Lindsay Lohan is in a dark place. She’s cleaning up dead bodies at the L.A. Morgue and being escorted out of courtrooms in handcuffs. Her teeth are corroding, her skin belongs to a woman twice her age. We’ve seen her grow up, we know her parents, and how they’ve failed her. (Her dad was just arrested again.) And we know she's not making good choices. She's already naked professionally, stripped of PR protection. But does she need to take her clothes off too?

Hugh Hefner thinks so. He's reportedly made a deal with Lohan to pose in the buff for Playboy magazine for a little less than $1 million. That’s less than half of what she made washing her face five years ago for Proactive commercials. It’s a lot of money, sure, but for a former superstar it’s another depressing step down the rabbit hole.

She's tragic, an attribute Playboy readers crave. Famous has-beens are the pulp of the magazine readers' soft core diet. Their sex appeal, in part, relying on an audience's morbid curiosity. In the past decade, some of the biggest names to appear nude on the pages are former superstars and current retro jokes like Tiffany and Shannen Doherty. Then there’s the tabloid newspaper stars who lost their 10 minutes of fame, by the time they make the magazine. This year's crop includes Charlie Sheen goddess Bree Olsen and Levi Johnston’s sister Merecede. All share a common bond of being at that level of fame fueled by abuse. They're the people who lost the fans, and only gain new ones by becoming tabloid punching bags.

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The Playboy nude spread is just something you do when you've got nothing left to lose. Unless you're belong to the B-list "babe-lebrity" crowd (Denise Richards, Carmen Electra, Kim Kardashian) who only have to gain from the exposure, since their careers are built on semi-nudity. But for ex-superstars Playboy is often one of the last stops, before the train drops them off in obscurity-town.

Three years after she left Differ'nt Strokes and two years before she robbed a Las Vegas laundromat, Dana Plato did a spread. More recently ex-stars like Daryl Hannah and Tara Reid have traded nudity in exchange for sparking people's memory of their existence.

But not every celebrity model in the magazine has been captured on their way down. The rare star has used the magazine as a stepping stone: Drew Barrymore’s nude pictorial was the beginning of her comeback. In the '70s and early '80s, TV actresses like Suzanne Sommers and Linda Evans got a boost from the exposure. So did Bond Girls Kim Basinger and Ursella Andress. There’s a chance that Lindsay could be in the small group of women who’ve benefited career-wise from the exposure. One of those women, of course, being Lindsey’s hero Marilyn Monroe.

But Monroe also falls into the overflowing category of Playboy models who died tragically. Make no mistake, that group is depressingly large. Hopefully, there's no room in it for Lindsay.

This post originally appeared on Yahoo! Shine.

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