Lindsay Lohan Had Her Jail Sentence Delayed So She Could Pose for Playboy

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Lindsay Lohan is a big fan of Marilyn Monroe. She’s called Monroe her role model, bought an apartment where the late icon once lived, and has copied two of her naked photoshoots. One of those was for Playboy, and Lindsay Lohan was leaked all over the internet before the magazine had a chance to publish the magazine.

Lindsay Lohan Is a Huge Marilyn Monroe Fan


The first time Lindsay Lohan emulated Marilyn Monroe in a nude photoshoot was for New York Magazine. Photographer Bert Stern—the same guy who took the original photos of Monroe—came up with the idea. He said he thought “she had a lot more depth to her” than in “those teenage movies” that helped catapult her into tabloid fame. So, in February 2008, Stern returned to redo the shoot with Lohan, an homage to Monroe in “The Last Sitting,” from 1962.

But the world wanted more of Lindsay Lohan. The editors of Playboy pitched the idea to Hugh Hefner, who wasn’t sure at first.

“I kind of had mixed emotions about it initially, and then it turned into something bigger than life,” Hefner once told E! News.

Lohan Had Her Jail Sentence Delayed So She Could Pose for Playboy

If It’s Hip, It’s Here

However, the shoot got the green light, only to get halted in its tracks. Hefner didn’t like the way the pictures turned out and wanted Lohan to show more skin. Lohan apparently didn’t want to be fully nude originally. The Mean Girls actress was also getting ready to serve some time in jail. Luckily, a judge delayed her sentence for an entire week so she could get her $1 million Playboy photoshoot done.

“The pictorial and the concept for the pictorial came from me,” Hefner told E! News. “She had done semi-nudes before. I wanted to do something that would be memorable. So, what is more natural, since she is a huge fan of Marilyn Monroe, than do something that is a tribute to the red-velvet, Tom Kelley photo shot of Marilyn Monroe that was our very first Playmate?”

The result was a gorgeous red-velvet backdrop, fully nude, gorgeous shoot complete with Marilyn Monroe’s signature beauty mark. Lohan wore nothing but tan stilettos, baring it all with the same class and composure that the original Monroe shoot portrayed. The pictures were practically a copy-by-copy series of the originals. Shot by Yu Tsai, Lohan proves herself to be the perfect doppelganger for Monroe in 1953. At the time of Monroe’s Tom Kelley shoot, she was 27; Lohan was 25 when she redid them.

(Side note: Marilyn Monroe only made $50 posing for the original Tom Kelley pinup shoot. Playboy then bought the rights to the photos).

The main differences between Lohan’s Playboy photos and the originals are that the modern starlet went with the iconic platinum blonde locks that Monroe is usually known for. Conversely, Monroe actually sported a rare strawberry blonde hairdo at the time of her shoot. Also, Lohan’s breasts look gigantic compared to Monroe’s, which is surprising because Monroe was known for being so busty.

A Hacker Leaked Lohan’s Photos Online Before Official Publication

If It’s Hip, It’s Here

Lindsay Lohan’s Playboy shoot was originally intended to come out after Christmas, but a hacker had another idea.

The hacker, who kept his identity hidden but spoke to Fox News via a translator, said that he “just pieced it together.” He said he used peer-to-peer file sharing sites to gain access to 200 files. They were then published on, a site based in Russia, for purchase. The full interview and 10 photos were up on the internet, and it wasn’t via Playboy.

The hacker admitted that stealing Playboy photos was a hobby for them. They also said that in the past, Playboy had sent cease and desist letters, which they’d oblige. But with Lohan’s photos, Playboy went a different route. The hack caused such widespread interest in the shoot that, rather than hinder sales as feared, it may have just been a big accidental promotion. We probably won’t ever know, but either way, Hefner decided to publish the photos early.

Lohan’s shoot was released in the January/February 2012 Playboy magazine issue. That issue was then made available for purchase 10 days early.

“I think it was accomplished beyond anything I could have possibly imagined. People will not forget this pictorial,” Hefner told E! News. He added that the issue “became a stocking stuffer” because it was released prior to Christmas.

Read More: Dana Posed for the June 1989 Playboy Issue

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