Money, I’ve heard, cannot buy happiness. And through the 1980s, Tina Barney’s darkly witty pictures of her insular upper-class milieu gave a diabolically cheerful endorsement of that tried-and-true claim. These now-classic half-staged, half-spontaneous shots are a visual tone poem of WASP privilege and icy repression—a hot mess of sunburned boredom, simpering awkwardness, and vacant stares. This show, the artist’s first at Paul Kasmin Gallery, included eleven works that span forty years and that range from the iconic (Mark, Amy and Tara, 1983) to the newer and lesser known.

Among the earliest pieces here was The Reception, 1985—one of my favorite on view. This killer shot features a young gentleman who looks plucked straight from the cast of American Psycho lounging in an armchair with his finger on his chin. He gazes smugly at the woman beside him, who has spotted something outside the frame. She looks terribly displeased, her face twisted into a savage, avian stare. This vaguely ridiculous, somewhat unnerving moment would be frightening enough, but there is another guest in the scene: Picasso’s woozy, blue-period Angel Fernandez de Soto, 1903, hanging on opulent oak-paneled walls. Though the conspicuous domestic display of trophy art may bring to mind the work of Louise Lawler—namely, her contemporaneous deadpan photos of Mr. and Mrs. Burton Tremaine’s collection entombed at their Connecticut home—here the effect is rather different. The painting’s watery gaze—knowing, wry, languid—comes alive, weirdly mirroring the expression of the young man. It’s a funny, disorienting coincidence and saves the picture from serving as some ham-fisted moralizing tale about rich people being mean.

Other works in the show give a sense of Barney’s range in the years that followed, evinced in such pieces as, say, The Wheelbarrow, 2005, from her series “Small Towns,” 2005–12, for which she documented the industry and social rituals of rural New England, and The Bust, 2003, from the “The Europeans,” 1996–2004. (Less successful, in my view, is The Limo, 2006, portraying two male models; it looks too slick, too cool, too clean.) Barney’s respected editorial work was represented in the form of the amazing Mr. and Mrs. Leo Castelli, 1998, for W magazine. In that image, the legendary art dealer and his wife pose in their spartan home, as she tosses her hair back to mimic, almost exactly, the undulating mane in the Roy Lichtenstein sculpture beside her. As in The Reception, life imitates art in an uncanny, stylish flash.

“I’m documenting . . . a way of life that I don’t think might ever happen again in America,” Barney once said of her photographs. And the pictures do indeed feel like relics from the past. Over the last thirty-some years, the cartography of wealth and global power has shifted. The rich have gotten richer, and capital itself has become more diffuse and vaporous, somehow harder to grasp. The idea that wealth can be distilled into a social group, a set of tastes, or even “taste” itself, the idea that wealth can even be pictured, now feels like a fiction, if it were ever true at all. Barney’s works, these freakish comedies of manners, herald the end of a different age.

—Lloyd Wise