Queen Latifah Redefined Being a Multihyphenate — and Made It Look Easy

In our 2023 Greats issue, out Oct. 22, T celebrates four talents across music, film, art and fashion whose careers are a master class in curiosity, composure and defiance.

EVEN BEFORE heading from the Fondazione Prada, a contemporary art complex housed in an old distillery on the southeastern edge of Milan, to Miuccia Prada’s office about a mile away, I’m reminded of her towering presence everywhere I look. A docent, dressed in a black Prada uniform, shepherds a pair of tourists, both carrying Prada handbags, into a screening of “Four Unloved Women, Adrift on a Purposeless Sea, Experience the Ecstasy of Dissection,” a short film by the Canadian director David Cronenberg accompanied by a wunderkammer of 18th-century anatomical wax sculptures. Once outside, I pass an abandoned rail yard and billboards for two other Fondazione exhibitions: a permanent re-creation of the home studio in Switzerland where Jean-Luc Godard edited his final movie, and a survey of videos, photographs and other works by the New York-based artist Dara Birnbaum on view at the Osservatorio, a satellite venue overlooking Galleria Vittorio Emanuele II, the shopping arcade where Mario Prada, Miuccia’s maternal grandfather, opened the brand’s first store in 1913. Down another few blocks, an old woman in a pair of Prada sunglasses walks by with her dog.

At 75, Mrs. Prada, as she’s known to strangers and friends alike, is perhaps the most peculiar and certainly the most innovative fashion designer of her generation. In 1975, she took over her family’s leather goods business. Two years later, she met her future husband, Patrizio Bertelli, now 77 and the chairman of the Prada Group, with whom she began building a global empire. (In 2022, the company’s annual revenue was $4.5 billion.) In addition to Prada, the couple has ownership stakes in Miu Miu, which might be described as Prada’s unruly niece; the footwear brands Church’s and Car Shoe; and the Pasticceria Marchesi pastry shops. (As of last year, they can also claim some of those dusty train tracks: Prada Holding, which owns 80 percent of the Prada Group and is controlled by the Prada family, is one of three entities that acquired the plot of disused land for roughly $190 million to convert it into a park, housing, offices and the Olympic Village for the 2026 Winter Games.)

Those with no interest in fashion have at least seen the house’s triangular logo and know Prada’s name, whether through movies (in 1999’s teen comedy “10 Things I Hate About You,” a student explains, “There’s a difference between like and love. Because I like my Skechers, but I love my Prada backpack”) and TV shows (in a 2019 episode of “The Simpsons,” Homer relieves himself behind “Prada Marfa,” a replica of a Prada store created in 2005 near Marfa, Texas, by the artists Elmgreen & Dragset), books (Lauren Weisberger’s 2003 novel, “The Devil Wears Prada,” which became a hit film) or music (Beyoncé, Doja Cat and Drake have all name-checked the brand). And yet no matter how far and wide her influence extends, Prada hasn’t made it easy to know her, which is, like everything she does, deliberate.

Upon my arrival at the Prada headquarters, a set of stern buildings that occupy approximately 108,000 square feet, I’m confronted by my potential expulsion: the notorious stainless-steel slide connecting the designer’s third-floor work space to the courtyard. The German artist Carsten Höller, who installed it in 2000, says it was intended to help her “leave quickly, traveling through the floor under her office to have a glance at the people working there and then land right where her chauffeur is waiting.” But, he adds, “It’s also a good way to get rid of people.”

INTERVIEWING Miuccia Prada, unlike talking to her, can be a tricky enterprise. From her desk in an austere room with white walls and poured concrete floors — what might be mistaken for an operating theater, were it not for the Gerhard Richter painting and a silver bar cart stacked with cookies — she seems to begin every other sentence with, “Between us. …” She is 5-foot-4, with hazel eyes and wavy blond hair, and has the measured confidence of someone who’s about to deliver the bad news first. Despite her warmth and frequent laughter, she also seems ready, maybe even eager, to spar. She, too, is recording the conversation and taking notes. When I ask what she does to relax, her answer is “no.”

Although she’s less inscrutable than her intellectual peers — Rei Kawakubo rarely speaks to journalists; Martin Margiela never has — she’s certainly not as flamboyant as Domenico Dolce and Stefano Gabbana or Donatella Versace, flashier designers from the height of Italy’s sex-bomb era. And while she refuses to acknowledge personal achievements (“I leave it to other people to say what I did,” she says), she’s not above engaging in some mythmaking of her own: There’s a reason her last fragrance was called Paradoxe.

“If Harvard was a billionaire woman, it would be Miuccia Prada,” says the Italian artist Francesco Vezzoli, her close friend and frequent travel companion. The Belgian stylist Olivier Rizzo, who has worked with her since 2005, tells me she’s changed the way we dress and think about clothing “on every possible level on all levels forever and ever.” She’s “a challenger,” says the Italian creative director Ferdinando Verderi, who has consulted for the brand since 2019. “She’d even challenge the idea of being a challenger.” The American artist Theaster Gates, chairman of Prada’s Diversity and Inclusion Advisory Council, says, “If you’re trying to get a character sketch of Miuccia, she’s [expletive] sincere. And sincerity is better than being right all the time.” The actress Uma Thurman, who developed a relationship with the designer after wearing a lilac Prada gown to the 1995 Oscars, likens her to “a growing tree, letting herself have new barks,” while the musician Frank Ocean, who was photographed for the brand’s spring 2020 campaign, draws an analogy between her “tone,” he says — “how she resonates, basically” — and the meditative sound of om. The Italian gallerist Carla Sozzani, the founder of the 10 Corso Como concept store in Milan, who remembers “applauding like children” with her friend at runway shows in the 1970s, says, “Some people are more reserved when they’re in public. I’m not saying she’s another person [in private], but she’s more open.”

Though that might be accurate, it’s also true that no other female designer has produced such a robust body of autobiographical work. (The punk iconoclast Vivienne Westwood came closest; one screamed, the other sublimates.) Prada may not seem especially eager to reveal herself in conversation, but she’s always communicated more freely through her clothes, which make the case against what she calls “cliché beauty” and “the isolation of fashion.” Instead, she has grounded her work in the idea of a uniform — she’s as likely to find inspiration in nuns as in sex workers — craving the proximity to what she considers more noble, or at least more honest, professions. If Yves Saint Laurent created a wardrobe for the modern woman in the 1960s, then Prada, a champion of bad taste and the jolie laide, gave her permission to be weird and mercurial; to be, in a sense, her. “One of the reasons I started doing clothes was because I couldn’t find anything to wear,” she says.

It’s almost as if she comes up with her designs because they could be — and maybe so that they will be — deemed unflattering or unsexy. “She’s always looking for something that’s unseen,” says the Russian stylist Lotta Volkova, who consults for Miu Miu, which was established in 1993 as a less intellectualized and slightly less expensive alternative to Prada. Earlier this year, at Miu Miu’s fall 2023 show in Paris, some of the models wore underwear as outerwear; many had frizzy hair and cowlicks. The British hairstylist Guido Palau, who contributed to his first Prada show in 2004, says that the designer wanted the models to look as if they’d been caught in a gust of wind. A few seasons earlier, for Miu Miu’s spring 2022 collection, Prada delivered raw-edge chino micro-miniskirts belted below the hip bone. “Sometimes it’s the breasts, sometimes it’s the back,” she says about fashion’s obsession with the female form. “What wasn’t trendy was the lower waist, so I said, ‘Let’s make it as low as possible.’” The garment, which was her way of poking fun at things like fashion magazines, showed up in all of them.

“It’s a lot about being against something,” she says. Prada’s spring 1996 collection, its first of many “ugly chic” offerings, incorporated jarring colors (rust, mustard and “bile green,” as one critic would call it) and banal prints (later described as “Formica”), a response to the relentless sex appeal at the time of brands like Gucci, then stewarded by Tom Ford. But for fall 2002, to avoid being reduced to her somewhat prim, vaguely retro aesthetic — which had, however improbably, come to define Italian style as much as an Armani suit — she released what became known as a “porno chic” collection of transparent PVC coats and knee-high black leather boots. “Clothes were never about doing clothes,” she says. “It’s about living different parts of your personality.”

PRADA STILL resides in the Milanese apartment where she and her two older siblings, Marina and Alberto, grew up. In 1958, her mother, Luisa Prada — a “beautiful, elegant lady,” says Sozzani — took over Miuccia’s grandfather’s shop, which she then ran for nearly 20 years. Her father, Luigi Bianchi, owned a company that made putting-green mowers. The details of that period bore her. “Nothing bad, nothing good,” she says. But she sits a bit straighter when it comes to her teenage years. “That,” she says, “was the big political moment.”

While enrolled at the University of Milan (where she also earned a Ph.D. in political science), Miu Miu, as she’d been known to her family since childhood, joined the youth-led demonstrations and worker strikes that became referred to across Europe as the protests of 1968 (an era that in Italy would morph into the violent Years of Lead). “I really believed we could transform the world,” says Prada, who also studied mime for five years at Milan’s Piccolo Teatro. When she was a young member of the Union of Italian Women, a feminist offshoot of the Communist Party, the films of Godard and Pier Paolo Pasolini, both avowed Marxists then, greatly influenced her; fashion, on the other hand, was considered an inconsequential pursuit. “I was ashamed,” she says. “But nevertheless, I pursued it because I liked it.”

She was also compelled by a sense of duty. “I started kind of against my will,” she admits. “Somehow it just happened.” A couple of years after taking control of the company, she attended a trade show where she met Bertelli, who had recently given up on an engineering degree to run a leather factory that manufactured belts and bags. “We started as competition, and we’re still competing,” she says fondly. “In the end, that’s something that keeps us together.”

People tend to speak about Bertelli, a shrewd industrialist who collects vintage sports cars and sails several yachts — and with whom Prada has two children, Lorenzo Bertelli, 35, the Prada Group’s head of corporate social responsibility, and Giulio Bertelli, 33, a sailboat racer — as if they were describing a movie villain they’re secretly rooting for. “He has amazing charm,” says Sozzani. “You have to love Bertelli. Or you don’t.” Francesco Risso, Marni’s creative director and a member of Prada’s design team for eight years until 2016, recalls “the most theatrical fights” between the couple. “It didn’t feel unhealthy ever, but it felt like fireworks, that’s for sure,” he says. But as much as they might bicker — he was initially against, for example, her decision to do a sneaker collaboration; she released it anyway — Bertelli is also quite protective of her: Seldom does one approach Prada about a project without going through him first.

“If I hadn’t met my husband, I don’t know if I would’ve done this job,” says Prada, who set out opening factories with Bertelli and creating an international brand for “good women, bad women — the richness of all these different people.” The designer, who has no formal training and doesn’t sketch, begins each collection with concepts rather than silhouettes. One of her earliest pieces, in 1984, was a statement of intent: a modest backpack made not from crocodile or calfskin but black Pocono, an army-grade nylon more commonly associated at the time with parachutes than with purses. Nearly 40 years later, that utilitarian bag and its many iterations remain unlikely objects of desire. “Any bourgeois subject that I approached,” she says, “I always wanted to destroy it.” (Well, maybe not any bourgeois subject: “You shouldn’t eat, you shouldn’t drink, you should just work and work and work,” Risso recalls Prada telling him at one of his first staff meetings. “I could see that she was trying to push me to be better.”)

With the 1988 debut of her ready-to-wear line — some models came out in black and brown jackets inspired by men’s tailoring, others in hot pink dresses with 1950s silhouettes; almost all of them in flats — she introduced house codes that now include specific garments and accessories (knee-length skirts, bucket hats) and signature styles (geometric prints, color blocking). It’s often said that she and her trusted design director, Fabio Zambernardi (who is leaving the brand this month after more than three decades), determine the trends one season that others follow the next, which, though true, is incomplete; the clothes are only one part of it. At some point, it became almost obligatory for luxury brands to mount cultural, educational or philanthropic initiatives. But back then, she was the only one. “Basically, now every fashion house is a cultural platform,” says Vezzoli. “Bottega Veneta does a show with Gaetano Pesce chairs and Gaetano Pesce becomes the most sought-after Italian designer. Saint Laurent produces a movie for Pedro Almodóvar. But Prada did it 30 years ago.”

The Dutch architect Rem Koolhaas, whose research and design studio, AMO, has created the environments for every Prada show since 2004, says that each season the conversation starts with a word or two to “trigger intentions.” The prompts for the spring 2024 men’s presentation, which featured curtains of slime dripping from the ceiling down to an industrial steel grate on the floor — the cascading goo also made an appearance at September’s spring 2024 women’s show — were “creepy,” “flesh and skin” and “organic minimalism.” James Jean, a Taiwanese American painter who in 2007 designed the wallpaper for the brand’s SoHo store (his drawings of fantastical creatures and flowers were later printed on Art Nouveau-inspired skirts, trousers and bags for the spring 2008 collection), recalls their project beginning with three adjectives: “romantic,” “nonlinear” and “surreal.” The French sound artist Frédéric Sanchez, who has scored most Prada shows since the mid-90s, was, in a similar way, also creating for an idea of clothes rather than a finished garment. “With Margiela,” says Sanchez about his other longtime collaborator, “it was very physical”; sometimes they’d even repeat the same soundtrack season after season. His experience with Prada, he says, has been more “cerebral.”

It’s difficult to overstate how radically Prada has changed the landscape of contemporary luxury, a word she hates (“hate,” on the other hand, is one she really likes). These days, every reference seems to lead back to her, whether it’s a padded headband or a utility vest. Such a fixture is Prada on other designers’ mood boards that for her spring 2000 collection — which she referred to as “the ABC of fashion” — she paid homage not only to the work of Yves Saint Laurent but also, rather cheekily, to her own, in the form of reinterpreted cardigans and schoolboy shorts. And yet, what Prada has put out into the world feels more substantial and transgressive than a khaki crop top or the very notion of so-called quiet luxury — both things, mind you, that came from her. “It’s much cooler than being eccentric,” says the designer Marc Jacobs, a friend of hers. “With Mrs. Prada, it’s that thing of style with substance. It’s not just a shell that looks good.”

THE SOUL OF the Fondazione Prada is the Haunted House, a four-story gilded tower that contains work by the sculptors Robert Gober and Louise Bourgeois. On the second floor, there’s a Bourgeois installation called “Cell (Clothes)” (1996), in which pants and dresses appear to be trapped by a ring of wooden doors. On the top floor, there’s a 2010 wax sculpture by Gober of a child’s leg — almost Prada-like in a white sandal and matching ankle sock — weighed down by an anchor. There are no other clothes on this floor. Instead, Gober has installed a storm drain with water running beneath it. Under the metal bars, among the rocks and debris, sits an illuminated heart — discarded, but still beating.

Journalists inevitably like to bring up Prada’s political past, and not just because she likes to bring it up, too — though as a New Yorker article about her from 2004 notes, “in the ’60s it was almost a rite of passage for thousands of young middle-class Italians” to join the Communist Party. Prada, however, does seem to have a genuine need to reconcile the idealism of her youth with the choices she’s made since; and if ambivalence can be paralyzing, in her case it appears to have had the opposite effect. In 1993, her days of on-the-ground protest behind her — she’d long stopped handing out flyers at rallies — Prada and Bertelli created Milano Prada Arte, which later became the Fondazione Prada. It would give them a place to house their growing art collection but, for Prada, it also became a way to funnel her revolutionary spirit — and her money. “I tell my people in the Fondazione all the time to thank me,” she says. “I have to sell a lot of expensive handbags to run a museum.” (“Handbags are not art,” the British sculptor and painter Damien Hirst, a friend, recalls her saying. “Whereas when you meet other people, they’re constantly telling you that they are art, and you need 100.”)

From the beginning, Prada has been dutifully managing and scrutinizing every detail of the Fondazione’s programming — even showing up at Gober’s studio in Manhattan to convince him to contribute. Gober remembers that when she appeared on his doorstep, she said, “Like everything else, I have to do this myself!” (Her exit was equally quotable: When Gober sent her home with some books, she took one look at the tote bag he offered and said, “I’ll carry them.”) In 1999, she and Bertelli dropped in on Koolhaas at his studio in Rotterdam in the Netherlands. “They were bored with their stores,” Koolhaas says, and wanted him to oversee the construction of their New York flagship. “All my friends in the art world, or let’s say in the cultural sector, were extremely skeptical whether this would be a desirable collaboration,” he says. Koolhaas reimagined the Epicenter, as it’s called, on the site of what was once the Guggenheim Museum’s SoHo location, with an undulating wood floor and motorized hanging displays. In 2008, OMA, Koolhaas’s firm, was hired to design the Fondazione Prada.

Thirty years in, having worked tirelessly to earn her place in the art world, Prada has chosen to become the new director of the foundation. “My main track is [the Fondazione Prada],” she says. “I’d decided that I wanted to keep it separate from fashion. And no one knew — I never told anybody.” As she deliberates over what to say next, I’m reminded of something that the filmmaker Wes Anderson — who’s partnered with her on various film and art projects and who designed Bar Luce, the 1950s-style cafe at the Fondazione Prada — told me. “You quickly sense her vulnerability, which can sort of disappear from a person with such authority. I think without a bit of that, you can’t quite reach them. She can be fearless, but I don’t think she’s fearless,” he wrote in an email. “Maybe it’s because I’m getting older,” Prada continues, “but I want to reconcile my whole life and declare my job: I run the Fondazione.”

“She’s properly a patron,” says Hirst. “She really, genuinely sees art as something beneficial to other people.” And unlike almost every other collector who tells him they’re building a museum, he says, she actually did. The two were out to dinner one night when Hirst, who grew up working class, ordered caviar for the table. Prada sighed. “I really struggle to eat caviar,” she said. “Why would you struggle with that?” he recalls saying. “And she was like, ‘Oh, I was a communist.’”

FOR THE PAST few years, Miuccia Prada hasn’t had to do quite as much all by herself. In February 2020, just before the pandemic forced Italy into lockdown, the Belgian designer Raf Simons was announced as her co-creative director. The two of them, she said, would be jointly responsible for Prada’s women’s and men’s wear going forward. (She’s still the sole designer at Miu Miu; “When I change floors, I change mentalities,” she says.) The next day, Simons flew home to Antwerp. Upon his return to Milan that June, he mostly communicated with Prada through a screen.

It was a challenging start to an ambitious experiment. They both had simple reasons for wanting it to succeed. Prada was, as she puts it, “fed up working alone.” She was also, of course, planning her succession. “But they don’t want me to talk about that because they’re afraid it looks like I want to leave,” she says. “I don’t want to leave at all.” Simons, 55, had briefly worked for Prada and Bertelli before going to Dior and then Calvin Klein. (He was the creative director of Jil Sander from 2005 until 2012; the Prada Group sold the brand in 2006.) Following his two-year stint at Calvin Klein, a tumultuous period he describes as “hysteria,” he’d vowed to never again run someone else’s fashion brand.

“I’m not a stupid guy,” says Simons, who now lives in the Milanese apartment where the first Prada shows took place. When Bertelli reached out to set up a meeting, Simons says he knew they wouldn’t be discussing Church’s shoes. “It was more like, ‘Miuccia and I, this is our age, this is our reality,’” he recalls Bertelli saying. (In January, she and Bertelli stepped down as co-chief executive officers of the Prada Group and were replaced by Andrea Guerra, formerly the chief executive officer of the Luxottica eyewear conglomerate. Their son Lorenzo is expected to assume the role down the line.) Prada had wondered if Simons, who’d overseen his own cultish men’s wear brand for 24 years at that point (the line has since been discontinued), might want to look after the men’s collections. “But in three seconds,” says Prada, Simons suggested, “ ‘Why don’t we do the two together?’ And I immediately said, ‘Yes, why not.’”

In practice, they couldn’t be more different. Simons, whose cool aesthetic conveys restraint, would rather adhere to deadlines; she “loves to design today what needs to go on the runway tomorrow,” he says. And yet they share an aversion to traditional clothes. “It wasn’t a shock, like, ‘Oh my god, what a left-field choice,’” says Marc Jacobs. “If I were doing this movie, I’d have cast Raf.”

After years of having to make every decision on her own — even now, she’s thinking about the most recent installment of “Women’s Tales,” Miu Miu’s ongoing short film series, by the Croatian-born director Antoneta Alamat Kusijanović, and the Fondazione’s next two art shows — Prada is relieved to sit down with Simons and discuss the upcoming women’s collection. “Listen,” she says the day after the men’s show in June from her office, where she’s spent part of the morning reading the (good) reviews. “Every single moment you have to have ideas on so many things. Your brain evaporates.” Recently, she and Simons have resolved, at least temporarily, not to divulge the references or describe the characters in their collections with the world. “I decided that I didn’t want to tell stories anymore,” she says. “We’ll see how long it lasts.”

When it comes to how her own story is eventually told, she hopes not to have, as she puts it, “thrown my life out on superficial things.” Her goal, today, as it was in 1968, is to have done something good. “And deep down,” she says, “political.” But on my way out, I ask Prada if she ever wonders how her life might have looked had she not become a designer. “Always,” she says without hesitation. Then, as the elevator door begins to close between us, she smiles. “And never.”

THIS IS WHAT it means to command a room. Onscreen, the long-distance open-water swimmer Diana Nyad, as incarnated by Annette Bening in the new biopic “Nyad,” does not slink, sashay or flounce. Watching her walk, it seems absurd that such verbs should even exist. After all, this is a woman who, having retired from her athletic career on her 30th birthday, decided at 60 — an age at which many women find themselves shunted to the sidelines — to revive a dream of swimming the more than 100 miles from Havana to Key West, Fla., through waters regularly roiled by storms and teeming with sharks and swarms of venomous box jellyfish, whose stings have been likened to electrocution by those fortunate enough to survive them. There’s no strategic coyness to her stride, no adjustment to the wants of others. Bening’s Nyad moves through the world absolutely certain of her place in it. Which is not to say smoothly: Rather, she fully occupies her body, fully is her body, attenuated perhaps with the toll of age, but still a compact of muscle and force, presence and weight. She possesses space. She concedes nothing.

For much of the film’s two-month shoot in 2022, Bening, now 65, spent three to eight hours a day in the water, in a 233-by-233-foot tank off the coast of the Dominican Republic. Two stunt doubles stood idly by. The film’s husband-and-wife directors, Jimmy Chin and Elizabeth Chai Vasarhelyi, are no strangers to feats of athleticism and grit: Their Academy Award-winning documentary, “Free Solo” (2018), chronicles the American rock climber Alex Honnold’s terrifying ascent without ropes or safety gear of the 3,000-foot cliff El Capitan in Yosemite National Park. But watching Bening, they were astounded. “The stunt coordinator said, ‘This is crazy,’” Chin, 50, recalls. “ ‘Nobody does this.’” She did long stints in a constricting full-body jellyfish-proof suit while wearing a silicone mask and acrylic retainers, which Nyad had used to keep jellyfish from slipping into her mouth and stinging her tongue — a setup that made it tough to breathe. All the while Bening had to act, of course: the wild agony of a jellyfish attack, the disorientation as her strength fades.

In theater — Bening’s first love; she did not appear in a film until she was 30 — truth is conjured out of scraps and sometimes less, and actors may take on any age or body type, without makeup or prosthetics, and be believed. But in film, a genre that visually collapses the distance between viewer and performer, more is required. Before “Nyad,” Bening’s most intensive ocean experience had been working as a cook on a scuba diving boat off San Diego when she was 16. So she started training with the American Olympic swimmer Rada Owen in 2021, a year before shooting. Owen “also coaches kids, so she was used to dealing with beginners,” Bening tells me over a late breakfast in Los Angeles in June, under the brooding of the marine layer, calmly elegant in dark jeans and a plaid shirt unbuttoned two stops below the neck.

The first time she plunged into a pool after reading the script, she was almost immediately out of breath. “I had no idea what I was doing,” she says. “But I liked that.”

IN HER 35 years in film, Bening has shown a particular genius for characters who are themselves performers. Some are literally so, like the blithely dissolute movie extra in the 1990 comedy “Postcards From the Edge” (based on Carrie Fisher’s novel of Hollywood misadventure), who pronounces the malapropism “endolphin rush” with dazzling self-assurance, and the imperious actresses of “Being Julia” (2004), “Film Stars Don’t Die in Liverpool” (2017) and “The Seagull” (2018): creatures of the stage who are unable to shake the habit of pretending when off, each with their own fine shadings of narcissism, coquetry and tenderness. Others bring a facade to their daily encounters, deploying charm to get what they want while holding their real selves in reserve, as with the small-time con artist in “The Grifters” (1990) who wears ditziness like a halo, her voice as sunny and juicy as an orange put to the squeezer, and the ravenous-to-succeed real estate agent in “American Beauty” (1999), with her metronomic mantras and immaculately disheveled hair, which with each scene grows more vertical and more like a barely tamed animal, ready to spring.

Her latest role might seem a departure: a woman with no apparent interest in the social niceties of artifice. “It was liberating,” she says, to play someone so free to pursue what she wants. Yet her version of Nyad is also eyeing the crowd, with the marathon swim as her greatest performance, a bid for the history books and an audience for eternity. What fascinated Bening about the character in the script — and she’s careful to note the distinction between the actual Nyad, 74, whom she befriended while making the film and says is “incredibly warm and charming,” and the domineering persona she plays onscreen, whose thorniest traits give the narrative arc and momentum — was in part the swimmer’s fanatical devotion to her mission. (Because of the SAG-AFTRA strike, which started in July, Nyad, a sports commentator, wasn’t available for an interview.) Bening is drawn to obsessives: She talks admiringly of the 2022 documentary “Turn Every Page,” about the maniacally meticulous biographer Robert Caro, and those who in their drive to master their craft exhibit a sometimes excessive desire for control over not only themselves but the world around them.

She tells me how one night in high school, when she was the lead in a play, during intermission the theater teacher picked up a table and slammed it down on the floor because she thought the cast lacked energy. “She wanted to wake us up,” Bening says, still marveling at the memory. “I was in awe.” The actress loved the disproportionality of it, of caring so much. Too much. “For people who are doing serious things like brain surgery, that’s a different matter,” she says, but “in our case, or with any creative act, it’s not rational to care so much.

“That whole thing about caring — I still feel it,” she says. “And when I notice it in myself, because I’m older now, I go, ‘What is that?’ The thing that keeps you up at night. Sometimes I can’t sleep. I want to sleep.”

Although Bening has portrayed a number of historic figures — among them Senator Dianne Feinstein in “The Report” (2019) — she had never done a full-fledged biopic. She’s tended instead to gravitate toward original material, projects that rely on the imaginations of writers and that are increasingly under threat as studios turn to what they call I.P., or intellectual property, pre-existing entertainment that comes with a built-in fan base. One approach to the biopic is the kind of deep, uncanny impersonation that has won accolades for actors like Austin Butler in last year’s “Elvis.” (Nyad, an openly gay athlete, was already a public figure — having set long-distance swimming records in her 20s — before the fame that came with her Cuba-to-Florida swim.) But Bening knew that for the sake of her latest film’s narrative success, she needed to burrow further into the character’s dark corners, “wanting to portray her in a way that’s authentic,” she says, “but at the same time have some laughs and tell a story that people enjoy.”

Bening has long been heralded for playing so-called difficult women, from the monumentally self-absorbed poet manqué in “Running With Scissors” (2006) to the impatiently efficient doctor with a drifty wife in “The Kids Are All Right” (2010), convinced that she alone is keeping her family afloat (she’s not wrong). “It’s not about quote-unquote strong women,” she says. “That’s really boring, to only have stories about strong people. We need to know: What are their faults? Their blind spots? We all have them.”

Sometimes audiences resist, wanting more gold-hearted heroines to root for. “She captures female intelligence, power and strength,” says the director Mike Mills, 57, who entrusted Bening with a role inspired by his mother in the quietly profound and profoundly funny “20th Century Women” (2016). “Which the world isn’t always ready for.” After “Nyad” premiered at the Telluride Film Festival in September, an article in Variety suggested that the title character might be too “challenging” for viewers — in other words, hard to love. In any script, Bening sees herself as her character’s “advocate,” she says. “I felt very protective of Diana. Can you imagine someone playing you — how vulnerable you would feel?” (Bening says that the two of them “ended up being able to talk very frankly,” and when Nyad visited the set, they swam together in the ocean.) Vasarhelyi, 44, recalls deep conversations over a tricky scene in which the swimmer tries to bulldoze her navigator into going back out to sea after he’s told her the weather conditions are too dangerous. Bening experimented with different registers, testing how far she could take the character’s reckless disregard for the lives of others without crossing the line into villainy. But there’s no malice to her Nyad, just a single-minded ambition of the type that tends to be applauded in male leads (see, most recently, Cillian Murphy in “Oppenheimer”).

“How to get it right?” she asks. “It’s always a bit of a gamble. When you’re making something, you just don’t know.”

WHEN BENING was trying to break into films in her late 20s, after seven years as a stage actress in San Francisco, Denver and New York (where she made her Broadway debut in 1987 in Tina Howe’s “Coastal Disturbances” as a young woman oscillating between neurosis and rapture, for which she earned her first Tony nomination), she auditioned for “Dangerous Liaisons” (1988), an adaptation of a play based on Pierre Choderlos de Laclos’s barbed 18th-century novel about the antics of restless aristocrats. Hardly any lines were on offer — she was up for the role of the saucy courtesan on whose alabaster backside the libertine Valmont pens a letter — and she didn’t get the part. But shortly after, in an odd and maybe karmic coincidence, she instead landed one of the leads, the Marquise de Merteuil, in Milos Forman’s “Valmont” (1989), which draws from the same material.

By then, Glenn Close, in the 1988 version, had made the character her own. Rarely do you get to see two world-class actresses go head-to-head in the same role at almost the same time, although at that point Close already had four Oscar nominations under her belt and Bening, 11 years younger, had no Hollywood credits beyond a few minutes on a 1987 episode of “Miami Vice” and a single film, the largely unnoticed 1988 farce “The Great Outdoors.” Where Close as Merteuil is scornfully magisterial, Bening is silkily sly, half-kitten, half-snake. “Dangerous Liaisons” is the greater film: It gives the antics of its louche characters the heft of tragedy, which is a kind of redemption. “Valmont,” which flopped in its rival’s wake, is frothier and thus ultimately bleaker. You can hear the devastation coming in Bening’s laughter when she reveals to Valmont, her ex-lover, that she’s been sleeping with a younger man. Even as she laughs — and keeps laughing, cruelly, triumphantly and then fraying into hysteria — she knows she’s gone too far; that this is a pyrrhic victory, a blow from which they, but above all she, will never recover.

“She’s so deft that way, to be serious and funny at the same time, to flip that switch so fast,” says Lisa Cholodenko, 59, who directed Bening in “The Kids Are All Right.” An entire taxonomy could be organized around Bening’s laughter, which spans octaves, from Champagne bubbles to the peatiest depths of Scotch. Bening can do more with a laugh than most actors do with whole monologues. In “American Beauty,” humiliated at a party by her husband’s flat-affect revelations, she comes close to opera, with a cascade of giggles ascending into little high near yips. Her bit-part floozy in “Postcards From the Edge” has only three minutes of screen time but makes of it an incandescence, opposite Meryl Streep, no less, offering at one point a low, worldly chuckle, then dropping her jaw so the sound kicks up to the roof of her mouth and becomes an almost conspiratorial snicker. There’s a tinge of one-upmanship — she and Streep’s character have bedded the same man — but so faint that, were she accused of such a thing, she could bat her lashes and claim plausible deniability.

This ability to tap into ever-shifting microclimates of mood may have saved Bening early on from being defined (and confined) by her looks. Forman, who cast her in “Valmont,” clearly saw how she could use the appearance of vulnerability as a weapon, with her delicate, fine-boned face blossoming upward like a heart. So did the director Stephen Frears, who passed on her for “Dangerous Liaisons” but a year later gave her what would become her breakout role, as Myra Langtry, the giddily upbeat con artist in “The Grifters.” Here again Bening evades the obvious, rejecting the standard markers of a femme fatale. When a jeweler tells Langtry, not unkindly, that the goods she hopes to sell are fake, she stops at the door on the way out, closes her eyes and smiles, so purely that it’s not even a con, and turns, beaming, to offer the jeweler the “one thing” she has left. “You’re looking right at it,” she says and, instead of bravado or desperation, what comes through in her voice is the bright pop of optimism: the expectation that, no matter how cornered, through sheer willpower she can manifest an escape.

The tabloid headline from Bening’s star turn in “Bugsy” (1991), released when she was 33, was that she’d won the heart of the film’s lead, Warren Beatty, 21 years her senior and, for three decades, Hollywood’s most tenacious bachelor. While the film was still being edited, Bening announced that she was pregnant, and the couple married in 1992; they had their 31st anniversary this year. In the clamor over their love story, it was easy to miss the radical refusal at the heart of her performance as the gun moll Virginia Hill, who doesn’t tease in the way of a classic siren so much as lay down terms, and who insists on treating her gangster lover as an equal.

If there’s a through line in Bening’s work, it’s how her characters seem ever to be negotiating their status as objects of desire — although what they’re really grappling with is power: how to get it, wield it and keep it, in a world threatening to take it away at every step, which closely tracks the shifts in the zeitgeist from decade to decade. She has a knack for appearing in films that define the moment: “The Grifters,” which is based on a 1963 novel and speaks to the amoral avarice of boom-time America in the Reagan years; “American Beauty,” a commentary on the spiritual dead end of American prosperity; “The Kids Are All Right,” with its relaxed, matter-of-fact treatment of gay marriage. When I ask if this is a quality she explicitly looks for in a script, she demurs: “It’s all in the writing,” she says, adding that it’s important to remember that in the midst of the Writers Guild of America strike.

Part of the battle sometimes is simply claiming the leading role, if only in her characters’ own lives. There’s a parallel here to Hollywood itself, which remains resistant to the idea of the older woman as the protagonist. Bening has defied that to a certain extent: “Nyad” is the eighth film in which she’s played a major role in the past decade. Not all found success at the box office. “I’ve made so many movies that nobody paid any attention to,” she says. “In my profession, you do a lot that people aren’t interested in — but we are.” While making “Nyad,” she says, it struck her that “it wouldn’t have mattered” if Nyad had never completed the swim; if she had just tried and tried again, always falling short and always rallying for a return, however stung, swollen, battered and sapped of strength. Until “the efforting,” as Bening puts it, became an achievement itself.

THE ACTRESS has appeared in nearly 40 films throughout her career, and yet in recent years she’s been somewhat out of the public eye, less visible than some of her peers, like Angela Bassett, Frances McDormand, Julianne Moore and Tilda Swinton. This is hardly for a lack of ambition. Rather, she seems, almost anachronistically, not particularly interested in putting herself forward, beyond the screen. Ask Bening about herself and you may discover that you’re suddenly talking about someone else. She’s a master at the gentle deflection and quick to praise the contributions of others, saying that one of the perks of the job is being surrounded by interesting people who are passionate about what they do, from the underwater photographer Pete Zuccarini, who shot pictures on the “Nyad” set (“He takes this gigantic breath and then he goes down”) to her “beast” of a co-star Jodie Foster, who plays Nyad’s best friend and reluctant coach with equal parts generosity and exasperation (“She’s a badass, and she doesn’t suffer fools and she’s smart as hell”).

This attunement to others is in part a reflection of Bening’s time on the stage, where the bond of the ensemble is paramount. “There’s a built-in selfishness to film acting,” says the playwright and actor Tracy Letts, 58, who starred alongside Bening in “All My Sons” on Broadway in 2019. The theater demands a kind of self-effacement in which, he says, “your concern is not making yourself look good but making everybody around you look good.”

Letts wondered if Bening’s gifts — “I’m a bit wistful that we might’ve lost the great American theater actress to films” — could be attributed to her “Midwestern sensibility.” She was born in Topeka, Kan., spent her early childhood in Wichita and still thinks of her family as Midwestern, even though they moved to San Diego when she was 7. A trace of Midwestern propriety clung to her the first time she met with movie agents in New York when she was 25: “I remember seeing another girl who was in jeans and looked really casual and kind of hip, and I was in this little suit, a skirt and blouse,” she recalls. Even now, despite more than half a lifetime in Los Angeles — she and Beatty, 86, are known for presiding over lively dinner parties (“If you go to that household, you’ve got to be prepared to talk about politics and 20th-century history,” Mills says) — something of the Midwest persists in her public manner, that paradox of simultaneous warmth and reserve. For our breakfast, she chooses an unassuming neighborhood spot in the San Fernando Valley where the waiter treats her exactly as he treats me, with no special deference. When I tell Bening that after our meeting I’m visiting my father-in-law, who lives nearby, she offers to give me a ride.

You could argue that the ensemble is in fact Bening’s natural habitat. She was the last of four children born within five years, and she and Beatty have four children of their own. (Only the youngest, Ella Beatty, 23, is an actress, too, and graduated from Juilliard last year.) When Bening had their first child, she was startled to find that she’d lost her desire to act, though she’s uneasy with the idealization of motherhood, “what a good mother is or isn’t — what a good woman is or isn’t — and is that defined by sacrificing the self?” Nevertheless, there were roles she turned down — famously, Catwoman in “Batman Returns” (1992) — because she was pregnant or didn’t want to be away from her children for too long. “The thing that being in the theater really teaches you is that sense of mutual vulnerability and mutual purpose,” she says, which could as easily be a description of a family. “She’s really close to her parents,” Vasarhelyi says. Bening’s mother, now 94, was a stay-at-home mom who sang in church; her father, who died in September at the age of 97, sold insurance. Up until his death, they still lived in the same ranch-style house in the neighborhood that Bening grew up in, San Carlos.

While in high school, Bening did some secretarial work for her father, who was teaching classes on Dale Carnegie’s principles of salesmanship. Foremost among them: being interested in other people. The key is not faking it. You have to genuinely care.

BENING’S physical transformation as Nyad is remarkable, rigorous and free of vanity. But equally so, perhaps, is the transformation she’s undergone onscreen and off over the past two decades: her acceptance of the steady, mundane process of aging, which so many in Hollywood, female and male, have tried to defy. In casting the role, Vasarhelyi says, “We needed an actor who wasn’t afraid of what a 64-year-old looks like.”

Not that Bening thinks her decision to forgo cosmetic alterations is in any way noble. “There’s all this pressure on women to have plastic surgery,” she says. “And then when they do, they’re punished for it.” She hardly set out to be a flag-bearer for aging gracefully, whatever that means. “You do it as you go,” Bening says. “As I’ve been inching along, I’ve felt more and more free.” She remembers, from her childhood, her mother slathering on Noxzema or Ponds. That was it. When her mother went out, she “had her eyebrows done and her lipstick on,” Bening says. “Now I’m just down to the lipstick.” As if on cue, she pulls a lipstick out of her bag and slides on the color without breaking eye contact, no mirror required. It’s a reminder of how much of beauty is aura and certainty — knowing who you are, that you have a place in the world.

“Am I thrilled every time I see my wrinkles? No,” she says. “But when I thought about being an actress, I always imagined it happening over my whole lifetime. That was my aspiration.” The trouble — and this is a banality — is that Hollywood doesn’t seem to know what to do with older actresses who aren’t straining to look younger. In the 1990s, Bening was consistently paired onscreen with older men: Michael Douglas (a 14-year gap), Robert De Niro (15), Harrison Ford (16) and Beatty (21). Then the pendulum swung and, in “Being Julia,” she was 22 years older than her callow (and frankly boring) lover, played by Shaun Evans, and 18 years older than Corey Stoll in “The Seagull” (2018). She reunited with her husband onscreen for “Rules Don’t Apply” in 2016, only she, at 58, was relegated to the role of mother of the young starlet, whom he — at age 79, playing Howard Hughes — seduces.

In an early scene in “Nyad,” Bening, restless and keyed up, slashes at a Ping-Pong ball. “I’m not done,” she says. “I have more in me.” Now, in this improvised restaurant backyard abutting a parking lot, with AstroTurf below and the June gloom over the valley starting to clear, Bening is unruffled. She acknowledges that she’s privileged to be able to choose whether to work or not; to take only the jobs she wants. “But there’s always something I want,” she says, her voice sinking almost to her ribs. She doesn’t move, but it’s as if she’s leaned in. There’s a flicker in her eyes — wickedness? exultation? — and it’s gone.

HENRY TAYLOR, who at 65 is one of the 21st century’s most celebrated painters, works out of an unassuming space in Los Angeles, close enough to Koreatown that a nearby restaurant specializes in chueo-tang, or mudfish stew. His studio’s not much more than a large room, next door to an exterminator and what seems to be an active warehouse, from where the sounds of industrial equipment could be heard. There were Oriental and Moroccan rugs on the concrete floor and paintings, three deep, leaning against the walls.

Taylor was sitting at a wooden coffee table, which was covered in sunflower seeds and art books. He wore a Thom Browne cardigan, a mostly unbuttoned dress shirt and jeans that kept falling off his hips. His hairline has crept to the top of his head, but he looks younger than his years, especially when he smiles, though it would take him a minute to be in a smiling mood. It was 11 a.m., and he is not a morning person. He smoked a cigarette with a sense of urgency.

“I think I’m just getting older,” was the first thing Taylor said after we exchanged pleasantries. “I’ve been doing this for so long. I could come in here and work one day and go hard. And the next day I can’t do [expletive]. It wasn’t like that 20 years ago. You forget where you are when you’re painting. You don’t even realize it, but you get worn out.”

One of Taylor’s most famous paintings is 2017’s “The Times Thay Aint a Changing, Fast Enough!,” an elegy to Philando Castile, a nutrition services supervisor at a Montessori magnet school in St. Paul, Minn., who was killed at the age of 32 by a police officer during a traffic stop in 2016. In the painting, Castile’s one visible eye bulges open in a kind of shock, as though he is astonished and appalled to be eternally trapped in this moment. The cop’s gun appears almost peripherally, through a window of Castile’s car. Not pictured, but still present, as it’s her perspective we’re seeing, is Castile’s girlfriend, Diamond Reynolds, who livestreamed a video of the encounter on Facebook from the passenger seat.

When Taylor was younger, back before it occurred to him that he could make a living from painting, he thought he might become a writer instead, and he has a writer’s impulse for storytelling. He mentions Mark Dever, his journalism professor at the community college in Oxnard, the California city where he was raised, an hour and a half drive up the coast from Los Angeles. Taylor studied with him for only a year before Dever died in a car accident. But his advice has always stuck with Taylor. “Get the story,” Dever would say. “Go back and get the truth.”

The responsibility that Taylor feels toward the truth makes “figurative painter,” which is what Taylor undeniably is, also an insufficient categorization. He begins with simple brushstrokes and a loose hand. His colors are bright and vibrant, but not obsessed or labored over; he usually paints things the color that they are. Many of his works would look, in another artist’s hands, unfinished — faces not filled in, body parts missing. A good deal of his portrait of Castile is just the outside world in the background, an expanse of yellow color, going about its business indifferently; the missing details are deliberate — they don’t detract from but rather add to the subject’s identity. Sometimes, Taylor will paint so quickly, he’ll feel guilty he didn’t work on a canvas longer. But it requires an enormous amount of skill and restraint to paint in a way that looks so effortless and free.

Take his 2013 painting of Steve Cannon, a writer who founded the organization A Gathering of the Tribes and converted his New York apartment into a gallery. It was on view at the Museum of Contemporary Art in Los Angeles in “B Side,” a survey of Taylor’s work that opened in 2022 and recently traveled to the Whitney Museum of American Art in New York. Cannon is seated with his legs crossed, but his feet are missing. His legs melt into the green portion of the background of the canvas. And he’s not actually sitting but floating, as if suspended in midair. He’s biting the pinkie nail of one hand, while the other disappears into his torso, like Taylor began to work on the limb and then, deeming it unnecessary to the story, edited out the detail. It’s the face he was focusing on, and it’s there that Cannon, who was blind — his eyes are obscured by sunglasses — appears to stare out from the painting as if the viewer were caught in his gaze, and not the other way around. “I always felt like the canvas had a memory,” Taylor told me about how he paints. And in that regard, what he does isn’t so different from the work of a journalist — discovering a person’s memories and reporting back what he saw.

THE PAINTINGS of Henry Taylor could be categorized into two major strands — the first made up of works from life. If a person spends enough time with Taylor, chances are good he’ll paint them. He’s restless and almost comically prolific. Though he tries not to, sometimes he can’t help but draw while he drives, eyes on the road, a pad balanced on his knees. During the Covid-19 shutdown, he painted his neighbors. At his last big museum show, in 2012, at MoMA PS1 in Queens, much of the museum’s staff ended up on the wall. He’s painted celebrities, addicts, journalists, other artists, girlfriends, panhandlers — really, anyone who happens to be around. But he doesn’t take people sitting for him lightly. Over the years, he’s painted many pictures of his mother, Cora, for instance. In one, she isn’t even depicted. Taylor instead paints a pan of cornbread on a stove, the words “corn bread” floating in a turquoise background the color of an old Cadillac, and the letters “C-O-R-A” circled. But Cora only sat for her son once. That painting was stolen, which still upsets Taylor. (The title of a comprehensive 2018 monograph is “The Only Portrait I Ever Painted of My Momma Was Stolen.”)

The other strand of Taylor’s art concerns a larger, shared American history. Subjects don’t sit for these works, but most of them are still portraits, albeit ones that reflect a collective memory. He’s painted Barack and Michelle Obama, Bob Dylan, Alice Coachman (the track-and-field star who was the first Black woman to win a gold medal at the Olympics), Chuck Berry, Jay-Z (for a cover of this magazine), Stanley Williams (a co-founder of the Crips) and Haile Selassie I, the Ethiopian emperor, in full military regalia, standing in front of a golden throne. Even as he engages directly with a didactic, epic tradition of history painting dating back to the 17th century, there’s also something unmonumental about Taylor’s overall project. It’s all so personal, whether he’s related by blood to the person he’s painting or not. He frequently adopts a kind of omniscience in his perspective, as he does with the piece portraying Castile, which is a painting not just of its subject’s final moments but of the public’s consumption of them. And that is also what the work is about — how this extreme type of American violence recurs until it becomes digested as so much spectacle.

IN CONVERSATION, he’ll bring up the painters who’ve influenced him — Pablo Picasso, Philip Guston, Henri Matisse, Robert Rauschenberg — with a certain embarrassment, hesitant to sound as if he thinks of himself as some canonical figure, even though he now is. His portrait of Castile, in particular, became a flashpoint in the early years of Donald Trump’s presidency; during his 2016 campaign, he’d remarked of Reynolds’s video of Castile’s death that it was “tough to watch … but we are going to treat our police with respect.” The painting was exhibited at the Whitney Biennial in 2017, not long before the officer who killed Castile was acquitted by a majority-white jury of all charges.

Taylor’s inclusion in the Biennial turned him into a spokesperson for Black America and changed the stakes of what (and who) the art industry believes to have value. Few other painters, not even Picasso, have been held up as a totem of the culture they inhabit as explicitly as Taylor has. His work “helped fuel an explosion of interest in Black figuration,” as a New York Times article put it last year, going on to list Jordan Casteel, Kerry James Marshall, Jennifer Packer and Amy Sherald as some of Taylor’s peers who have likewise experienced critical and institutional success at least in part for their depictions of Black lives. “The market is also paying close attention,” that article noted. Barack Obama asked Taylor for a painting to give to Michelle on her birthday. This year, Pharrell Williams used his paintings in designs for his debut collection as the men’s creative director at Louis Vuitton. Taylor’s paintings formed the backdrop of Kendrick Lamar’s 2023 North American tour. He’d spent years working successfully, but quietly. And suddenly he was the voice of a generation.

Another painting that debuted in the Whitney Biennial in 2017 was a portrait of Emmett Till, who, while on a trip in August 1955 from Chicago to Mississippi to visit relatives, was abducted at gunpoint by two white men who believed Till had flirted with one of their wives. They tortured him, killed him and then discarded his body in the Tallahatchie River. The men were found not guilty of kidnapping and murder by an all-white, all-male jury. Till’s mother transported her son back to Chicago and held a funeral with an open coffin, which was attended by tens of thousands, including members of the press, who published images of the horrific violence inflicted upon the 14-year-old. Some 60 years later, a white woman, Dana Schutz, painted Till in his coffin. Protesters lined up in front of the work. The artist and writer Hannah Black wrote an open letter to the museum not just asking for the removal of that painting from the show but recommending that it be destroyed. “[I]t is not acceptable for a white person to transmute Black suffering into profit and fun, though the practice has been normalized for a long time,” she wrote.

Taylor understood the anger at Schutz, but he didn’t share it. He’s compared the situation to being angry at the novelist William Styron for writing about the slave rebellion of Nat Turner, or at Bob Dylan for singing about racial violence and the activist George Jackson. When Taylor was growing up, his older brother Randy, who had been associated with the Black Panthers, had given him Jackson’s 1972 book, “Blood in My Eye,” a manifesto calling for guerrilla warfare to overthrow the U.S. government. Jackson wrote it while serving an indefinite sentence at California’s San Quentin State Prison for stealing $70 from a gas station; he was killed during an attempted escape. “George Jackson” was the first song Taylor, then in ninth grade, had ever heard by Dylan. Now Taylor quotes his lyrics from memory. It wasn’t a coincidence that he’d invoked the 1963 record “The Times They Are a-Changin’” in the title for his painting of Castile. He’d painted Castile the same way Dylan sings about Medgar Evers on that album, in the song “Only a Pawn in Their Game,” taking the widest possible view of the tragedy, implicating everyone. Evers was a leader of the Mississippi N.A.A.C.P. who was murdered in his driveway in 1962 by a white supremacist. Dylan sings about how the bullet wasn’t just fired by “the poor white man” — the fertilizer salesman and white knight of the Ku Klux Klan who’d pulled the trigger. It was also fired by his teachers, who’d told the killer his whole life “to keep up his hate.” It was fired by the rich politicians telling all those poor white men, “You’re better than them, you been born with white skin.”

Taylor was ambivalent about becoming a messenger for Black culture, whose works were status symbols for a wealthy elite. He knew he was an artist, no further adjective necessary. Success offered him more freedom and security than he’d ever had in his life — he certainly didn’t have to convince anyone to sit for him anymore. Yet he felt a pressure to live up to these new expectations, and a fear that they would make his work less authentic. He felt fortunate, but then he’d always felt fortunate, even back when no one knew he was a painter because he was too embarrassed to say that out loud. At least, he told me, “I had something I was passionate about.” Now, though, there were things to delegate and a business to manage. He didn’t want to be a spokesperson. He wanted to be in the studio, painting or thinking about painting. “Sometimes I just want to [expletive] leave, bro,” he said. “Running errands, phone calls — it gets to be too much. I got 300 voice mails. I don’t have time for that, man. And when you get old, you just want to make more.” He wanted to remember as much as he could while he was still able to.

GROWING UP in Oxnard, Taylor was the youngest of eight children. Because of that, he learned how to observe; he’d later find this skill useful when making people comfortable enough to let him paint them. His mother cleaned houses. His father, Hershal, was an industrial painter who had a contract with the local navy base; on the weekends, he’d paint houses. When Taylor didn’t have school, he’d sometimes go to work with his father, watching him paint with big rollers and brushes.

The Taylor family came from a town called Naples in East Texas. Taylor’s grandfather, Ardmore, wouldn’t pick cotton, so he broke horses and gambled on the side. When Taylor’s father was 9, Ardmore was ambushed and shot by unknown assailants. Ardmore returned home to have his wife dress and clean the wound with kerosene; then he got on a horse to look for the people who had tried to kill him. They ambushed him again and shot him to death. Taylor’s father and grandmother had to collect the body.

This story, and Ardmore himself, haunts Taylor’s paintings. He returns to the image of a dark horse again and again. It appears the way a loved one often shows up in a dream — suddenly, ambiguously, sometimes invisibly. The phrase “dark horse,” meaning someone who’s been underestimated, derives from racing slang. The dark horse is also an enduring symbol in the history of painting, from Picasso to Bill Traylor, a sharecropper and farmhand born into slavery in Alabama who taught himself to paint at age 85 and for whom horses represented both freedom and exploitation. In the 19th century, plantations ran on the backs of horses, which were often trained by enslaved people. It’s hard not to read Taylor’s dark horse as the spirit of Ardmore, but the figure can also be seen as Taylor himself, silently standing watch in the background as he had in childhood.

Taylor enrolled in community college at 19 but stayed longer than a lot of the other students, attending classes on and off for almost six years. He took several courses taught by James Jarvaise, an abstract painter who ran the school’s art program. Jarvaise was included in a 1959-60 show at New York’s Museum of Modern Art, “Sixteen Americans,” alongside Rauschenberg, Jasper Johns, Louise Nevelson and Frank Stella, though he never became a household name. He’d offer insightful encouragement like “Sometimes a straight line has to be crooked.” Mostly Jarvaise simply painted every day, with a discipline that impressed itself on Taylor. When younger artists come to Taylor now asking for advice, he tells them what Jarvaise told him: Just keep painting.

Jarvaise also suggested that Taylor apply to California Institute of Arts, which, by the time he arrived in 1990, was in the wake of one of its “painting is dead” phases. Taylor and one other student, Mark Bradford — who shows at the same gallery as Taylor, Hauser & Wirth — were among the few painters there. The teachers made him read Michel Foucault and Jacques Derrida, which he hated. “I just felt like an idiot,” he said. And Taylor, then in his early 30s and already a father, was older than the other students. (He has two grown children, a son and daughter, as well as another daughter born in 2021, all of whom have appeared in his paintings.) He paid for CalArts by working as a nurse at Camarillo State Mental Hospital, which he had begun doing in 1984. His official title was psychiatric technician. He can still remember the first time he saw shock treatment performed on a patient. “It was like a little car battery,” he said. “There wasn’t nothing sophisticated at all.”

He discovered that the same things that made him a good nurse — his willingness to talk to anyone and to listen to them — also made him a good artist. He’d sketch the patients, with their permission. Most of his Camarillo works are just pencil drawings on paper, many of them little more than a suggestion of the subject, but they’re also his first serious works, the moment Taylor emerged in full not just as a formal master but as an unusually empathetic presence. He captured the grimness of the patients’ lives while granting them a dignity one doesn’t usually associate with a psych ward.

At CalArts, whenever he had a crit — brutal experiences where the students judged one another’s work out loud — he’d first drive to Santa Barbara, where Jarvaise lived. “I’m going to CalArts because I trusted him,” Taylor said. “And I would say, ‘Hey, man, you gonna tell me to go to this school, then I need your help.’ And he’d give me confidence.”

TAYLOR’S relationship with his father wasn’t easy. “He had this hard side to him,” Taylor said. “He would fight you in a minute.” He never seemed to get over the death of his own father. Hershal Taylor had six sons, and he referred to them as his bullets. “Meet my bullets,” he’d tell people.

Father and son never talked about painting. But at his CalArts graduation show in 1995, he painted quotes from Hershal all over the gallery walls. Yet he hadn’t told his father, who was living in Oakland at the time, about the show. He died shortly after the opening. Taylor had to identify his father at the morgue. “He looked just like me,” he said. More than anything, it was the legs. He’d never thought about his father’s legs before, but now they stuck in Taylor’s mind: The two men had the same build. Later on, he made some sketches of the memory and recently has been painting it. When Taylor got home and checked his voice mail, he was surprised to find a message from his father. He knew about the exhibition anyway. “And he asked me,” Taylor recalled, “ ‘Hey, how was your show?’”

It took nearly 15 years after his CalArts graduation for Taylor, then in his 40s and still painting every day, to receive any attention from a commercial gallery. He lived in Thousand Oaks — right next to “where the Rodney King trial was held” is how he described it — and sometimes he’d drive to Los Angeles and visit the galleries, bringing paintings he’d made on cigarette boxes. But he couldn’t get anyone interested until 2004, when Kathryn Brennan, who owned a gallery called Sister, offered him his first exhibition. That gave him the motivation he needed to move to Los Angeles.

He had his first museum show in 2007 at the Studio Museum in Harlem, which demonstrated his range from the personal (paintings of cousins, brothers, his parents) to the topical (a portrait of Sean Bell, a 23-year-old Queens man who was shot to death by police on the morning of his wedding in 2006; the three officers indicted, who’d fired an estimated 50 rounds at the unarmed Bell, were acquitted of all charges). But critics wouldn’t write about him. Besides the Studio Museum, there were just a handful of New York galleries that regularly showed works by living Black artists that depicted Black people. As long as those works didn’t make any money, the art business was uninterested. If Taylor received any attention at all, he was branded an outsider or folk artist, labels he found demeaning.

But he also had dedicated supporters, among them Klaus Biesenbach, who was the director of MoMA PS1 during his show there in 2012, after which the art world began taking Taylor seriously. A review in The Times compares him to an “outsider,” but adds, “He paints roughly the rough world of his own experience, but he does so with a rare spirit of generosity and love.” I interviewed Taylor around this time for a publication that no longer exists. He really hasn’t changed much in the 11-year interim. His clothes are conspicuously nicer, but that’s about it. That interview took place at a dreary sublet apartment in Long Island City that recalled his current studio. He kept egg cartons full of acrylic paint in a stack on his small kitchen counter and, when he felt like painting, he would plop a carton onto the stove and sit in the kitchen, while a visitor sat in the living room, which got a bit of natural light. During the interview, he’d ask me questions like, “If someone gave you the money to do whatever you wanted for a year, what would you do?” While we were talking, he painted my portrait.

SOMETIMES Taylor has to sit with the paintings for a while before he feels done with them. After we spent a few hours together in his Los Angeles studio, he put on the second half of Dylan’s 2006 album, “Modern Times,” and showed me some of the paintings for which he didn’t have plans yet. A lot of them were stuffed into a big wooden rack. Most were portraits. “These are some ladies I met in Spain,” he said.

On the wall adjacent to the rack was a large painting of James Brown and the Famous Flames at the height of their powers, circa 1964, judging from the outfits. Taylor depicted the band in a moment of exhausted, focused attention, as Brown, in almost ecclesiastical purple, shuffles casually in front of them. Across the top is the phrase “King James.” I stared at the canvas throughout the day, and not only because it was the painting nearest to me. I thought it was a masterpiece. But there was also something uncharacteristically finished about it, as though the longer it sat in the studio, the more spontaneity it lost. Even the lettering looked overworked, slightly off. It was Henry Taylor doing Henry Taylor, like a pop star in his Vegas residency phase. But this is also what made it a great painting. As with Castile, he wasn’t looking merely at Brown but past him, at the audience’s perspective, and in doing so, he’d both problematized and humanized his subject, which was not so much Brown and his band as it was the spectator’s gaze, the weight of expectations. When I blurted out, “It’s remarkable,” he regarded the painting with indifference. “I kinda like it,” he said. “I don’t know about the lettering.”

I asked him if he ever thought, after finishing a painting, “I really want people to see this.” The question felt rather mundane to me, but it was the only time I saw Taylor taken aback. Finally, he said, “That’s a good question, bro. That might be the best question I’ve ever had.” But he didn’t answer it, not directly. He paced around the studio a little, then grabbed a cup of black acrylic and dipped a brush into it. He stood before one of the canvases leaning against a wall.

This one depicted five young men in shirt sleeves and black ties, posing on a basketball court — an image he has painted many times. That was Randy on one side, and their cousin Johnny Walker, who had been a high jumper in high school. Crouched down, legs bent, was Clint Strozier, who was good enough at football to play for the University of Southern California. On the far right was another cousin, named George Washington, who spoke fluent Spanish. They were all four years older than Taylor, but they treated him as an equal. His brother was a straight-A student who went to medical school. He met the labor leader Cesar Chavez and told his younger brother about how Chavez named his two dogs Huelga (Spanish for “strike”) and Boycott. “I’d put him in a room against anybody,” Taylor said of Randy. “He belongs alongside Stokely Carmichael. He had more balls than I ever had.”

But of all of them, only Henry Taylor had managed to fulfill his potential, which didn’t seem fair to him. Everyone else had some there-but-for-the-grace-of-God story, like Randy. After someone close to him died in a car accident, he dropped out of school, moved to rural Texas and began living off the grid. It was so random, the way some people made it and others didn’t. “It makes you see how precarious life is,” Taylor told me. “How it can just change.” That was why he made the painting, and why he kept returning to it.

He took his brush and, in the blue sky of the background, made a big black triangle and began to fill it in with paint. “I’m just marking this,” he said, “so I don’t forget about it later.”