A decade ago, Madonna made a very good speech. She was collecting the 2016 Woman of the Year award from Billboard, and spoke about art, feminism, misogyny, and the mad few years when she was married to Sean Penn. She also spoke about dying. Or, rather, not dying. “People say I’m controversial, but I think the most controversial thing I have ever done is to stick around,” she said. “Michael [Jackson] is gone. Tupac is gone. Prince is gone. Whitney is gone. Amy Winehouse is gone. David Bowie is gone. But I’m still standing.”
This snippet of the speech does the rounds every few months on social media, as proof of Madonna’s self-aggrandisement. But in context, it’s quietly brutal: three of the names she mentioned hadn’t stood alongside her during her imperial phase (though she did, of course, date Tupac in the early Nineties), but the rest very much had. In fact, they were a quartet: Prince, Madonna, Whitney and MJ, four icons of the Eighties who invented the modern pop star, all but one now felled by addiction and mental illness. Madonna had outlived, and she was proud to have outlived. In pop music and beyond, it’s been the story of her life.
Even before the release of her death-tinged new record, Confessions II, I’d been thinking a lot about Madonna herself dying. It always seemed sort of unfathomable. Madonna has embodied an indestructibility – whether fuelled by ambition, spirituality, or some expensive Beverly Hills aesthetician – that seemed to say such mortal nonsense would never touch her. But then she nearly did die, in June 2023, from a bacterial infection so bad that her doctors placed her in a 48-hour coma.
From there, the hits kept coming: her stepmother died from cancer in September 2024, then her brother Christopher – a funny, sassy gay man who was by turns her best friend and her mortal enemy – died from cancer, too, a month later. Madonna’s older, more troubled brother, Anthony, had also died a few months before her own brush with death. Rumours surfaced last year that her 95-year-old father was terribly ill as well, but they proved unfounded.
Today, Madonna is 67. She is 11 years older than Abraham Lincoln was when he was shot. Cher kicked off her first farewell tour at the age of 56. Confessions II is not the work of an artist on the wane – it is full of urgent, glittering, often incredibly intimate disco-pop that neither panders nor cringes. It is, as has been written all over the place this week, her best album in at least 20 years. But Madonna herself is more fragile now, less steady on her feet. At a mini-gig in New York’s Times Square earlier this month, she slung her leg over a plastic barrier 30ft above the ground – but only after nervously jutting it back and forth to make sure it was safe. The Madonna of old wouldn’t have cared, gravity be damned.
“I’m tired as f***,” she told Interview magazine last week, admitting (gasp!) that she hadn’t worked out that day. “I have a bad knee now. I have no cartilage in it, thanks to dancing for so long in high heels and running on pavement and doing Ashtanga yoga. Up until a year ago, I was jumping on trampolines and doing dance cardio and doing a lot of what a doctor would call loading on my joints. Can’t do that any more.”
It’s been strange hearing her talk this way. While promoting her 2019 record Madame X, she rebuked the New York Times journalist Vanessa Grigoriadis for asking her about ageing (“I think you think about growing old too much. I think you think about age too much. I think you should just stop thinking about it”). She later condemned Grigoriadis on her Instagram, writing: “I’m sorry I spent five minutes with [her]. It makes me feel raped.” Thank God Grigoriadis didn’t ask her about menopause, as she had intended to. Madonna probably would have shot her.
The defensiveness was understandable. The press began spitefully dissecting Madonna’s appearance for signs of ageing in the early Nineties, then for signs of augmentation to conceal the signs of ageing in the Noughties. It’s slightly coloured how we talk about her age, as if to mention it at all is to jeer at it. But Madonna’s age – and her growing acknowledgement that she’s far closer to the end than the beginning – is rich subject matter, both in how she navigates pop stardom and in how it’s reflected in the music itself.
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Madonna’s 2023-2024 Celebration tour was a rare exercise in looking back for a star who once said she hates hearing her old tracks on the radio. It was a retrospective event filled with the original mixes of songs, many of which she hadn’t performed in years, and saw her properly cement her legacy on her own terms. She’s never liked other people doing that for her – just look at her cold and unsmiling reaction to Kylie Minogue handing her a vinyl of her first record last week on Graham Norton. “I look like I have a headache,” she complained of the artwork.
There was also her (now sadly aborted) film biopic, which seemed designed to contextualise her story and the sheer breadth of her involvement in art, music and pop culture over the last 50 years. Remember when she dated Basquiat while recording her first album? All of a sudden, Madonna seems eager for people to know how much she has mattered, as if she’s no longer confident we’ll memorialise her adequately ourselves.
Confessions II nods to her early days in numerous songs, but in ways that are tinged with sadness. “Danceteria”, the album’s funky, thrilling standout, is named after one of Madonna’s first New York haunts, a club on Manhattan’s West 21st Street, where she partied, found herself, and flogged her demo tape to anyone that mattered. It’s a breathlessly cluttered song, namechecking – in the style of that famously rapped middle-eight in “Vogue” – Basquiat, Keith Haring and David Byrne, and celebrating the sheer freedom of being young and ambitious in turn-of-the-Eighties New York. The album’s final song, the wistful “LES Girl”, recalls a doomed love affair around the same time, amid the excitement of her life properly getting started. “Lower East Side girl/ Lost in a fragile world/ The night is kind.”
But these stories collide with the tougher realities of where Madonna has ended up. On tracks like “I Feel So Free” and “Good for the Soul”, she boasts of still finding ecstasy on the dancefloor, but only because, off it, she is lonely, frightened, and distracted by the finality of everything. “It’s really hard for me to trust people/ Can you blame me? … That’s why I like to go dancing.” In a haunting duet with her eldest daughter Lourdes, called “The Test”, she sings about failing to realise how much her outsized fame would affect her children. “Sometimes I think you wish I’d go away,” she admits. And on “Fragile”, a song inspired by her brother Christopher’s death, she states – in a mournful spoken-word intro – that “energy never dies/ This is just a portal we’re going through/ Still, it’s hard to let go.”
I don’t think it’s a coincidence that Madonna’s best work in decades is her first work in just as long to properly tussle with her own mortality. When you’re the last one standing of a particular cohort of icons, and still producing new music long after they’ve all passed, you’re also tasked with laying the groundwork for how somebody grows older in the spotlight. There’s been no blueprint for that, just as there was no blueprint for being a shiny, sexy, boundary-pushing pop goddess before Madonna did it first.
For years – or at least, during her stretch of hit-and-miss albums from 2008’s Hard Candy to Madame X – Madonna leaned into her unflappability, rejecting or only lightly entertaining conversations about age, about fragility, about the end. Today, though, she has become fascinatingly vulnerable. Her physical strength isn’t what it once was, the people who knew and unconditionally loved her before she was the most famous woman in the world are dwindling, and the singular tragedy of her mother’s death – from cancer, when Madonna was just five years old – is now the first of many similar heartaches that have dented her.
I like this new Madonna. I like that she feels more human than she has in a while. And I like that she seems to be preparing us for the inevitable instead of pretending it’ll never happen – death comes for us all, whether we’re comfortably ensconced in a rest home somewhere, or parading about in hot pink corsets and fishnet stockings on live television. So why not head down to the dancefloor for a boogie while we’ve still got time?
‘Confessions II’ is out now
