How Miuccia Prada Reinvented Fashion

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.

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.

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.”