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.