As much as it had millions of Internet pud pullers scrambling for their keyboards, talk about a massively blown opportunity. What were the editors of New York magazine thinking when they had Lindsay Lohan re-create Marilyn Monroe’s final photo shoot for their current issue? Actually, that one’s easy. As pyjama-clad perv Hugh Hefner learned long ago, there’s no better way to boost circulation than getting a high-profile celebrity to bare her knockers.

Monroe was a drug-addled alcoholic mess when she did her last shoot with photographer Bert Stern. Fittingly, Stern’s Lohan shoot finds the 21-year-old looking like a drunken alcoholic that Perez Hilton’s cat might have dragged in. Although T & A was the big selling point, on a deeper level the pictures were presumably meant to comment on the way the modern pop-culture machine chews up its young.

That’s where the golden opportunity was missed. As colossal a fuck-up as old Fire Crotch might be, she’s not even close to being the biggest mess in America. If you’re taking bets as to which modern celebrity looks set to join Monroe on the Boulevard of Broken Dreams, there’s only one tragedy worth betting the Prada purse on. Yes, it’s Britney, bitch.

Spears famously started off the year by taking her son Jayden and locking herself in the crapper of her Hollywood home for three hours as part of a custody battle. Like every tabloid in America, Rolling Stone subsequently ran a picture of a cackling Britney being removed by paramedics with her legs restrained. Stating the obvious, the magazine noted, “This just isn’t funny anymore.”

The condensed version of what went wrong goes something like this. A seemingly impossibly polite southern teen goes multiplatinum with an image that’s as prefabbed as the over-processed pop she traffics in. To millions of parents of tweenage fans, she’s the fresh-faced, waiting-for-marriage virgin, which doesn’t stop her from playing the Lolita-like cock-tease in videos like “…Baby One More Time”. But as much as Spears says all the right things, it’s all a lie. The eternal virgin has not only been riding rod since she was 14, she’s shagging Justin Timberlake, as well as the odd backup dancer. Impeccably mannered as she is when the camera is rolling, she’s burping, hideously flatulent trailer trash off-stage. Or, in her own words, she’s “southern”.

When the teen-pop empire finally crumbled at the beginning of this decade, the smart ones—Christina Aguilera and Timberlake—rebranded themselves. Spears stupidly decided to be herself. That’s perfectly fine; from Marilyn Monroe to George Michael, the celebrity highway is littered with people whose private lives have differed from their public personas.

Spears’s bad luck—besides being southern—was becoming famous just when there was a revolution in modern technology. Ten years ago, if you climbed out of a car with your snapper showing, only the valet got an eyeful. Now a girl can’t give herself a modified Riff Raff in a Toppy’s, go bat-shit with an umbrella, or chunder in a nightclub without someone catching it on their cellphone camera. Based on what we’ve seen of Spears, it’s obvious why her former BFF Paris Hilton refers to her as the Animal.

Nothing fascinates Americans more than watching their young crash and burn, which is why the current issues of Blender and Rolling Stone both have Britney on their covers. Never before in the history of pop culture have we had hourly Internet updates on one celebrity’s nuclear-powered free fall down the rabbit hole. Tragically, Spears has learned that being famous has never been a bigger bitch, especially when your MTV persona doesn’t jibe with your private one. Pill-popping waste case that she was, even Marilyn Monroe would have been lucid enough to relate to that.