Annette Bening Knows a Thing or Two About Difficult Women

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.”

DANA OWENS was just 15 when she and her friends started “going over,” as they called it, from Newark, N.J., to the Latin Quarter, a nightclub in Midtown Manhattan. She’d finish her shift at Burger King, change into her Swatch tracksuit and take the commuter train under the Hudson River and the subway up to Times Square, where a bouncer would pat her down for weapons. Once inside, she recalls, “it’s tight and it’s hectic and the energy is crazy.” Up on the stage were M.C.s like Melle Mel and Big Daddy Kane — artists she’d dreamed about seeing live — whose faces she knew from posters or album covers (rap videos were still rare in 1985). There, where culture was being made in real time, D.J.s tested out records on the crowd before playing them on the radio, and Owens picked up moves that nobody at Irvington High School knew until she brought them back across the river.

The sensitive, magnetic kid who would come to be known as Queen Latifah was a quick study. As a teenager, she wrote poetry inspired by the Black Arts Movement writer Nikki Giovanni, read science fiction novels by Octavia E. Butler and played basketball on a team that won two state championships. She grew up with house music, show tunes, reggae, jazz and gospel. But the Latin Quarter (or Quarters, as it was commonly referred to) was the crucible of a whole new sound, a place where M.C.s delivered praise songs, usually about their own prowess, scored by ingenious soul samples and abrasive effects. There were sets by hot female acts like Salt-N-Pepa (whose 1986 track “My Mic Sounds Nice” was, Latifah says, “a banger”) and D.J. Jazzy Joyce (who wore sweatpants and sneakers like she did). Among the most galvanizing was MC Lyte, a virtuoso performer from Brooklyn even younger than her. Latifah remembers thinking, “If Lyte can do it. …” Hip-hop was driven by confident, competitive young people who watched one another excel and thought, “Why not me?” They thrived on rap and dance battles and actual fights. “But in the midst of all this chaos,” Latifah says, “was the hottest music you ever saw in your life.” She smiles, adding, “But I was not supposed to be in this club.”

Such illicit crossings have defined Latifah’s professional life, as has her refusal to land on any one thing — a quality that, I discover on an afternoon this past July, also characterizes her storytelling. We’re sitting in a dimly lit room at the Hit Factory, New York City, a recording studio in NoHo about 40 blocks south of where the Latin Quarter used to be (after closing in 1989, it was replaced by a Ramada Renaissance), and she wants me to picture the scene in its complexity: intensely creative and rightly forbidden. The same 360-degree view is required to understand Latifah herself. She’s often celebrated for her pioneering achievements in hip-hop: She’s the first solo female rapper to have a gold album; later this year, she will become the first woman rapper to receive a Kennedy Center Honor. (She’s also the first hip-hop artist to land a star on the Hollywood Walk of Fame.) But in addition to her four rap albums, Latifah, now 53, has released two jazz albums; hosted two daytime talk shows; and appeared in more than 60 films, many of which she developed with her management and production company, Flavor Unit Entertainment, founded in 1995 with her business partner, Shakim Compere. By 2003, she was as famous for her high-cheek-boned face in cinematic close-up as for her voice, becoming one of CoverGirl’s first full-figured Black models, and later creating her own cosmetics line with the brand geared toward women of color. As the star of the spy thriller “The Equalizer,” now approaching its fourth season on CBS, she became one of the first Black female leads on an hourlong network drama.

A 5-foot-10 Black woman from New Jersey only launches and sustains a career like hers with an implacable sense of self-belief. But her power moves — and her confidence — have also been fostered by tight groups of collaborators. We might call them her “posses,” a concept of rap kinship she advanced on her 1989 single “Princess of the Posse,” then translated into several projects that now represent various phases of her cultural influence. Older hip-hop heads still champion Black feminist anthems such as “Ladies First” (1989), which she recorded with the British rapper Monie Love, and her Grammy-winning track “U.N.I.T.Y.” (1993) with its sonic left hook: “Who you callin’ a bitch?” Slightly younger fans met her on “Living Single,” a sitcom featuring four Black girlfriends in Brooklyn that aired from 1993 to 1998. Her turn as a lesbian bank robber in F. Gary Gray’s outlaw girl-group film “Set It Off” (1996) is now a classic of the genre; and the 2017 comedy in which she co-starred, “Girls Trip,” became the first movie with a Black woman screenwriter (Tracy Oliver, co-writing with Kenya Barris) to gross over $100 million at the box office.

These days, Latifah’s wholesome, general-audience appeal can conceal the force of her impact. But she strategically facilitated several mergers that once seemed highly unlikely and now define our era: between rap and Hollywood, hip-hop and high fashion, Black capitalism and activism. We now take for granted that Ice Cube and Common produce and star in films and TV shows, and that several of rap’s most innovative artists are women (Megan Thee Stallion, Latto). We increasingly see Black actresses onscreen (Viola Davis, Zendaya) representing queer love and desire, and find cover-girl aesthetics embodied by curvy Black artists and models in Rihanna’s Savage X Fenty fashion line. We see this because we are living in a world that Latifah helped make. If she seems like us, it’s largely because she has made us like her — members of a posse she might want to roll with.

LATIFAH, WHO introduced herself simply as La, is wearing her hair in five cornrow braids, and her skin is as radiant as advertised. She compliments my beat-up kitten heels and short haircut. She can’t remember which tracks from her second album, “Nature of a Sista’” (1991), she recorded at the Hit Factory when it was on 54th Street and Broadway. But she does remember being there because it was expensive, she says, and because of “the weight and the breadth” of the history associated with the studio. (Michael Jackson was one of many stars who’ve recorded at its various locations.)

Latifah met Shakim Compere at Irvington High through her mother, Rita Owens, an art teacher. When Latifah signed to Tommy Boy Records in 1989, at age 19, she and Compere — skeptical that any management company would properly represent her — started Flavor Unit Entertainment in a windowless office in Newark. Rita co-owned the company but seldom went to the office (it was filled with cigarette smoke, a habit Compere and Latifah have since quit); her scions had already absorbed her goal-oriented, get-yours-and-give-back approach, itself rooted in the politics of Black self-determination. (Latifah has said that in the 1970s, Rita hosted gatherings whose attendees included the poets Amina and Amiri Baraka, which her daughter later learned were Black Panther meetings.)

Flavor Unit was named for a larger crew of rappers and D.J.s who aimed to put New Jersey on the hip-hop map. It was through practicing with the group that Latifah developed her signature sound: a stately, unhurried flow, hooks she sang herself and a range of diasporic musical references. “Princess of the Posse” was as notable for its use of reggae as for its marriage of rap and song, both of which prefigured the work of Lauryn Hill, another rapper-vocalist from the same area of New Jersey. Latifah wasn’t the first person to do that, or to foreground female empowerment (MC Lyte’s “I Am Woman” came out in 1988), but she synthesized these innovations with a historical consciousness that made her songs at once danceable and righteous. She commanded a range of subjects, from partying (1989’s “Dance for Me”) to politics (that year’s “Evil That Men Do”) to sex (1991’s “How Do I Love Thee”), and her look affirmed her authority. Dressed up but toned down, she wore African prints and soft kufi crowns that skirted both the femme sex appeal of artists like the Real Roxanne and the casual vibe of Roxanne Shanté.

Then there was her name, the sheer audacity of which can be hard to appreciate now that it’s a global brand. “To be a Black girl from Jersey who decides that Dana Owens is no longer big or accurate enough to describe who she is,” says the journalist Danyel Smith, “and to change her name to Queen Latifah — it was just bold.” At the time, Black kids across the country were adopting Arabic names (in the style of their nationalist elders), and Owens felt like “Latifah” captured her inner softness and delicacy, which most people missed. When she added the “Queen” upon signing to Tommy Boy, she was paying homage to South African anti-apartheid struggles while also crowning herself. Jada Pinkett Smith, 52, a close friend and her “Set It Off” co-star, recalls seeing a photo of Latifah at a Baltimore club in the late 1980s. “That was the first time I’d heard a young woman put ‘queen’ before her name,” Pinkett Smith says. It made her think, “We are queens, aren’t we?”

As the only female act in the core group of performers on Public Enemy’s Fear of a Black Planet tour in the early 1990s, Latifah learned how to make the most of the small stage area in front of the headliner’s setup and wore her kufis in part to avoid getting her hair done. (“This is a queen vibe and it’s a soul vibe, but it’s also a saving-me-several-hundred-dollars-a-day vibe,” she says.) Danyel Smith compares Latifah’s persona back then to that of the “neighborhood superstar: the prettiest, coolest girl on the block; the toughest girl, who was still nice to you even though she was popular.” But Latifah’s confidence, while it might have seemed innate, took constant practice. In her 1999 book, “Ladies First: Revelations of a Strong Woman,” she describes being gripped by fear before taking the stage at her first high school talent show: “What if they don’t like me? What if somebody boos?” Then she flipped the question: “What if they love me? What if they give me a standing ovation?” She sang Luther Vandross’s “If Only for One Night,” and the crowd adored it. With every such venture, her confidence expanded, as her older brother, Lancelot Owens Jr., known by his nickname, Winki, told her it would.

She took what she learned from male crews to create spaces for women, defying both the inherent competition among female rappers and their enforced separation: As MC Lyte tells it in the AMC documentary “Hip-Hop: The Songs That Shook America,” her label refused to let her join Latifah and Monie Love on “Ladies First.” That duet became, according to the writer Kierna Mayo, “the first song to openly address sexism in hip-hop,” adding to rap’s race consciousness what we would now call an intersectional analysis. But it began, Love says, with two friends in separate corners of Power Play Studios in Queens, unable to write more than a few lines before rushing back over to share them: “ ‘Listen to this, La!’ ‘Oh, that’s crazy!’” Looking back on their musical interplay, Love describes Latifah’s flow as “majestic” and herself as the queen’s amped-up attendant: She declares herself, in one verse, to be “merrily, merrily, merrily, merrily hyperhappy overjoyed / pleased with all the beats and rhymes my sisters have employed.” The video stitches together a sisterhood of historical figures (Harriet Tubman, Angela Davis and Winnie Mandela are shown in photographs), and several other contemporary female rappers.

Its central image, of Latifah as a military commander knocking white chess pieces off a map, also evokes the makeshift war rooms vital to hip-hop’s early years. At a time when some in the mainstream media framed rap as an artless fad or a scourge (the efforts of an organization called the Parents Music Resource Center, co-founded by Tipper Gore, the wife of future Vice President Al Gore, led to stickers flagging the “explicit lyrics” of rap albums), she and her friends would meet in the studio to debrief about the latest anti-rap slander. “Whatever they said [on the news] is garbage. This is going to last, this is going to influence the world,” Love recalls their saying. “When anybody was feeling like, ‘Man, it’s not gonna happen’ — nope, she’d jump right in.” But even with Latifah’s early successes, there was a precariousness to those years. Compere had to demand money from club promoters reluctant to pay what they’d promised, and she was called upon to navigate thorny questions about censorship from the press. Then, in 1992, Winki was killed in a motorcycle accident at age 24, a loss that nearly undid her. She had bought him the bike — riding was a shared love of theirs — and she couldn’t fathom the life she was building without him. She writes in “Ladies First” that it was only her belief in God that kept her from suicide. Instead, she plunged into drinking and smoking weed, then into work. She made a furious, brilliant album, “Black Reign” (1993), that was dedicated to her brother and is still her favorite.

SHE MOVED into television and film to expand her influence and diversify her options before she aged out of rap. But in one of her first TV roles, in 1991, as Will Smith’s friend turned crush on “The Fresh Prince of Bel-Air” (1990-96), practically every scene included a joke about her weight. By the time she joined the cast of “Living Single,” the jokes were hers. When her character, an ambitious magazine editor named Khadijah, is asked to picture a world without men, she grins: “A bunch of fat, happy women and no crime!” Just as “Living Single” capitalized on the rise of Black sitcoms like “The Cosby Show” and “A Different World” to tell a story that centered Black women, the scholar Amanda Wicks has written, “Set It Off” issued a feminist response to dramas like John Singleton’s “Boyz N the Hood” (1991). Here, too, Latifah seemed freer to shine amid a strong ensemble cast. As Cleo, a bank robber avenging her friends’ traumatic mistreatment by the police, she cranks up her comic timing and reveals new subtleties. In one scene, her character pulls up in a getaway car beside that of her friends. When she realizes one of the women has died of gunshot wounds, her face crumples and she leans toward the steering wheel, as if she doesn’t want even the camera to see her cry.

With “Set It Off,” Latifah joined another group, what the journalist Clover Hope calls in her book, “The Motherlode: 100+ Women Who Made Hip-Hop” (2021), “the first generation of rappers … to build a bankable Hollywood résumé.” Narrating her coterie’s moves, Latifah says, “Will [Smith] did it,” then she did it, “and I’m sure LL [Cool J] was like, ‘Well, if they can do it. …’”

The highlights reel of her acting career — including her Oscar nomination for “Chicago” (2002) — can obscure the fact that she appeared in over 20 films before she was cast as a solo lead, in “Last Holiday” (2006); and several more before she took center stage in a love story of her own, opposite Common in “Just Wright” (2010). She and Compere conceived that one themselves. If forgetting where you came from is the successful hip-hop artist’s cardinal sin, Latifah seems to have averted it by developing thoughtful mainstream films and hiring massive and diverse crews to make them. Most people in Hollywood “call who’s on that same old sheet for them to hire, and it’s comfortable for them,” she says. “But it’s not comfortable for me.” Flipping the script on arguments that colorblind hiring practices seek “the best” candidates, she asks, “How are we gonna make sure we have the best if everyone isn’t included?”

To direct the 2015 HBO biopic “Bessie,” about the Jazz Age singer Bessie Smith, she hired Dee Rees, then known for her lesbian coming-of-age film, “Pariah” (2011). Rees’s script emphasizes Bessie’s bisexuality and gender fluidity, as well as the distinctive approaches of women in an industry run by men. The blues matriarch Ma Rainey (played by Mo’Nique) negotiates her own fees with white businessmen, while Bessie’s husband (Jack Gee, played by Michael K. Williams) secures a recording contract on her behalf. Asked whether Compere’s maleness has opened doors for her, Latifah explains that he has at times helpfully presented “people’s idea of what a man is.” But she also says that she and Compere have worked with powerful women at every turn, from record executives to booking and film agents. “There is no hip-hop as we know it,” she adds, “without Sylvia Robinson,” who co-founded the first rap label, Sugar Hill Records, in 1979.

“The Equalizer” also brings together a group of loyal collaborators. Debra Martin Chase, who produces the series — and who also helped to create “Just Wright” — says that Latifah’s father, Lancelot Owens Sr., a former cop (he and Rita separated when Latifah was 10), hangs out on the set and advises her on fight scenes. The series also occasioned a giddy reunion with Pinkett Smith. “Let me tell you something,” says the actress. “La can come off as so serious, but La doesn’t want to do nothing but have a good time.”

The show has Latifah occupying a role first played by a white man, Edward Woodward, in the 1980s, then adapted by Denzel Washington for the film franchise that originated in the 2010s. Latifah’s Robyn McCall is a hero of citizens failed by the state; she’s “the one you call when you can’t call 911,” as the character herself puts it: a neighborhood superstar, to recall Danyel Smith’s phrase, like Latifah’s hip-hop persona. (You can tell she’s in charge in part because the makeup artists leave visible, as she prefers, the scar on her forehead that she got from wrestling with Winki when she was 3.) But whereas a young Latifah was both imperiled and propelled by rap’s cultural visibility, one of the pleasures of the show is to watch her fly under the radar in various guises (lawyer, fighter, chauffeur), relishing a mutability traditionally enjoyed only by white men. Still, network TV has its limits: Robyn’s Aunt Vi (played by Lorraine Toussaint) has a female lover — a queer story line the creators opted not to give Robyn herself.

ONE OF THE lessons of hip-hop, as the music turns 50, might be that revolutions are ever unfinished. The people who created the genre were the spiritual and literal descendants of the 1960s grass-roots activists who started their own community theaters, breakfast programs and free health clinics; who organized marches and festivals. Their children grew up in places like Watts and Baltimore, which were still underfunded and overpoliced. But they knew how to organize. They made a new form of music, art and dance, as well as the merchandise to promote it and the companies to produce it. (“Boy, are we businesspeople,” Latifah says. “How else do you think this happened?”) They bought homes for their parents — as Latifah did, at age 21, for her mother — when the banks wouldn’t lend them money. After Rita died of scleroderma in 2018, Latifah made a documentary to raise awareness of a lung disease that complicated her mother’s condition. She and Compere were behind Rise Living, an apartment complex in central Newark that includes 16 affordable housing units and is also meant to encourage higher-income residents to stay in the neighborhood. “Why not me?” is a question raised not only by ambitious creatives but also by citizens who decide to make change. “This was never something to keep to myself,” she says. “It was always something that was supposed to help change all our lives.”

It was also meant to be enjoyed. “I always wind up talking about social issues when it comes to my journey,” she says. “But I’ve gotta tell you, it was mostly a lot of fun.” At a tribute event for David Jolicoeur, a member of the hip-hop group De La Soul who died earlier this year, the D.J. played “Ladies First,” and Latifah summoned Love — “Monie, what’s up?” — to perform the song again. Ever her eager attendant, Love jumped at the chance, she says, feeling “the same excitement” as the day they wrote and recorded the track. Those who know her well say there are many reasons Latifah keeps hustling: a sense of mission, a lifestyle to finance. But above all, it is a blessing to have survived, and she’s still enjoying herself.

If we admire her without knowing her, it’s because she candidly shares stories about her formative years in lieu of news about her life. (She has dodged questions about her sexuality at least since “Set It Off,” but she publicly acknowledged having a partner, the choreographer Eboni Nichols, with whom she has a 4-year-old son, at a BET Awards ceremony in 2021.) Her second book, “Put on Your Crown” (2010), is far less forthcoming than her first, which detailed her grief after Winki’s death and her struggle to find the right man. These days, she says, “I share my whole life with the public. I share my gifts with you. I don’t have to share my personal business.” When she adds that she’ll never be intimidated by “some damn reporter,” it’s an oblique enough shot that we can bounce back from it. I think of a scene in “Bessie” in which the singer comes home after a concert and gazes at her reflection in a mirror in a darkened room. For all her love of a crew, Latifah has likely stayed sane by protecting her home life as well as her solitude. It was in these spaces of quiet where Dana Owens got to know Queen Latifah in the first place, and where she thought to ask, “What if they love me?” After decades of suturing worlds — Black and white, men and women — the space between private and public is one she refuses to thread.

BEFORE WE GO, I ask about a lyric from “The Light,” a 2009 song in which, after a roll call of great entertainers from New Jersey (including Bruce Springsteen, Sarah Vaughan and Frank Sinatra), she issues this encouragement:

You gon’ make it girl, you gon’ make it — fo’ sure!

Visualize it in your mind, then apply pressure!

… If you stay true to the cause, the world’ll believe

And you can say, “Mama, look at me!”

“I made it to the light”

Latifah sings the last line on an easy midrange loop like a lullaby. Yet the words seem to shift over the course of the track from “I made it to the light” to “I’m headed to the light” — thus shuttling between the pride of arrival and continued aspiration. But before I map this duality onto her whole career, I want to make sure I’m hearing it right.

“We could play it and I could tell you,” she offers. She’s already singing and rhyming while finding the song on her phone — “That’s some good-ass lyrics on that record,” she says — and I’m struck by both her pitch-perfect voice and her total recall of the track, which she recorded 14 years ago. I watch her, head down, phone to her ear, jamming out to her song.

Yes, it’s both “I made it to” and “I’m headed to,” but she adds more layers. “It’s also a divine thing,” she says. “It’s a blessing to be in the light. And to make it? It’s a one-in-a-million shot. It’s that Latin Quarters feeling. It’s looking at them on that elevated stage. They’ve got the lights and the mic and it’s like, ‘Just stay on your course!’” Here, in one of many intimate encounters with herself, she is addressing Latifah the teenager and using the memory of her early drive to recharge in the present. Then, as now, there was much more to come.

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.”