The Dead Get Nostalgia

Madonna and Michael Jackson are still everywhere. 
Which version depends on who you ask. ​

A friend of mine, someone I’ve known since college, recently found me at a rooftop party and started talking about his childhood. There were very few songs from that era, he said, that didn’t make him feel sad. But “Material Girl” was one of them. Maybe it was a space where he felt safe. He had yet to come to terms with his sexuality back then, and here was this woman who seemed unafraid of everything he was terrified of or maybe didn’t even understand yet. Or maybe it was simpler than that. Maybe it was just seeing an artist so unabashedly alive that the joy was contagious. Either way, his image of Madonna as something bright and positive from the 80s really meant something to him.

So I leaned in and asked what he thought of the early releases from her upcoming Confessions II.

“She needs to disappear,” he said.

I asked why.

“The new songs. They’re terrible.”

I pushed. What specifically? The production? The lyrics? The collaborators?

He paused. “Her face. What has she done to herself. Why is she behaving like this?”

And there it was. He wasn’t critiquing the music. He was revoking permission. The same permission his generation gave her forty years ago to be transgressive, sexual, confrontational, and weird. He just didn’t realize the expiration date was his to set.

This conversation stayed with me for days. My friend was not saying something unusual, he basically represented every Gen X and older millennial I know who once worshipped Madonna and now can’t stand to look at her. I literally went to Madonna concerts with some of them, female friends who now just cringe when I mention her name. This was in stark contrast to when I started talking to younger people about the same artist where things got interesting.

They didn’t flinch.

Not at the plastic surgery. Not at the sexuality. Not at the age-gap relationships or the provocative Instagram posts or the refusal to dress, behave, or exist the way a 67-year-old woman is supposed to. They found her music, liked it or didn’t, and moved on without the moral crisis.

At first I thought this was just generational apathy. Then I realized it was something far more structural.

This is a generation that grew up with FaceTune and filters. They edit their own faces before posting a selfie — smooth the skin, adjust the jawline, enlarge the eyes. Their mothers get Botox. Their fathers use Rogaine. Lip filler is a lunch break errand, not a secret. Ozempic went from a diabetes medication to a dinner party confession to a cultural shrug in under three years. Cosmetic modification isn’t scandalous to people who participate in it daily, digitally and sometimes physically, before they turn twenty-five.

So when they encounter Madonna’s face, the face that launched a thousand think pieces about women aging disgracefully, they don’t see a cautionary tale. They see someone who did permanently what they do with an app every morning. The scandal, to them, is that there was ever a scandal at all.

Consider what happened in June 2023. Madonna was rushed to the ICU with a serious bacterial infection. She was unconscious for four days, on a ventilator, and later developed sepsis. She has since described having a vision of her late mother asking her to come with her, to the other side, and saying no. She could barely walk to her own backyard for weeks afterward. She nearly died. And the public response from a significant portion of her original fanbase was to assume it was plastic surgery gone wrong. Another Joan Rivers. They’d already decided who Madonna was, a woman pathologically obsessed with her own appearance and they couldn’t process even a near-death medical emergency outside that frame. The face had become the only story they were willing to tell about her, even when the real story was that she almost didn’t survive.

The same generational divide runs through sexuality. Madonna dating younger men was tabloid fuel for decades. The word “cougar” was deployed like a diagnosis, something between a personality flaw and a public health warning. But we’re living in a post-cougar era now, and we’ve been living in it for longer than most people admit. Demi Moore and Ashton Kutcher happened. Kris Jenner and Corey Gamble — a man roughly the same age as her daughters happened. Priyanka Chopra and Nick Jonas happened. These relationships were tabloid noise for five minutes and then became…fine. Younger audiences watched these couples exist in public, on their screens, in their feeds, and the age-gap panic just quietly dissolved. Madonna’s sexuality at 67 isn’t transgressive to a generation that already processed this and moved on.

Demi Moore won a Golden Globe last year for The Substance, a horror film about a woman literally consumed by society’s demand that she stay young. The cultural conversation about what we do to aging women has already happened in cinema and the verdict was that the demand for disappearance is the horror. Not the aging itself.

And then, just weeks ago, the thing the film warned about happened to Moore herself. She walked the Cannes red carpet as a competition juror, and the conversation immediately shifted from her work to her body. “Skeletal.” “Too skinny.” Ozempic speculation. Eating disorder accusations from strangers who’d never met her. The New York Post praised her “toned arms” and was attacked for glorifying thinness. A woman who had just made one of the most acclaimed performances of the decade about the violence of body scrutiny got body-scrutinized at the festival celebrating her for making it. The culture watched The Substance, agreed it was brilliant, gave her every award…and then did to her exactly what the film said they would.

My friend at the rooftop was essentially arguing for the plot of that film without realizing he was the villain in it.

In 2016, Madonna accepted the Woman of the Year award at Billboard’s Women in Music and said something that I think about constantly. She said the most controversial thing she had ever done was to stick around. Michael is gone, she said. Tupac is gone. Prince is gone. Whitney is gone. Amy Winehouse is gone. David Bowie is gone. But she’s still standing. And earlier in that same speech she named the unwritten rule: “Do not age. Because to age is a sin. You will be criticized and vilified and definitely not played on the radio.”

She was describing something she’d already lived through. But she was also predicting what was coming.

And there’s a deeper irony in the names she listed. Michael, Tupac, Prince, Whitney, Amy, Bowie — every one of them has been liberated by death. The younger they went, the cleaner the legacy became. Nobody thinks about George Michael and that Beverly Hills bathroom anymore. They just make Careless Whisper videos on TikTok. Nobody dwells on Prince changing his name to a symbol and warring with his label for a decade. They just karaoke to Purple Rain. Nobody remembers “Crack is Whack” Whitney. They just dance along to “I Wanna Dance With Somebody.” Death purified the record. It froze these artists at the music and erased the mess. But Madonna, who survived and literally came back from the edge of death in a hospital bed and said no to the other side, she gets no such grace. She’s still here, still aging, still performing, still making choices that her original audience has to witness in real time. The dead get nostalgia. The living get scrutiny. What Madonna said in that speech
was far more powerful than perhaps even she knew.

What’s worth noting is who introduced her that night. Anderson Cooper took the stage and thanked Madonna for giving him faith during his years as a gay teenager. A closeted kid watching this woman be fearlessly, aggressively herself and thinking: maybe I can survive this too. That’s not fandom. That’s something closer to salvation. And it’s the same thing my friend was trying to describe at the rooftop. A kid who hadn’t come to terms with his sexuality found safety in a woman who seemed free in ways he wasn’t yet.

The generation that needed Madonna most is now the one asking her to leave.

But there’s another layer to this that I think gets missed in the discourse around aging and plastic surgery and sexuality. It’s about how we consumed celebrity in the first place.

My generation didn’t grow up with social media. We didn’t get to hear artists speak in their own voice every day, unfiltered, direct to camera. We got People magazine. We got the National Enquirer. We got Entertainment Tonight. We saw our icons through a lens and an interpretive mirror. Editors decided which quotes to pull, photographers chose which angles to publish, and tabloid writers constructed narratives that sold copies. The celebrity we fell in love with was always, to some degree, a manufactured version. And we internalized those manufactured versions as truth.

We are the generation that watched Oprah wheel out a wagon full of fat on national television to demonstrate her weight loss. We also watched her weight change again, and again, and again — her diets revealed, her lifestyle assessed, her body treated as public property every single time we stood at the grocery store checkout counter or bought a pack of gum at the bodega. The covers of People and Us Weekly told us what to think about her, and we mostly did. We didn’t have Oprah’s Instagram to hear her side. We had the tabloid’s side. And we thought that was the whole story.

The same thing happened with Madonna and Michael Jackson and every major figure of that era. We built our understanding of them through intermediaries — through journalists and photographers and talk show hosts who had their own agendas, their own lenses, their own reasons for framing the story the way they did. And then social media arrived and suddenly we could hear these artists in their own words, in real time, without the filter. But by then, many of us had already decided who they were. The tabloid version had calcified into conviction.

Younger audiences never had that problem. They met Madonna on TikTok, not on the cover of the Enquirer. They found Michael Jackson on Spotify, not in a courtroom sketch on the evening news. Their first impression wasn’t mediated by a magazine editor’s agenda. It was just the music. Just the performance. Just the art.

And nowhere is that generational split more visible than with Michael Jackson himself. His skin color changed in front of the world over the course of two decades. He went from the brown-skinned kid singing “ABC” to something the public couldn’t categorize, and the response was merciless. He was mocked on late-night television, pathologized in tabloids, turned into a punchline that wrote itself. The vitiligo diagnosis was treated as an excuse rather than an explanation. His eccentricity — the masks, the single glove, Neverland, the whispering voice — was reframed as evidence of something sinister rather than the behavior of a man who’d been famous since he was five and never learned how to be ordinary.

Younger audiences don’t carry any of that weight. They find his music on streaming platforms the same way they find anyone else’s. They watch the performances on YouTube and see a dancer who could do things nobody else has done since. Michael Jackson to them is the catalog, not the tabloid. And when they encounter the controversy — the allegations, the trial, the documentary that reignited everything in 2019, they process it with a sophistication that their parents’ generation never had access to. Not because they take it less seriously, but because they’ve grown up in a culture that has genuinely grappled with the complexity of separating art from artist. They’ve had that conversation about Kanye, about J.K. Rowling, about every problematic figure who built something people still love. They have frameworks for this. The older generation had only the binary of worship or rejection, and the whiplash between the two is partly why they’re so exhausted now.

This is the contradiction at the heart of legacy culture right now. The generation that built these icons — that gave them their visibility, that made them household names, that bought the albums and the concert tickets and the merchandise is increasingly the generation most uncomfortable with what those icons became. They want Madonna to age gracefully, which really means invisibly. They want Michael to have been normal, which really means uncomplicated. They want the version they remember, frozen in the cultural amber of 1984 or 1990 or whenever their fandom peaked. And when the artist refuses to be that version or can’t be, because time and life and the body don’t cooperate with nostalgia, the discomfort becomes judgment. The judgment becomes dismissal. The dismissal becomes “she needs to disappear.”

There’s a word for this that nobody wants to use: prudishness. The generation that celebrated Madonna for being sexually liberated can’t handle her being sexually active at 67. The generation that moonwalked in their living rooms can’t reconcile the man they danced with and the man they read about. They made the freaks and when the freaks refused to stop being freaky, they walked away.

But someone kept the lights on during those years of abandonment.

Someone kept streaming. Someone kept dancing. Someone kept the cultural temperature warm enough for a new generation to eventually walk in and discover these artists without the baggage.

It was the communities that mainstream culture spent decades dismissing. Gay fans who saw in Madonna a liberation theology that had nothing to do with the Vatican’s version — the same community Anderson Cooper was speaking for when he introduced her at Billboard. Black audiences who understood Michael’s genius without needing him to be uncomplicated first. The cultural “freaks”, people who lived outside the norms that the mainstream was now trying to retroactively enforce on the very artists who once helped them feel less alone.

These communities didn’t preserve Madonna and Michael out of nostalgia. They preserved them because the art spoke to something real about their own experience of being judged, being modified, being told they were wrong for existing in the body and the identity they actually had. When the mainstream generation moved on, these audiences didn’t. And their loyalty is the reason a 20-year-old today can find “Hung Up” on a playlist and hear it fresh, without the cultural trial that once came attached.
Yesterday, Madonna showed up in Times Square for a surprise pop-up concert sponsored by Grindr. She opened with new tracks from Confessions II, turned the LED screens to the Pride flag, flashed images of the 1969 Stonewall riots above the stage, and shouted “C’mon, gays! Happy Pride!” to a crowd that materialized out of rush hour foot traffic. No arena. No ticket sales. Just the Queen of Pop emerging from behind an LED wall on a Thursday evening for the community that never left her. While her original fanbase debates her face on Reddit threads, she’s performing for the audience that kept the lights on.

The corporate world, predictably, has noticed the resurgence and wants to monetize every angle.

Netflix’s Michael Jackson: The Verdict dropped this week, a three-part docuseries revisiting the 2005 trial through courtroom eyewitnesses, jurors, accusers, and defenders. This arrives while Antoine Fuqua’s Michael biopic is still in theaters, having earned over $846 million worldwide and now closing in on Bohemian Rhapsody’s $911 million record to become the highest-grossing music biopic of all time. Madonna’s Confessions II is weeks away, due July 3. The industry sees the heat and wants to harvest it from every direction, the celebration and the controversy, the music and the courtroom, the art and the allegation.
But here’s what the content strategists may not fully understand. A three-part docuseries about a trial that ended in acquittal twenty-one years ago is not going to change the way people feel about Michael Jackson. Not the younger fans who discovered him through the music. Not the older fans who already made their peace or didn’t decades ago. The legacy is grandfathered in.

The music was embedded in global culture so deeply and so early that no amount of re-litigation can extract it. “Thriller” preceded the trial by twenty-three years. “Billie Jean” preceded the allegations by a decade. The cultural infrastructure was built before the controversy arrived. And infrastructure, once built, doesn’t demolish easily. Try tearing down a cathedral because you have questions about the architect.

The biopic itself is proof. The film deliberately avoided the allegations entirely — its third act was restructured after a settlement clause prevented dramatizing the accuser, and the story ends with the Bad tour in 1988. It’s a celebration, not a reckoning. And audiences showed up in numbers that rival superhero franchises. They weren’t there for complexity. They were there because the music, the dancing, and the memory of what Michael Jackson meant to the culture is stronger than any further attempts to complicate it.

I keep thinking about my friend at the rooftop. His discomfort wasn’t really about Madonna’s face or Michael’s legacy. It was about the fact that the culture moved without his permission. He wanted the artists he loved to remain the artists he remembered. And when they didn’t, when Madonna got surgery and kept performing, when Michael’s story got messier and the world kept listening anyway, he felt something he couldn’t name. Not betrayal exactly but more like the loss of control over a narrative he thought he owned because he’d been there from the beginning.

But he never owned it. The generation that builds an icon doesn’t get to decide when the icon expires. That’s not how legacy works. The music outlasts the discomfort. The catalog outlives the controversy. And the communities that were never invited to the mainstream table in the first place — the ones who loved these artists through the years when loving them was unfashionable or complicated or inconvenient — they’re the reason there’s still a table at all.

​Madonna doesn’t need to disappear. My friend’s discomfort does. The music hasn’t changed. The face has. And the fact that he can’t separate the two says everything about his generation and absolutely nothing about hers.