing, the piano—and Dressner had decided to turn his exhibition into a talent show of sorts. Rosa is a dancer. "He's very versatile," Dressner said.

He headed out to Washington Square Park in search of inspiration, pushing his supplies in a custom-built cart: the chassis of an adult tricycle soldered to a laundry basket from the Container Store. In the park, he unfurled a blue-and-white beach umbrella, tied an apron around his waist, and waited. Soon, he had a subject in his sights: Brian Boyle, who had been lounging in the grass with his girlfriend, Salma Aceves.

"I'm a lawyer and a mental-health counsellor," Boyle said, as Dressner began to sketch the contours of his head in blue acrylics. "I'm a mental-health counsellor for lawyers. Lawyers are consistently in the top twenty suicide by profession."

"I might hit you up after this," Dressner said.

In dabs of electric yellow and lime green, a face started to take shape. "By the time Brian sees it, I will actually like it," Dressner said. "But that moment lasts for literally the last two seconds of the entire process, because I will hate it until then. "

A flock of spectators peered over Dressner's shoulder. "Really beautiful," one said.

At last, the big reveal. Aceves clapped her hands. "I love it!" Boyle said. Dressner gave him the portrait to take home, then started packing up. Did he ever miss the law? "I do like the routine of going somewhere, and saying hi to your colleagues, and the cafeteria," he said. "But this is much more fulfilling."