Artist Adam J. O’Day, who won last summer’s Portrait of a City contest with his piece Transit, is Boston’s own, modern Monet—he’s a landscape painter, he’s a rule breaker, and he’s got a beard that the 19th century, French Impressionist himself would undoubtedly envy.

Often depicting local scenes with a gritty flair, O’Day’s work drips with color. In his pieces, red and blue clouds hang behind Kenmore’s Citgo sign, pastels reflect the city’s skyline in the Charles River, and the brownstones of Newbury Street dress themselves in tie-dye. O’Day’s depictions of Boston go beyond what is there, beyond what he actually sees. They place emotion above reality. They represent what he feels. “I think it’s important to get down to the nitty gritty of a place and express that through color,” O’Day said. “It’s a more interesting vibe.”

O’Day’s impressionistic style was born, almost literally, when he painted a dream-like portrait of a baby for his introductory oil painting class in college. The picture, which he still has even a decade later, was drippy, wet, and messy. It didn’t adhere to the rules and methods that some of his professors said he had to follow, and he didn’t quite care. He just let it flow.

O’Day always had a love for art—and an odd obsession with black crayons—as a kid, but, as he got older, he wasn’t sure whether he should pursue his passion professionally. After high school, he went to Lesley University (then AIB), graduating with a degree in graphic design and illustration, which helped him get a job in the navy doing drafting work. O’Day spent nearly five years there. He’d draw up and program virtual blueprints during the day and then paint at night.

“The job was so structured that when I got out, the art would come easily,” O’Day said, “because I had this other side I needed to express.”

Eventually, O’Day’s wife gave him the push he needed, encouraging him to place his creative pursuits over his commercial ones. O’Day’s pieces have appeared in over 100 exhibitions—80 of which were in Boston—since the beginning of his painting career. His next projects, which he’s preparing for in his Abington studio, include an abstract, geometric show in Salem, called “Other,” as well as a July show in Provincetown named after and based on the Portrait of a City competition he won in 2014. O’Day, a fan of Calvin & Hobbes and Hunter S. Thompson, said that a display at the Hynes Convention Center this September could be a possibility, too.

Landing his paintings in galleries like these didn’t happen overnight, though, O’Day said. It took years of hosting open studios and hanging his work on restaurant walls to get his name out there. Mounted in places like at Christopher’s in Cambridge and at Tasty Burger near Fenway, O’Day’s art began to reach more and more people—including NHL hockey player Shawn Thornton, who actually yanked one of his paintings right off the wall of Citizen’s Pub after his wife declared that she had to have it.

“He never reached out to me about what he did with it,” O’Day said, “but it’s kind of cool knowing that a Boston Bruin has some of my artwork.” 

While O’Day has been commissioned to paint the “quintessential views” of Boston, New York, and other cities around the world for the past decade or so, the Tennessee native said that he’s been intent on capturing scenes other than major landmarks. To him, a narrow, puddled alley in Cape Cod and a row of old houses in Allston could be as exciting as the Prudential Center or the Eiffel Tower.

O’Day’s macro to micro perspective shift isn’t just confined to his art. He’s been focusing on appreciating the small things in his life, too, spending time with his 7-month-old daughter Penelope, keeping in touch with his high school art teacher via Facebook, jamming out on his drums, and watching his favorite movies from his VHS collection. To O’Day, those little things aren’t actually little at all. They’re huge—because it’s those little things, he said, that make up the biggest and brightest of pictures.