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Gustave Caillebotte gets no respect. In 1876, at the age of 27, the Paris-born painter was invited to join the Impressionists; he went on to help organize and participate in five of the group’s eight official exhibitions. Yet he’s mostly remembered as the group’s doomed rich dilettante—the guy who paid Monet’s rent, collected his friends’ art, and dropped dead in his mid-forties while puttering around in his garden.

True, Caillebotte didn’t quite fit in with his contemporaries. Like Degas, he used black in his palette, and didn’t share the Impressionists’ broken contours and bright complementary colors. He was a studio painter, more suited to constructing deep-focus images of people wandering city streets than sketching hazy, flattened landscapes en plein air. And he eventually retreated from art, leaving Paris in 1888 to focus on collecting stamps, yachting, and tending to his estate on the Seine at Petit Gennevilliers near Argenteuil.

Caillebotte may have inadvertently engineered his own obscurity. When he died in 1894, the French government accepted a gift of 40 pieces from his collection. That group included Monet’s “Interior of the St. Lazare Train Station” (1877) and Renoir’s “Ball at the Moulin de la Galette” (1876), both now at the Musée d’Orsay in Paris. In his will, Caillebotte insisted that these paintings remain on public view—thereby helping to establish his friends’ future legacies. Meanwhile, most of his own paintings stayed in the hands of his family and out of circulation until the 1950s.

“Gustave Caillebotte: The Painter’s Eye” is the latest effort to rehabilitate Caillebotte’s reputation as a painter, not just a benefactor. On view at the National Gallery of Art through October 4, the show is a medium-sized greatest hits collection, bringing together 57 of Caillebotte’s works.

Why only 57? As curators Mary Morton and George Shackleford explain in the show’s catalogue: “Of the some 500 paintings in his known oeuvre, only a fraction warrant the attention of a major exhibition.” Even Caillebotte’s champions still have their doubts.

The exhibition largely breaks down Caillebotte’s work by genre. His best-loved cityscapes appear in the first three rooms; the back galleries contain less-familiar still-lifes, a couple of clumsy yet compelling nudes, and landscapes that the curators must regard as subpar. “Dozens of views of riverbanks, of sailboats at anchor, of seaside cliffs, stands of trees, or orchards in bloom were executed over the course of the second half of [the 1880s],” Shackleford writes in his essay, “seemingly without much aim and without much conviction.” So much for the show’s seventh room, devoted to boats, flowers, and fields.

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Caillebotte’s paintings reflect his privilege. His breakthrough piece from the April 1876 Impressionist exhibition, “The Floor Scrapers” (1875), depicts shirtless workmen finishing the floors of his custom-built studio—paid for by his father. The subject is a product of Caillebotte’s early, more conventional ambitions: He trained at the École des Beaux-Arts in Paris and was interested in the classical male nude.

Yet this is not a polite, academic painting. The three figures are depicted kneeling, their elongated, sinewy arms and bony torsos rendered in wan shades of yellow and brown. Light from a window bounces off gilt wall accents and limns the workers’ straining muscles. The viewer’s relationship to these laborers is complicated by the picture’s perspective: The floor appears to tilt downward, suggesting that the artist was standing on a ladder or chair, towering over his subjects.

These two elements—wealthy and working-class life intersecting, and odd, stagey pictorial spaces—typify Caillebotte’s best paintings. In “On the Pont de l’Europe” (1876-7), for example, three men stand on a bridge one gray, chilly morning. One wears a bowler hat and a workingman’s blue jacket; the other two wear silk top hats and long coats. Their faces are all turned away from the viewer; two stand side-by-side, watching the Gare Saint-Lazare railroad yards.

Yet the yards are mostly hidden from the viewer: The bridge’s thick, criss-crossing girders and railings fill the painting and fragment the pale city skyline. The result is a view of Paris radically altered by new construction and technology—almost closer in spirit to the New Vision photography that would appear between the two world wars than to Monet’s painterly atmospherics or Pisarro’s peasant reveries.

Caillebotte’s images frequently beg comparisons with photography. Take the snapshot-like cropping and jumps in scale of “Interior, a Woman Reading” (1880). A woman with a newspaper, occupying nearly two-thirds of the canvas, is cropped above the waist; the head of a comically much smaller man, lying on a couch deep in the background, intersects with her knuckles. These figures share a domestic space—but the picture’s discontinuities suggest they are psychologically isolated.

And then there’s “Paris Street, Rainy Day” (1877), a seven-by-nine-foot image of the eighth arrondissement that’s almost certainly based on photos. A bright green lamppost splits the picture in half; while the left side draws the viewer’s eye far away, to clumps of tiny, interchangeable pedestrians, the right side is cramped and close-up. A man and a woman appear ready to stroll out of the painting arm-in-arm as they squeeze past a man with his back to the viewer. This third figure seems like an afterthought, jammed into the margin and radically cropped.

Yet this tension is precisely what makes the painting exceptional, reflecting the excitement, anxiety, and loneliness of modern cities at the end of the 19th century. With paintings like this, Caillebotte seems to answer Baudelaire’s 1863 essay, “The Painter of Modern Life,” which calls on artists to address “the ephemeral, the fugitive, the contingent.”

If only he’d kept courting that tension. The show’s later rooms reveal an artist playing against his strengths. Caillebotte was not really a colorist; he did better when he focused on line, perspective, and tonal contrasts. Yet in the back rooms of the show, the artist spends his later years painting sun-dappled fields and skiffs on the water in a manner that recalls Monet without ever matching him.

If Caillebotte hadn’t abandoned his own pictorial ideas, maybe “The Painter’s Eye” would feel like a sampling of an artistic oeuvre worth exploring in depth. Instead, even at a mere 57 paintings, the show feels bloated—it’s a half-great show. Caillebotte’s real problem wasn’t that he didn’t fit in with the Impressionists, but that he desperately wanted to.

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