There’s something dodgy about portrait artists, and that’s part of their allure. One way or another, they need faces. Often, they steal them and hope nobody complains. At times, they entice volunteers by appealing to their arrogance or cluelessness. Other portraitists pride themselves on treating their subjects well—befriending them, learning about them—but even a subject who feels seen may not understand exactly what she’s getting into (how many people know how they look?), and, if she is satisfied with the result, she is lucky. It’s the artist’s way that counts, not hers.

Not everyone agrees—if anything, there seems to be a law that all great portraitists must be praised for their empathy. (Even Diane Arbus, who referred to the people she photographed as “freaks,” is now described as a champion of body positivity.) There’s something defensive about this, perhaps related to the intrinsic strangeness, so common that we forget, of looking at faces that can’t look back. The more we flatter portrait makers for their virtue, the better we portrait viewers get to feel about our ogling.

Henry Taylor, the subject of “Henry Taylor: B Side,” a new exhibition at the Whitney, is an empathetic portrait painter. So the exhibition insists, so Taylor has said, and so I’d agree, up to a point—the point, to be precise, where things start to get interesting. Taylor grew up in Oxnard, California, but has lived in Los Angeles for years, and sometimes seems to have painted everyone who’s spent any time there at all, from panhandlers and music moguls to his siblings and the Obamas. The richness of Black American community and the indignities of Black American life, in particular the violence of law enforcement, are his recurring themes. There’s also an undeniable strain of impishness and amoral weirdness in his work, though this show isn’t always sure how to handle it. After a friend of his, the artist Noah Davis, died of cancer, he painted the man as an adolescent (or a man trapped in an adolescent’s body), one eye blue and the other brown. His 2007 portrait of Eldridge Cleaver, modelled on James McNeill Whistler’s famous portrait of his mother, is a terrific prank: the macho activist who attacked James Baldwin for his dandyish effeminacy gets feminized. I don’t know if these are empathetic or ethical works; what I know is that they reward looking.

Taylor, sixty-five, is a more compelling artist than this exhibition suggests, and often a weaker one. The past few years have been kind to him—in June, he launched a collaboration with Louis Vuitton, and “B Side,” which was previously at the Museum of Contemporary Art in L.A., has received breathless reviews—but he got off to a slow start. For a decade, he worked as a psychiatric technician in a mental hospital, and he was nearly forty when he graduated from CalArts. In his work, there’s a palpable sense of making up for lost time; he rarely takes more than one sitting to finish a painting. This shoot-from-the-hip approach works best when he observes something small and strange in his subjects—the way, for example, the seated woman in “Resting” (2011) holds her right wrist in her left hand, creating a little fortress around herself. The posture of the man sitting next to her is as open as hers is closed, and neither of them acknowledges the teeming prison yard in the distance. It took me a second visit to the Whitney to notice the third figure in the foreground, reclining behind the other two. Who is this? Are the woman and man (Taylor’s niece and nephew) leaning against a couch, or a body? In a painting preoccupied with prisons literal and otherwise, the incoherence isn’t merely odd but disturbing. It rings in your ears.

Were “B Side” bursting with paintings like this, it might have been one of the better shows of 2023. Much of the time, however, Taylor doesn’t really paint paintings at all; he paints faces and occupies the rest of each canvas with bright, dead space. Most of “Portrait of Steve Cannon” (2013) is devoted to dribbles and scratches not quite filling the emptiness—they’re the visual equivalents of “um”s and “like”s—and his faces aren’t always much livelier. It’s striking, given Taylor’s reputation, how often he smothers his sitters’ personalities with his own stylistic mannerisms (asymmetrical eyes, flat frontal views, chunky lines). A good portrait needn’t be an empathetic one, but it should at least seem to discover something in its subject—the style should be rich and surprising enough to suggest a spark of life. Look at Taylor’s portraits of the composer George Acogny or the artist Andrea Bowers, and then at his portraits of Kahlil Joseph or Jay-Z or Deana Lawson. In the first group, there’s a tautness in the expressions and a specificity in the gazes: someone’s in there. In the second, I sense no spark, just a prolific artist’s eagerness to move on to the next thing.

This show is a good reminder of the difference between upsetting art and unsettling art. It is deeply upsetting to look at the strapping, utterly vulnerable inmate in “Warning shots not required” (2011), though the title is more powerful than the figure, and a nearby wall, covered in photographs of beaming Black men and women unaware that they will be killed, is more powerful than either. “THE TIMES THAY AINT A CHANGING, FAST ENOUGH!” (2017), a huge painting of Philando Castile dead in his car, his eyes still open, betrays some of Taylor’s weaknesses: slack composition, size used as a shortcut to gravitas. It’s also one of the most upsetting paintings I know, a memorial to a young man shot five times for the crime of obeying a police officer. It stings. I’m trying to imagine a similar work of art that wouldn’t.

When I saw “THE TIMES,” I thought of “Black Painting,” Kerry James Marshall’s tranquil, unsettling image of the Black Panther Fred Hampton in bed with a pregnant Akua Njeri. It’s an image as dark and dim as Taylor’s is bright, as slow-acting as Taylor’s is immediate. (If you can make sense of it in less than a minute, your eyesight is better than mine.) Njeri seems to be trying to listen to something, which we know to be the sounds of cops about to murder her fiancé in his sleep. Yet because the violence resides entirely in our minds, we’re denied the warm consolation of catharsis—and who says we deserve it? To the extent that we see and identify with the two figures at all, we’re forced to assume a perspective horrifically close to that of Hampton’s killers, blundering around a strange room in search of bodies. To look at them is to lurk; to empathize is to intrude—standing before “Black Painting,” you wonder how anyone could have thought life was simpler.

At his finest, Taylor doesn’t. The most illuminating works in this show are a series of sketches he made while working at the mental hospital. The days were long, and drawing was a way of passing the time when he wasn’t administering medication or giving shots. Patients could be agitated, or violent; in some of the sketches, they’re unconscious, or trapped in five-point restraints, their eyes covered. You can interpret these images as studies in compassion—the show certainly does—but imagine Taylor on the job, pencil and paper in hand, staring at people who can’t stare back, and maybe you’ll agree that the portraits evince something closer to fascination, the kind of unquenchable compulsion that inspires someone to make thousands of drawings and paintings, often many a day, for decades.

You can feel the same compulsion coursing through “i’m yours” (2015), Taylor’s portrait of himself and his children. Almost half of the canvas is dedicated to Taylor’s face. His son’s is tinier, and his daughter’s presence in the upper-left corner seems like an afterthought, which, according to Taylor, it was. The two small portraits are as slapdash as the self-portrait is lushly layered; you could stare at Taylor’s face for an hour and still find new colors, and his own stare seems too deep and too hungry to be satisfied. This may strike you as a little impolite—aren’t parents supposed to lavish more attention on their kids than on themselves?—but, then, art has no obligation to behave itself. There are no purely moral ways of looking, nor purely immoral ones. There is only looking, and the artists who do it because they’d rather die than not. ♦