For most of his 50-year career, Richard Estes has painted a subject that he doesn’t seem to like much: New York City. A shy loner from Evanston, Ill., Estes moved to New York in 1958, working as a freelance illustrator before finding his voice as an artist. Around 1967, Estes began translating photographs of the city’s banal storefronts and corridors into hard-edged, detailed paintings.

The resulting body of work is visually arresting, but often feels chilly and unglamorous—as if the artist is unable to identify with his surroundings. “I don’t enjoy looking at the things I paint, so why should you enjoy it?” he said in a 1972 interview with Art in America magazine. “I’m not trying to make propaganda for New York or anything. I think I would tear down most of the places I paint.”

Estes was a pioneer of photorealism, a late ’60s movement characterized by airtight renderings of gleaming countertops, chrome trim on fast cars, and glossy windows and mirrors. While the movement’s heavy reliance on the camera as a tool for composition might seem forward-looking, Estes’s attitudes were actually fairly conservative. Sure, he rejected the abstraction, expressive brushwork, and pathos of the previous generation of modernists, but Estes wasn’t too keen about his pop-art peers, either. “The trouble with pop art is that it made too much comment,” he said in that same interview. “Once you get the message, you lose interest.”

It’s tempting to think that this dissonance between Estes, his immediate surroundings, and the contemporary art world might somehow explain why his oeuvre has been neglected. “Richard Estes’ Realism” is the artist’s first full career survey in the U.S. since 1978, despite his fierce work ethic; he’s produced many new paintings in the three decades since. Organized by the Portland Museum of Art in Maine and the Smithsonian American Art Museum with independent curator Patterson Sims, the show features 46 paintings depicting not just New York, but also Tokyo, London, and Paris, and even natural landscapes.

“Realism” demonstrates that although Estes may be a stubborn, solitary cuss, his focus on technical and formal issues has yielded a muscular, unified body of work. His paintings masterfully depict a flattened, airless world full of disorienting reflections and curious jumps in scale, effectively capturing the feeling of being lost and alone in a land of skyscrapers.

“Horn and Hardart Automat” (1967) is an early transitional piece that contains the seeds of Estes’ mature style. A man sits at a table behind a large plate glass window. His eyes are a single dark stripe; the rest of his face consists of a few patches of light and dark brown and an oily highlight on his forehead. Estes seems to regard him with all of the interest and empathy one might have for a lumpy potato.

His body is crammed into the lower left-hand corner of the composition to make room for Estes’s true subject: the building façades across the street, reflected in the massive automat window. Estes renders this ghost image with a full range of tonal contrasts, making it appear closer to the viewer than any of the directly observed objects in the picture. Bright geometric patches of translucent, loosely applied color form thin stripes in the left and right-hand margins, framing the giant sea of reflections and exerting a curious visual pressure. The city seems to consume our vision entirely, transforming everything and everyone that passes through it.

This compositional vertigo follows Estes throughout his career, reaching some sort of apotheosis in 1980 with “Waverly Place.” This roughly 36” x 80” painting stretches beyond the viewer’s peripheral vision, encompassing 180 degrees in an impossible panorama. Massive scope is paired with crystalline clarity: Each tiny brick and fire escape in every distant brownstone is painstakingly enumerated.

“Waverly Place” reveals exactly how Estes works with photos. Photorealists like Robert Bechtle typically employ projectors to trace the contours of a photograph onto canvas. Estes is far more old-fashioned, never resorting to tracing, often stitching together information from multiple photos of the same subject. As a result, marginal distortions—the way objects can appear stretched at the edges of a snapshot—are typically absent in Estes’s world. The artist once joked that he is really a plein air painter, except that instead of communing with nature, he immerses himself in prints.

Estes takes many photos early on Sunday mornings to avoid people. One imagines that “Bridal Accessories” (1975) must depict a very early hour indeed: Densely packed rows of darkened shops frame one luminous window, filled with disembodied veiled heads. The street is completely empty, save for a single beer can, incongruously lying in the gutter in the very middle of the picture. Even Estes’ trash seems fussy and manipulated.

This gridded, melancholic piece echoes Edward Hopper’s Depression-era painting of shuttered shops—titled, of course, “Early Sunday Morning.” Older American realists like Hopper and Charles Sheeler are closer to Estes in spirit and form than most of his photorealist contemporaries; the artist typically reaches back even further to name painters he understands. “Estes feels that his major artistic influences skip back more than a century,” Sims writes in the show’s catalog. “For him, modern and contemporary art offer no painters equal to Edgar Degas, Édouard Manet, or earlier masters like Velázquez.”

In recent years, Estes seems to be trying to reaffirm the figure, and the results can feel second-hand and clumsy. “Checkout” (2012) depicts a busy market—decked out with mirrors and glass, of course—on Valentine’s Day. The shoppers and clerks here are uncharacteristically large and cartoonish. A red heart intersects the face of a woman in a fuzzy pink hat, making her look almost cross-eyed. It’s an odd mismatch between bleak flatness and goofy kitsch.

And then there are the late landscapes, tonal pieces with lots of buzzing, meandering texture. “Water Taxi, Mount Desert” (1999) includes a giant girl riding on a boat. The girl’s hand seems shrunken, improperly foreshortened. Out in nature, Estes’s command of light and atmospheric effects remains evident, but his attempts to show great spatial depths without hard angles and reflections often fall flat.

Through the exhibition, Estes emerges as a traditionalist, concerned with tools and techniques and dismissive of the critical discourse of his peers. His skepticism of his hometown—New York, center of the art world—has ended up being the heart of his work. When he takes on other subjects, Estes is still a master of his medium, but that edgy tension between the man and his surroundings is absent. “Making a picture out of something is a way of putting oneself in control of it, like the cavemen and their pictures of wild animals,” Estes explained in the catalog for the 1968 exhibition “Realism Now.” “Maybe making a picture of your environment is a way of coping with it.”

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Due to a reporting error, an earlier version of this review listed the Portland Museum of Art and Patterson Sims as the sole organizers of the show. In fact, the Smithsonian American Art Museum was a co-organizer.