Poor Madonna. The master marketer, who's thrived as an entertainment powerhouse, on good press and bad, for longer than just about anybody—her first album came out in 1983—is now getting press that's mostly... pitiable.
She's always alternated between goddess and pop-cultural punching bag, but lately she can't catch a break. And we can't stop paying attention. Stories like
"Sean Pokes Fun at Madonna's Boy Toy." The Sean in that headline is, of course, eons-ago hubby Sean Penn, who, according to British tabloid
The Sun, ran into Madonna at a post-Oscars bash, gestured toward her 22-year-old male-model boyfriend, Jesus Pinto da Luz, and said, "Another kid already?"
And this:
"Madonna's the Same Age as Boy Toy's Granny." The Material Girl's latest fling is a media gift that keeps on giving.
This despite the supposed "cougar" trend—we're supposed to be cheering on older women chasing much younger men for a change. Turnabout is fair play and all that. The post-feminist twist on the timeless tradition of womanizing.
So why are we picking on Madonna for hooking up with an obviously desirable young man? What's wrong with being 50 and getting laid? So what if there's a whiff of desperation to the whole affair—who isn't desperate, in one way or another, these days? So what if it feels like too much of a marketing construct? I mean, really, Madonna and Jesus?
"Madge-Jesus Fling Is—Get This—a Sham: Pals," as the Newser headline put it, seemed a bit inevitable. But reports that Jesus's family thinks Madonna has "kidnapped" him are rather depressing. (Or, as Gawker’s Defamer column put it,
"Madonna-Witch Steals Child from Kindly Brazilian Couple.”) "I thought the whole thing was bizarre because it seemed like they were controlling him," da Luz’s former modeling rep told the
New York Post when he got a call not from da Luz, but from "Madonna's people," telling him he'd no longer be representing da Luz.
And let's not forget
"Madonna Converts Jesus" (to Judaism; he used to be Catholic). Given the reports last fall that Madonna's marriage to director Guy Ritchie disintegrated, in part, because of her control-freakery—
no TV in the house! low-fat smoothies for breakfast!—it feels retrograde, not progressively cougarrific, that she's now with a compliant man who, so far, has no voice at all. To the public, he's a pretty face and nothing more—a swarthier Jonas Brother or some lost member of Menudo.
Meanwhile, there's
Madonna's face, which the media can't stop obsessing about. “Hopefully, she’ll maintain at this point and not do more,” Suzan Obazi of the University of Pittsburgh’s Cosmetic Surgery and Skin Health Center told
ABC. “That’s what happened with Priscilla Presley—she kept putting more and more volume in her face and now has some severe side effects. Madonna should stop here.”

(AP Image)
In other words, there's a scary tipping point at play here, and we're all aware that Madonna's dangerously near it. Last summer,
New York magazine put an unsettling close-up of her on its cover, under the headline "The New New Face"—a piece about the latest face-plumping plastic-surgery trends. "There’s a new face in town—and it’s a baby’s." It's also vaguely creepy, clearly unnatural, and Madonna's the poster child for it.
The unspoken fear is that Madonna, like another pop star known for gravitating toward all things boyish, could go all Michael Jackson on us, plastic-surgery-wise. It's one thing to date a baby-faced male model. It's another thing to compete with him.
Until recently, those of us who never fancied Madonna's music could at least begrudgingly admire her as not only a shrewd entrepreneur, but an all-purpose rebel. But how are we to feel about a 50-year-old woman who, these days, mostly seems to be rebelling against herself?
Guest Off the Grid blogger Simon Dumenco is the media columnist at Advertising Age. Read more of his writing here. He can be emailed at dumenco@gmail.com