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Madonna interviewed by New York Times

Madonna at Sixty
The original queen of pop on aging, inspiration and why she refuses to cede control.

Madonna at Sixty

he night before the Billboard Music Awards in Las Vegas in May, Madonna was sitting in the arena attached to the MGM Grand hotel, staring at a double of herself. The double, who was standing on the stage many yards away, was younger and looked Asian but wore a similar lace minidress and a wig in Madonna’s current hairstyle, a ’30s movie star’s crimped blond waves. “It’s always the second person with the wig — she wants to see it,” a stage designer said, adding that when she makes a decision, she is definitive. “Madonna wants 10 options, but when she says it’s the one, it’s the one.”

Madonna was observing Madonna to make sure Madonna was doing everything perfectly. Up on the stage set of a funky urban street with lampposts and a tiled bar, the double hit her marks and held a fist up to her mouth like a faux microphone for a rendition of “Medellín,” the on-trend, Latin-inflected song that Madonna would be singing. Madonna looked at a TV and assessed the augmented-reality part of the show, in which four additional virtual Madonnas, one playing an accordion and another dressed like a bride, would materialize in the televised awards performance out of thin air. Nearby, guys bowed heads and said cryptic things like “Where’s the digital key?” and “I need the alpha channel” to one another, tensely.

All the fake Madonnas ran through the song a few times before Madonna skipped enthusiastically to the stage. The sex bomb at 60 was slightly less than bionic and wore a Swarovski-crystal-encrusted patch over her left eye (“It’s fashion, darling,” an onlooker explained when I asked why she chose to wear it). Afterward, Madonna mused about something being off, and the next time she messed up the part where she stood on a table and gyrated her legs in and out in a move called “the butterfly” while popping her head in each direction. But by the third run-through she seemed ecstatic. “It’s so nice to see her smile,” Megan Lawson, a choreographer, said from under a black bolero hat, “and have it be a genuine smile.”

The AR part of Madonna’s performance was a feat, devised by some of the people who worked on this year’s Super Bowl, and the next night at the awards show she danced boldly despite the eye patch, which had to be difficult, peripheral-vision-speaking. But she wasn’t incorporating fireworks, a marching band and flying backup dancers, as Taylor Swift did; she didn’t hand out special bracelets to every person in the audience, then activate them to beam a thousand points of light, as the Jonas Brothers did; she wasn’t in a leotard and rolling around on the floor simulating a lesbian make-out session, as Halsey did, though the reason Halsey did that has a lot to do with Madonna doing it first. When the people in the audience lost their minds that night, they lost them almost exclusively for the K-pop band BTS, whose smooth hip-hop moves have birthed a million memes. For Madonna, they rose to their feet and took their phones out to commemorate “the time they saw Madonna” but seemed to scream loudest for the gyrating butterfly part, which was a little skanky, and that pleased them.

Madonna at Sixty

The pop-music world around Madonna has expanded in such shockingly strange new ways in the past couple of years that her precisely executed performance almost seemed too delicate (“Medellín” is down-tempo for a Madonna song; at the all-inclusive Mexican resort I visited over spring break, the poolside aerobics teacher played the song as a warm-up). Teenagers have always dominated pop, but now that most new music in the United States is streamed, how many times a song is listened to by one person counts much more than how many people listen to a song — and kids simply have more time to stream music than adults. When I checked the charts after the show, rappers born after President Bill Clinton’s election were in the top slots (Lil Nas X, Lil Skies, Lil Baby, Lil Uzi Vert). Older musicians had to pander to the teenage demographic or even younger; Swift’s new single, “ME!” sounded like a Kidz Bop version of a Taylor Swift single and actually featured her shouting, during the bridge, “Spelling is fun!”

Backstage, Madonna posed for a candid photo with BTS; later, people left comments like “LEGENDS MEET LEGENDS” under the photo on Twitter. Finding out that there were indeed people who believed that a K-pop band of 20-somethings was equal in legendary status to Madonna, not only the highest-charting female musician and highest-grossing female touring musician in history but also an artist who changed the pop-culture game forever, made me gag, to use a phrase from her heyday. Among my middle-aged peers — my female and gay male peers, mostly — she was still an object of fascination. My friends in the fashion business who used to take cues from her liked her new hats but not her jewelry and the eye patch. My old crusty punk friends, including an ex-dominatrix who now owned a restaurant, said: “Madonna’s hard-core! I want to know what she thinks about menopause. We need her back in New York.” And everyone wanted to argue about her claiming a seat at the contemporary-pop banquet past her 60th year — was it really all that significant, if Bob Dylan and the Rolling Stones played stadiums past her age, David Byrne was regularly performing across America and Bruce Springsteen was still at the controls of Bruce Inc.? Or was it a superhuman feat, particularly when set against her two closest contemporaries, Michael Jackson and Prince, each of whom exploded with her at the rise of video culture in the early 1980s and each of whom died early, and ignominiously?

It was depressing that the younger generation didn’t seem to have an understanding of the way Madonna had used her iron will to forge a particular type of highly autobiographical, uber-empowered, hypersexualized female pop star who became the dominant model of femininity across the nation. Without Madonna, we don’t have Britney Spears, Lady Gaga and maybe even Janelle Monae. The doubles she played with during each of her transformations — not only the religious Madonna but the virgin, boy-toy, material girl, dominatrix, dancing queen, mom, yoga mom, adopting mom and, now, sexagenarian claiming her space among artists two generations younger — were fun-house representations of conventional femininity. They refracted and reflected a future most of us didn’t know was coming before she showed it to us.

Just a week before the Billboard Awards, I went to Madonna’s embassy-size home on a soundless street in central London for an afternoon. The tan Georgian facade, absent of ornament, gave away no secrets. In the foyer that day, reflecting upon her renowned impatience with fools (her former publicist once explained, “She smells fear like a dog”), I found myself asking the woman who answered the door, “Should I take off my jacket, or should I just wear it?”

Then a figure descended a nearby set of stairs. I saw the nude leather heels first, her feet transformed into a fleshy weapon, then the whole person, who was extending her hand to shake mine. Despite unforgiving paparazzi shots of the work on her face, she was shockingly beautiful up close. Her face was heart-shaped, with her blue eyes set wide apart and a chin that still jutted out like Elvis’s. A slightly off-the-shoulder, full-skirted Marni dress showed off her ivory skin; she was like one of those porcelain figurines of a rural lady in her Saturday best that people used to keep in glass cabinets. The look was far from the wisecracking, gum-snapping, thick-eyebrowed girl of the 1980s who didn’t shave her armpits, but it was effective: It announced that she was still Madge, the British lady of the manor — except when she crossed her legs, she had the old punk-rock black fishnet stockings under her skirt.

Madonna at Sixty

She greeted me with a wide, tooth-showing smile that seemed genuine — we had met once before, about five years ago in a boardroom at her record label that I thought at the time had the most flattering conference-room lighting on planet earth. She announced back then that if I asked a stupid question, I had to take a drink of tequila, but if I had a smart one, she would drink. At one point, I wondered if she planned to fall in love and marry again. “Wait, what does romance have to do with getting married?” she said. “Stupid question! Down it.” Only later did I realize she had created a distraction and avoided the question.

Now she took a seat on a hard bench that gave her a few inches of height over my low-slung leather chair. This time the room was dim. She had a director’s appreciation for the nuances of lighting. The night before, she was at a photo shoot until 3 a.m., and unwinding took two hours more. She has had insomnia for decades. In the late hours, she read books like Carson McCullers’s “The Heart Is a Lonely Hunter” or Joan Didion’s “The Year of Magical Thinking”; she liked learning authors’ back stories and admired those with mettle.

She drank alcohol but drew the line at sleeping pills — “That’s a slippery slide to get on,” she told me, pulling a crossed leg toward herself and massaging her taut calf. “I’ve been doing back-to-back video shoots all night, standing in the freezing cold, for the past couple weeks,” she explained. I seized the opening to ask how she felt in her body these days. “You’re my doctor,” she said in a not particularly playful tone of voice. “I just feel tired.”

She was a single mom of six now. Her second husband, Guy Ritchie, was gone, along with what her spokeswoman at the time said was $75 million of her money — immortalized in her song “I Don’t Give A” with the lines “lawyers, suck it up/didn’t have a prenup.” The removal of this amount may have made the Jenga tower of her fortune shiver but not fall down. For the past few years, she has been in London less than in the hilltop village of Sintra, Portugal, where her son David Banda, 13, attended a top soccer academy and she became perhaps the world’s most famous globe-trotting soccer mom. She told me she wasn’t yet over the release of her last album, “Rebel Heart,” in 2015, which sold less than her others. The songs had leaked online several months early, far from perfection. “There are no words to describe how devastated I was,” she said. “It took me a while to recover, and put such a bad taste in my mouth I wasn’t really interested in making music.” She added, “I felt raped.” It didn’t feel right to explain that women these days were trying not to use that word metaphorically.

In Portugal, she said, she was lonely. I asked if she felt that way because she was living in a castle, which seemed like the most appropriate description of the 16,000-square-foot Moorish revival mansion I read she bought, but she shot back: “Let’s not get carried away. I wasn’t in any castle.” She said about Lisbon, “It’s quite medieval and feels like a place where time stopped in a way, and it feels very closed,” adding, “There’s a cool vibe there, but where I was living with my kids, I felt very cut off from a lot.” She summed up her days: “It was FIFA and my kids’ school and that’s it. I’m fighting with the plumber.” For a moment, she almost looked shy. “I really wanted to make friends,” she said.

One night, she visited a Frenchman’s crumbling home on the sea for an improv session, mostly of fado musicians. “There was a vibration there that was magical and palpable, and suddenly musicians started playing,” she said. They rose from couches to sing, from chairs to pluck a guitar. Listening to the variety of musicians, from Brazilian samba players and jazz quartets to a singer from Guinea-Bissau performing in Mandinka, she fell into a trance.

I listened to her describe how this scene had wormholed her back to her younger self, particularly the one that emerged in New York City in golden early-’80s downtown Manhattan. Studio 54 was over, punk rock had come and gone and D.J.s like Afrika Bambaataa were figuring out how to mash up disco, seminal hip-hop albums and electro bands like Kraftwerk before sampling technology had been invented. She was the Italian-American dropout from the University of Michigan, given the name Madonna at birth; now, she remade herself as a sexy, lovesick street urchin in pre-gentrification Alphabet City, surviving by checking coats at the Russian Tea Room and modeling in the nude for art classes.

At night, Madonna slipped cassettes of her songs to D.J.s at Danceteria and the Fun House. She mixed it up on the dance floor with South Bronx b-boys and graffiti-artist-musician-painters like her new boyfriend Jean-Michel Basquiat (she claimed when they broke up that he took back the art he had given her and painted the canvases black). Cindy Sherman was showing in galleries around town, spurring interest in self-invention with her photographs. “I felt she was doing some kind of parallel kind of work to what I was doing,” Madonna said. “I could relate to her. Becoming other people but still herself with a sense of irony, making social commentary.” Jim Jarmusch was tooling around Manhattan with his 16-millimeter camera and playing in a no-wave band. The Beastie Boys were devising a tongue-in-cheek marriage of heavy metal and hip-hop rhymes and recording their first record. AIDS hadn’t spread widely yet. When people talk about what New York used to be like, that’s what it was like.

Madonna at Sixty

The conventional wisdom is that Madonna became more famous than everyone else because she was dying to become famous. What set her apart was her bottomless maw of ambition. And over the years, her statements — “I want to rule the world” — supported this theory. Today she put it this way: “First of all, I wanted to make a living. I was tired of being broke. But second of all, all I wanted was a song to get played on the radio. That’s all I was praying for. One song.” In Portugal, she felt like a girl without that desperate desire, less brittle than she had been — playful, interactive, open to diverse influences, as she was in the past. “When I was living on the Lower East Side and I didn’t see many concerts, I knew about Debbie Harry and Chrissie Hynde and the Talking Heads and David Bowie, but there was no pressure for me to be anything specifically, to sound a certain way, to look a certain way,” she recalled. “That’s an important thing, because it allowed me to develop as an artist and to be pure, without any influences. What I try to do now is to remember that girl.”

Not letting the past interfere with the future might be as difficult for her as anyone who rose to a high level in a profession. I asked how she felt about her old hits. “If I’m in a car or I go into a restaurant, I’m out somewhere, and one of my songs starts playing, I just go, ‘Ugh,’ ” she said, “probably because I’ve had to hear it five billion times already, and I want to escape that.” Ambition was certainly part of what kept her going, but it didn’t seem to be all of it. When I asked her how much longer she thought she would make music and where she thought she would end up, she said, “Straight to the moon.”

Madonna’s catalog is primarily composed of declarative anthems, mini pop arias and songs about longing or lies or mental disconnection. In her love songs, she celebrated her object of affection, often described as an angel or celestial being; for someone so raunchy and blasphemous, sanctified tropes always seemed to find their way into the tunes. “Madame X,” her new album, her 14th, is darker than usual, though it also includes fanciful summer love songs. She experimented with musical genres like dance, fado, rap and Cape Verdean batuque and explored her anger over world leaders like Donald Trump “who seemed to be systematically removing all of our personal freedoms,” she told me. She visualized herself as a freedom fighter traveling the world to spread the gospel of love and anti-discrimination — fighting misogyny, homophobia, racism, guns, the rise of authoritarianism.

Some of “Madame X” was recorded in London, but she didn’t build a recording studio at home — “Horrible idea,” she told me, “my house would be shaking all the time” — though she had an editing facility for videos and film. “That’s good because I can drop in for an hour and then go back to see my kids, or go back to my other life, and not have to get into a car and go somewhere,” she said. “But it’s also nice to get into a car and go somewhere and get out of your house. Otherwise I would never get out of my house.” In her professional life, a small group of assistants, managers and dancers orbited her like moons. Though they liked to refer to her as “M,” thus expanding her domain over one of the alphabet’s 26 letters, this entourage, always the most honest reflection of a star, struck me as witty, sensible and self-possessed. They were pros who had learned not to fear her, or how to disguise that feeling.

The entourage helped accomplish her infinite professional goals, and she acted as a de facto cultural consigliere, taking them to museum shows and recommending books to read. I heard them say “She’s plugged into a different frequency” a couple of times. Madonna believed in following her intuition. I heard her describe meeting her collaborators as “the universe conspires to bring us together.” Guy Oseary, her charismatic manager of many years, said that once she completes an artistic vision, she moves on fully. “Every time we finish a project, it’s a clean slate,” he said. “I don’t know what happens next.”

To hear the album, I walked through dark-walled rooms with full bookcases and shrub-sized flower arrangements in divine red-pink-purple and down the stairs to her home screening room. Everything was perfect. The phone cords looked as if a sailor had coiled them. A silver teapot shined so brightly that I saw my reflection. The small square screening room, on the same floor as her gym, was like a Tiffany & Co. jewel box, but navy rather than robin-egg blue. Every surface was velvet. Footprints covered the carpet like brush strokes on a canvas; I imagined Madonna whirling around, stretching, dancing. A set of weights rested in a corner.

The art was even more striking. Madonna spent her first major paychecks on paintings. She had collected Frida Kahlo since the ’80s, mesmerized by the artist’s cool gaze, as well as geometric Art Deco nudes by Tamara de Lempicka and works by Francis Bacon and Salvador Dalí. Near the screening room, a print of John Lennon’s handwritten lyrics to “Imagine” hung over the toilet — an intentionally hilarious location — and large portraits lined the halls, not only of Lennon and Bob Marley but also Alfred Hitchcock pretending to strangle himself with a tie.

Madonna is short, and the art was hung low, for her own appreciation. She wanted to be face to face. “Confrontational — they’re hung in a confrontational way,” she told me. In the study, while we talked, she pointed to a photo portrait of East African warriors taken by a friend on their trip to Kenya’s Rift Valley. “The girls on the right are the bead girls, and it’s kind of like a mating ritual, and they’re singing. The girls are holding sticks up in front of the men, and they have to jump really high, and while they jump, they have to tell a story.” She continued: “But here’s the sad thing. When the boy turns a certain age, he has to leave his bead girl behind, and his wife is chosen for him.” She let me absorb this, then smiled mischievously. “I imagine there’s probably a few people who don’t follow the rules.”

It wasn’t hard to make the mental leap from Madonna regarding her museum-quality art collection as household icons to the manner in which many fans, including me, regarded her. In the 1970s, when Madonna moved to Manhattan, my mother, a pattern-and-decoration painter, took me on the graffiti-drenched subway each month to America’s first nonprofit cooperative women’s art gallery, A.I.R., which she helped found in SoHo in 1972. There, she and her peers introduced me to their vision of femininity — their deconstruction of the warping effect of womanhood. Some of the artists were political, like Nancy Spero with her paintings of phallic-shaped bombs and scrolls of archetypal feminine heroes, and Ana Mendieta, the performance artist whose sculptor husband, Carl Andre, was accused of pushing her to her death from their apartment in Greenwich Village (he was acquitted); today, in the #MeToo moment, young women have made her their own cult icon.

I first heard Madonna when I was 11. She was the opposite of what I had learned so far about what it was to be a woman. She was sensual and playful, and I loved the way she tied her tights in her hair to make a bow on top. She was Cyndi Lauper with sex, Duran Duran with New York grittiness. And suddenly everyone looked like her — everyone wanted to be her. My friends and I were virgins singing along to “Like a Virgin” without understanding what the word meant. At one of her 1985 concerts at Madison Square Garden, she wrapped herself in a white wedding veil and lay down on the stage, breathily whispering “it feels so good inside” into a hand-held mike, before hundreds of balloons fell from the ceiling. It was like being present at the big bang of girl-power pop stars. Girls didn’t feel the same way about Janis Joplin — they might have wanted to be her, even lusted for her, but they didn’t scream as if she were Elvis.

Madonna might not have initially wanted little girls as fans, but at first she seemed to cater to the demo just like the performers at the Billboard Awards, though she attracted a lot of criticism about corrupting little girls’ souls or encouraging teenage pregnancy with “Papa Don’t Preach.” When I told Madonna that I was at that concert, she wanted to know how old I was then and said, “Wow, that’s young.” There was a pause, so I asked how it made her feel when she heard people reminisce as I had — if she was proud or was unmoved because she had heard the same thing a million times before. “It depends on context,” she said. “I’m happy to hear I was a part of the beginning of your being woke as a female. That’s cool.” When she thought about it now, she didn’t think the concert was groundbreaking. “I mean, my belly button was showing,” she continued. “If I look back on it, I don’t see it as a scandalous concert at all.”

That was her first reaction, to diminish her impact, but she soon reversed herself. “A woman fearlessly expressing herself and saying, ‘I’m encouraging all of you to be independent, to speak your mind, to express your sexuality freely without shame, to not allow men to objectify you, to objectify yourself’ — I don’t know,” she said. “All of those things seemed like the natural way of where we should be going. And strangely, a lot of feminists criticized me for it, and I got no support from that group. They thought, Well, you can’t use your sexuality to empower yourself as a female, which I think is rubbish, because that’s part of who I am and part of me as a female and a human being, my sexuality. That’s not the only thing, that wasn’t my only weapon and that wasn’t the only thing I was talking about.”

For someone who gave liftoff to third-wave feminism and has spoken out against the patriarchy for years, Madonna hasn’t always toed the feminist party line, or stood in solidarity with women simply because they’re women. I was curious about her thoughts on the Hollywood movement Time’s Up — did she think an anti-sexual-assault movement would move into the mainstream in her lifetime? “No, that was pretty surprising,” she said. Miramax, the company Harvey Weinstein owned with his brother, distributed “Truth or Dare,” Madonna’s 1991 cinéma vérité documentary that was perceived as prurient and ickily voyeuristic at the time but prefigured the rise of reality TV (on camera, she called her boyfriend, Warren Beatty, a “pussy man” and later demonstrated oral sex on an Evian bottle).

“Harvey crossed lines and boundaries and was incredibly sexually flirtatious and forward with me when we were working together; he was married at the time, and I certainly wasn’t interested,” she said. She added: “I was aware that he did the same with a lot of other women that I knew in the business. And we were all, ‘Harvey gets to do that because he’s got so much power and he’s so successful and his movies do so well and everybody wants to work with him, so you have to put up with it.’ So that was it. So when it happened, I was really like, ‘Finally.’ I wasn’t cheering from the rafters because I’m never going to cheer for someone’s demise. I don’t think that’s good karma anyway. But it was good that somebody who had been abusing his power for so many years was called out and held accountable.”

She said it was not true that she had ever asked Donald Trump for a date, as one “John Miller,” Trump’s publicist, who Trump swears wasn’t him, told People magazine in 1991: “She called and wanted to go out with him, that I can tell you.” What she remembered was talking to him on the phone in Florida. “I did a Versace campaign with Steven Meisel at his house in Palm Beach,” she said. He kept calling to talk to her. “He kept going: ‘Hey, is everything O.K.? Finding yourself comfortable? Are the beds comfortable? Is everything good? Are you happy?’ ”

She said that Trump had a weak character but that this wasn’t a surprise for an alpha male. “They’re overcompensating for how insecure they feel — a man who is secure with himself, a human who is secure with themselves, doesn’t have to go around bullying people all the time.” What about alpha women, I asked? “It’s the same,” she said. “It’s good to be strong, but again, it’s always about, where’s that strength coming from? What are your intentions? What is the context that you’re using your strength in? Are you abusing your power? Women can also abuse their power. And if that’s also backed up by a lack of intelligence, emotional or intellectual, a lack of life experience, a lack of compassion, then it’s really a bad mixture.”

The great, unexpected part of Madonna’s career came during her seamless movement from selfish girlhood to selfless motherhood, from sexy punk simmering with barely concealed rage to earth goddess. In the mid-’90s, she was a star who seemed to fall in love and have sex the way most of us grab coffee (she once explained, “My pussy is the temple of learning,” and took lovers including Tupac Shakur and Dennis Rodman). By the late ’90s, she was not only a devoted mother but an ecstatic one, regarding the birth of her daughter Lourdes as a window on transcendence. “I feel like when my daughter was born, I was born again,” she told Oprah in 1998. She wore her hair loose, eschewed makeup, went to therapy, did ashtanga yoga, joined the Kabbalah Center. “Ray of Light,” the electronic record she gestated at the time, sold 16 million copies.

Not everyone loved her later phases, like her 2012 hard dance album “MDNA,” probably best experienced at a foam party on Ibiza, but as a middle-aged mother who liked shaking off the week in the club from time to time, I remained by her side. And she poured deep emotion into those songs too, whether she was in love or angrily out of it. Relationships proved hard for her. “I found myself as a wife, in both of my marriages, being as I think everybody is: You try to please another person, and sometimes you find you are not being who you really are,” she told me. “That’s the struggle, I suppose, of being in a marriage or a relationship, especially as a woman. We often think we have to play down our accomplishments or make ourselves smaller, so we don’t make other people feel intimidated or less than.”

As she grew older, she had young lovers, sometimes 30 years her junior. She experienced joy and wild abandon with her children. But she had two biological children and adopted four from Malawi, one of Africa’s poorest countries, amid a media frenzy; the country’s rules required foreign parents to live there for a year, which she had not (the country’s Supreme Court decided in her favor). Her youngest two children are 6-year-old girls, whom she adopted in 2017. She was aware of the doubling effect of children, the way they reflect back your strengths and deficiencies. “If somebody said, ‘O.K., you’ve got to give one thing up,’ I would say, ‘O.K., I’ll stop working,’ ” she said. “But they like that I work. They love to come visit me and watch me work. My older children, my son, he’s a painter, and my daughter’s a dancer and choreographer — I can see how my work has influenced them, though they probably wouldn’t like to say so. I like it. It makes me proud.”

This was a pleasant conversation, a moment of bonding. We were both older mothers devoted to our very young children, and managing to do it all despite the challenge of constant messiness and too little time (and with the benefit of hired help). She said: “I couldn’t survive if I couldn’t be creative as an artist, but in the back of my mind, I’m always thinking, O.K., what is my son doing right now? What is my daughter doing right now? I haven’t spoken to David yet. I’ve got to be there for them. When is her show? I’ve got to make sure I don’t have things planned. My head is in a whirl.” More professional women were choosing similarly — sow oats early, build a career, have kids as late or later than nature intended — but mothering six kids at 60 and, you know, being Madonna, took the trend to an extreme. She liked hanging out with other moms who had little kids, like her friend of 30 years, Rosie O’Donnell, who also has a 6-year-old. “She’s much, much, much more strict than I am,” O’Donnell said. “They could really be nightmares, and her kids are lovely, wonderful, beautiful kids.”

Madonna was determined to be the best mother she could be, but because she was Madonna, sometimes she could be hard-core about it. She took the responsibility seriously — it was almost a matter of reversing the historical record, making good on the promise of her own mother before she was snatched away. Madonna’s mother, also named Madonna, died from breast cancer when she was 5, sparking her survivor instinct and fathomless ambition. In her songs, she returns again and again to the loss. I noticed that on the cover of “Madame X,” she resembled Frida Kahlo, with arched eyebrows and a thin smile, and the title was written over her lips in black handwriting. The writing looked like stitches, and reminded me of an indelible autobiographical image from a 1989 Madonna video: a little girl attending a funeral and walking up to her mother’s corpse, then realizing that the mortuary had stitched her lips together — a ghoulish final silencing.

In “Truth or Dare,” Madonna lay on her mother’s grave and swooned for the camera; she was later attacked for exploiting the death. Today she talked about owning a particular Kahlo painting, “My Birth,” which was hanging upstairs. Kahlo was being born to a mother from whom she felt disconnected, and you could see Kahlo’s face coming out of the birth canal while her mother threw a white blanket over her own face to avoid bearing witness to her daughter’s birth. Kahlo made the painting after her mother died of breast cancer, too. “I love it,” Madonna told me. “I love how honest it is.” She liked showing it to guests. It helped her push some of them away.

The truth was that talking to Madonna, in this dim room, about topics other than her family became increasingly difficult. In recent years, she had zoomed to the realm of demigods hellbent on doing good, like Bono, and, combined with the continued devotion to kabbalah, she had become preachy. The onetime fallen Catholic whose video was condemned by the Vatican was now religious. I respected her charity work in Africa, and I was interested in her deep concern about the spread of misogyny, fundamentalism and homophobia, but she lost me when she spoke over and over about paradoxes.

She quoted one of the Kabbalah Center’s teachings — “Wherever there’s the greatest amount of light, there’s the greatest amount of darkness” — and explained the more she learned on her humanitarian travels, the more complex she realized the world was. “The funny thing is, the more you know, the more passionate you feel about life, and the more joy you feel, and the more inspired you feel, but then also the more disgusted you are with humanity,” she said, calling it part of “the paradox of life.”

The carapace of fame often conceals insecurity, so I tried to turn the conversation toward her grand influence, but she was like a cactus with spikes protecting her from anyone getting too close, particularly journalists. For years, she put boundaries between herself and the media — she had to in the pre-internet days, when people didn’t have the option of following her online, so they just waited outside her building. “It was like living in a golden prison,” O’Donnell said about Madonna in the ’90s. “There were bodyguards everywhere we went, and people would have no qualms about telling her to her face what they felt about her black hair, and she would usually go, ‘[Expletive] you.’ Nobody can imagine what it’s like to have that much energy coming at you all the time whenever you’re in public.” She added, “She keeps herself grounded by her charity and by her children, and that’s the only way to stay sane in the world of fame.”

There were times, Guy Oseary said, when Madonna didn’t want to have newspapers and magazines that wrote about her in her home. On occasion, she would discover she was involved in a scandal when she pulled into her driveway to find 30 paparazzi stationed outside instead of the usual three. Oseary had dinner with her when he was a young A.&R. man at her label in the early ’90s, turning her on to Hole and Rage Against the Machine. “Someone told me something about her, and I remember saying, ‘Hey, I heard that you … ’ and she was like, ‘Whoa, before you ask me the question, think about who told you,’ ” he said. “ ‘If that person is someone you trust or you find is solid, then ask me. You thought of the person?’ I go, ‘Yeah.’ She goes, ‘Do you want to ask me the question?’ I said, ‘Absolutely not.’ ”

Now, in the social-media era, the Greek chorus she had blocked out was seeping in, saying she was too old, washed up, out of ideas, finished. “It’s not that I engage with it, but it ends up going in front of your eyes, and then when it goes in front of your eyes, it’s inside your head,” she said. “It comes up in your feed, and then you get pulled into it whether you like it or not. So it’s a challenge to rise above it, to not be affected by it, to not get frustrated, to not compare, to not feel judged, to not be hurt. You know, it’s a test. Yeah.” She added, “I preferred life before phone.”

The immediacy of the criticism, that she held it as a tangible thing in her hand, seemed as though it had made her nearly paranoid. I realized I couldn’t ask her about anything as personal as menopause, but I had to broach the topic of aging: If I had followed her this long, where were we going next? The fact was that statements like “I’m going straight to the moon,” while inspirational, were not enough. I admired her for shaking off prejudice about what an older woman could be, for being creative, provocative and sexual over 60 — “It’s almost like a crime,” was the way she characterized it. She might have been doing all this for the younger generation, so that when Miley Cyrus was 60, no one would bat an eyelash if she twerked on stage. She had always been a pioneer. She told me she had sympathy for the way middle-aged women are confused by social media, unsure of how to project an appealing image without relying on the shortcut of youthful beauty. “You can’t win,” she said. “An ass shot will get you more followers, but it will also get you more detractors and criticism. You’re in that funny place.”

But I didn’t want to put an ass shot on social media, and I wanted more from her as an artist than I did from Cyrus. The political thrust of “Madame X” was inspirational, and I appreciated the way she used the record to beg for mercy from God. But I didn’t feel I was hearing enough of her real thoughts about her real life. And when I delved into Madonna’s promotional videos for her skin-care line, MDNA Skin, named after the album, I felt further from her than ever. In one infomercial, she put on the old wedding veil and announced that we should “marry” our skin. In another, she sensually drew a Beauty Roller, a black contraption resembling a sex toy, over her body — it was her old public-masturbation trick, but this time fantasizing about cellular rejuvenation. She sat on a panel about the beauty industry with Kim Kardashian West in which they discussed Madonna’s new mist made from damask roses and proselytized about the benefit of good lighting. Kardashian West said campily but also seriously, “I should just never go out in daylight.”

When we talked about aging, I was surprised when she turned the issue back on me. “I think you think about growing old too much,” she said later. “I think you think about age too much. I think you should just stop thinking about it.” She went on: “Stop thinking, just live your life and don’t be influenced by society trying to make you feel some type of way about your age or what it is you’re supposed to be doing.” I told her that’s hard to do, and she agreed. “We are a marginalized group, women. And just because it’s hard doesn’t mean you stop fighting against it or defying it or refusing to be pigeonholed or put in a box or labeled or told you can and can’t do things.” I felt a little foolish for thinking that she would want to talk to me about my own concern about aging, like an older sister. She was an icon, not a shoulder to lean on.

Fans love aging musicians not only because they are time-travel machines — they love them for those musicians’ defects, for the way that as long as they’re still creative, they hold a mirror up to our own aging and offer clues to where we are going. And if they’re your heroes and you’ve traveled a long way with them, you know you have the same defects. When Madonna literally controlled the light around her, when she applied her massive intelligence to beauty products, it was part of her way of maintaining control, of hovering above. But even if I had the same defects, of wanting to always be in control, I wasn’t Madonna — I can’t control the light around me, I probably wouldn’t attract young lovers, I didn’t want to rule the world. I was an old mom in the playground with Go-Gurt on her shirt.

Madonna was up in the sky most of the spring, moving between London, Portugal, Los Angeles, Israel and New York, where she stayed at her apartment on the Upper West Side, though she lost a lawsuit with her co-op over letting her adult children stay there without her. In early May, she did not attend the Met Gala, as she always does; when the cameras caught her at Kennedy Airport on the way to Tel Aviv, she placed what looked like a scarf completely over her head like a mask, then perched her sunglasses on top of the scarf, having a little fun with the moment.

Two nights before, she arrived at the Midtown Hilton to receive an award from Glaad, the nonprofit that advocates L.G.B.T. acceptance in the media. A screen flashed an inspirational hashtag for those maturing with H.I.V., #AgePositively. Men in tuxedos, including one with a pin on his lapel reading “Shoot Loads Not Guns,” chatted over a stereo blasting “Get Together,” her club hit about love on the dance floor. Anderson Cooper, one of three people who presented her award, said: “As a gay teen in New York City in the early 1980s, there were a lot of times that I couldn’t see a future for myself. I was scared and confused and often felt alone.” He added: “Through her, I saw that there was a community out there for me. There was a life waiting for me, for all of us — a life full of rays of light and full of love. And you know what? She was right.”

Madonna arrived, swishing through the crowd in a pair of red sunglasses. She took the stage as the goddess that everyone in this room expected her to be — a survivor — working in some comic relief by saying she wrote her speech after midnight with a Red Bull and cracking a bratty joke at the expense of the Bravo star Andy Cohen, who was also receiving an award. “Andy, you’re legendary,” she drawled. “I can’t say why.”

While she was becoming a “creamy smooth pop icon goddess,” she said, she lost many friends to AIDS, including her ballet teacher from Michigan and the artist Keith Haring. She described the disease destroying her locals-only scene in Lower Manhattan. “I saw people starting to behave differently toward people who were H.I.V.-positive or who had AIDS — not wanting to shake their hands or eat chips out of the same bowl or touch the same doorknob,” she said. “It made me sad. It made me feel sick. It made me want to kick everybody’s ass.”

Then she started talking about Malawi, where more than 70,000 children were living with H.I.V. I had never heard her make an overt connection between being unable to save her friends in the early days and the philanthropy she has done in Malawi, as well as adopting four of her kids, but now she made the link clear. She quoted lines from a new song on her record: “Life is a circle. Death and loss brought me new life. Brought me to life. Brought me to love.”

It was a little dramatic, but as she spoke, I realized what set Madonna apart: Her career had not only been about ambition, or ratcheting up achievement. It had been one long process of meaning-making, of understanding herself through her art. Some of it wasn’t for public consumption anymore; she might not tell us as much about herself as she used to. But she was always crafting a narrative, whether the story was about young women’s empowerment or biblical salvation, being reborn in sweat on the dance floor or in motherhood.

Most of us realized, as we aged, that we couldn’t make the puzzle pieces of our lives fit and made peace with that. Madonna kept reaching into the past to discover more and more about herself. There was no one truth, only the deepening of your own understanding. At one point, she said to me rhetorically: “What is the truth? Your truth when you’re 18 is not going to be your truth when you’re 28 or when you’re 38. Life is not black and white. It’s gray, and one minute you’re going to feel so strongly and believe in something so strongly, and then maybe you won’t in five years.”

New York Times