Lindsay Lohan is definitely in a dark place nowadays. She is cleaning up dead bodies at the L.A. Morgue and being escorted out of courtrooms in handcuffs. Her teeth are corroding and her skin belongs to a woman twice her age.

We have seen her grow up, we know her parents and how they have failed her. Her father was just arrested again and we know that she is not making good choices. Is taking off her clothes one of them?

Hugh Hefner has reportedly made a deal with Lohan to pose in the buff for "Playboy" magazine for a little less than $1 million. That is less than half of what she made washing her face five years ago for "Proactive" commercials.

Sure, it is a lot of money but for a former superstar it is just another depressing step down the rabbit hole. The "Playboy" nude spread is just something to do when there is nothing left to lose. "Playboy" is often one of the last stops before the train drops off in obscurity town.

On the other hand, not every celebrity model in the magazine has been captured on their way down. There are rare stars that 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 and so did "Bond" girls Kim Basinger and Ursella Andress.

There is a chance that Lindsay could be in the small group of women who have benefited career-wise from the exposure. However, Lohan might still continue to jeopardize her career if she does not get her act together and continue to make mistakes.