Madonna: Cringe and Loving It
One must imagine the Queen of Pop happy... and that's what makes everyone so mad
By T. Bloom
It’s everywhere lately, and it started way before the Grammys: "Madonna looks so gross/scary now. Why can’t she just age naturally? I feel sorry for her."
You know, people have always thought Madonna was gross and scary. One could say those were the folks who truly launched her to stardom in the ‘80s, because literally everything she did or said ended up on the news or in the tabloids the next day, helping to spread curiosity about her brand of personal freedom to fans worldwide. To those who didn’t have cable or access to her music beyond the radio hits, she was almost like an urban legend, an MTV Pennywise luring America’s teens into the sewer of liberated sexuality.
When Playboy published her pre-fame nudes in 1985, the public focused on her natural body hair to an insane degree. When she highlighted androgyny, kink, and queerness in her performances, it was regarded (correctly) as an attack against restrictive societal norms, a glaring sign that corruption had fully infiltrated pop culture. Her irrevent use of religious iconography and her perversion of classic tropes of femininity were seen as an admission of guilt, a provocation of both lust and hatred.
And even then, a lot of it was couched in fake pity. "She needs help." "Something bad must have happened to that woman." "Anyone who wants that kind of attention is clearly disturbed.” Being grossed out by Madonna and pretending to feel sorry for her went hand in hand. It was a performance of one's own morality, but also a deflection — an easy way to distance oneself from the questions raised by her existence, her body of work, and (over time) her enduring popularity.
And now decades later, right at the time when Madonna’s fuel supply might have finally petered out, the same subspecies of onlookers are helping to gas her up again, propelling the Queen of Pop to a new reign over online outrage in the form of endless reaction videos and phony concern. Drawing back the curtain and willingly submitting herself to be harvested for the rage-clicks, hate-watching, and nasty comments that drive the media cycle, she has reawakened to haunt a new generation of children and their parents… like Pennywise in the second half of the series, I guess! “Drowned World”, indeed…
Of course, Madonna’s message of sexual liberation was far more accessible to the public the first time around, simply owing to her being a young, thin, beautiful white woman: America’s favorite object of lust and target of concern. Her eagerness to subvert that image by playing up her own monstrousness, her domineering, masculine, promiscuous side, turned many people off — or at least, they loudly insisted it did. (Had Google or PornHub searches existed back then, I’m sure those stats would have revealed a more complex truth.)
Observing the world’s horrified reaction to her was an education for young people who were awed and thrilled by this weaponization of femininity, so of course they followed suit and deployed it themselves, easy peasy! And the rest, as they say, is history.
By the late ‘90s Madonna stopped leaning as hard into the shock value, choosing to explore other aesthetics and fantasy realms. She’d started a family. She began to show signs of age, a popular subject in gleeful criticisms of her Evita performance. While she still enjoyed being provocative, it was easy to imagine she'd “grown up” a bit, that time had tempered her notorious desire to mash all of society's buttons at once — or that due to the expiration date placed on female pop stars, perhaps the world had finally managed to outlast her influence.
And that's when I think the "age gracefully" narrative around her really started in earnest. Would she do it? In the most patronizing and selfish way, that is the public's wish for any star of her stature: they want their untouchable icons to steadily morph into figures they can sympathize with and relate to, someone with whom they share a past and a common struggle, who is revealed to be only human after all (and whom they still kind of want to fuck).
So people loved hating her veiny arms — symbolic of the futility of athleticism in terms of outrunning age. Every new crack in her facade seemed like a triumph of the natural order of things, which are popularly imagined to align with conventional morality. Think of the warnings leveled at young people: "What about the future? You can't keep this up forever!" Reality may have a well known liberal bias, but time is imagined to skew conservative.
That’s right, whether or not one means it to, the act of “aging gracefully” can be understood as a capitulation to the inherently conservative expectations society has of women — expectations that are also enforced and embodied by gay men, perhaps now more than ever. And media entities, which are also inherently conservative, eagerly appeal to those instincts and anxieties, profiting from the manufactured moral panic.
All of this machinery existed before, in Madonna’s heyday. But now that she's not "young" at all anymore and her kids are mostly grown up, she's accomplished a major heel turn, stomping the accelerator right at the moment when most would hope she'd ease back entirely, as many of her contemporaries have.
But nope! She's back in full Cock Destroyer mode, showing off her juiced-up ass and bleached brows, tilting that aggressively tinkered-with face toward the camera in her budoir, adopting a super-sexualized party girl/space alien persona that seems specifically engineered to troll the haters: “U mad?”
And it’s working! Throughout her career Madonna has mastered two essential skills: knowing what makes other people feel icky, and doing exactly what makes her happy. Having all but forsaken contemporary American pop tastes in pursuit of touring and collaborating with artists abroad, she has less to risk than ever from crossing those twin streams and unleashing pure chaos.
While many lament it as a deterioration, or a desecration of her legacy, I think it's a renaissance — she’s now free to authentically lean into what was always monstrous, queer, and satirical in her art, all from the comfort of her home.
She has truly found the perfect amplification tool in TikTok. Nowadays literally anything she posts ends up triggering a tsunami of outraged, concerned, or mocking reactions. Even just showing her face (itself a brazenly deliberate creation) bumps her to the top of any given media cycle. To younger Puriteens and discourse-jockeys she's the perfect boogeyman, crossing over into their reality from a nightmare realm of sexual confidence and self-awareness they can't possibly relate to, and likely never will. And for their parents and grandparents, this must be like witnessing the resurrection of an age-old foe, one whom they failed to bully to death or effectively starve of attention the first time around.
But now they’re joined in their ranks by legions who may have once casually considered themselves Madonna fans, but whose appreciation of her broader message has failed to stand the test of time. And she’s a boogey for them as well, one who challenges the misogyny and ageism they’ve internalized over time, one who’s triumphed over fears of being “cringe” and is still out there having all the fun that no longer seems accessible to them.
Against this particular cultural backdrop, she’s once again reached a pinnacle of visibility driven by negative attention. She shakes her freshly-inflated ass and millions recoil in horror; she tosses some panties over her shoulder and alludes to being gay, and the internet goes up in flames. Playing around with filters and performing viral lip sync challenges inches from the front-facing camera, her antics are like a parody of youthfulness — but is the joke really on her, since she appears to be enjoying herself? Or is it on the steady supply of haters who keep elevating her visibility, fanning the flames ahead of her sold-out world tour?
So yeah, while I don’t adore her uncritically, overall I see 2023 Madonna as the apotheosis of what she's always stood for, but with a refreshing jolt of levity. And while erstwhile fans continue grieving the loss of a particular era or iconic moment that feels like their Madonna, they're missing out on the floor show of a lifetime.
It’s very common for young people to have a deep fear of their own sexuality, but I think in many ways older folks have it worse — there can be so much shame related to craving forms of pleasure that one is supposed to have outgrown, even if those desires never go away. We too are sensitive to cringe, cruelly evaluating ourselves not just on the basis of what’s hot with today’s youth, but also the particular sensitivities and judgments of those our own age, or older, whom we’re also judging. In moments when we fantasize about pursuing newfound desires, the ugliness of those judgments is reflected right back at us, chiding us back into place, those same words still ringing in our ears: "What about the future? You can't keep this up forever!”
That’s why older and younger generations alike have to imagine Madonna as unhappy and delusional, a woman who’s suffering from the lack of something crucial. The idea of someone being satisfied with the result of lifelong self-determination, transcending both pity and powerlessness, finding camaraderie in unabashed queerness, or even just enjoying a laugh at her own expense, is just too threatening. The possibility of pursuing joy on one’s own terms, even if it means looking like a wreck or becoming something that others will mock or revile, remains purely theoretical to most — a fairy tale that demands a tragic ending, so we can feel better and smarter about never having taken those risks, never tasting the forbidden fruit in the first place.
I guess in a sense, those who insisted she was weird and gross back in the ‘80s have been vindicated by Madonna 2023: turns out they were right all along! But they can no longer insist it was all a cynical ploy. And anyway, being weird and gross can be a lot of fun, and it’s often completely harmless. Many folks are even turned on by it, moreso than they might care to admit.
That’s the reality that our Pennywise of Pop has tapped into, and she’s feeling herself. U still mad?
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