The sexy cover shot was leaked online Tuesday on the website The Insider.com. It shows Lohan, in just a pair of black heels, straddling a red plastic chair in the shape of Playboy's iconic bunny to strategically cover her up. The "Mean Girls" actress runs her hands through her long blond cascading hair.
Lohan will offer a more detailed look when she sits down with Degeneres Dec. 15, which will be her first media appearance since she served 4½ hours in jail for violating her probation. Her appearance comes just ahead of the January/February issue of the men's magazine hitting newsstands.
Her rep assures that the inside shots are nothing but classy.
"The pictorial is absolutely fantastic and very tasteful, and will be accompanied by an interview that will let readers see another side of Lindsay," Steve Honig told the New York Post.
Playboy chief Hugh Hefner said the photo shoot channeled old Hollywood.
"[It's a] classic tribute inspired by the original Tom Kelly nude pictorial of Marilyn Monroe," Hefner told the entertainment show "The Insider."
"It turned out very well. I would say that I had some reservations early on, but after a couple of false steps, everybody came on board and it's going to be very exciting," Hefner said.
Apparently, Hefner was not satisfied with the first round of images after Lohan's initial shoot in October. He had the actress return for a reshoot with "a new theme."
Lohan pocketed close to $1 million for the Playboy spread, according to TMZ .
The money will surely come in handy for the financially strapped starlet. But will it help jump-start her career?
This would actually be Lohan's second time posing nude. The first time was in 2008, when she restaged a series of famed photographs of Marilyn Monroe for New York magazine. The magazine's online traffic jumped significantly, but Lohan didn't see much improvement in her career and her negative rating for celebrity likability actually increased.
Other than easing her financial situation - Lohan's lawyer recently told a court she couldn't afford counseling - it's not clear how a Playboy spread will help her.
Click through to see other stars who have bared their assets in the magazine's pages to mixed results.