Lindsay Lohan: From Herbie Fully Loaded To James Deen Fully Loaded

Monkey500 by Monkey500 on Apr. 30, 2014

lindsay lohan blond wig in playboy

It can be easy to overanalyze the nature of celebrity and to scrutinize the celebrities themselves. That said, few have been under the microscope as pointedly as Lindsay Lohan. Her story is full of a few ups and lots more downs, with comparisons to watching a car crash in slow motion not too far off base. We can analyze the various reasons -- never having a normal childhood, having not one but two parents who will never win any “parent of the year awards,” and of course a slew of drugs and hard living. That she was once a squeaky clean child star makes it all the more a juicy tale. For those though with a penchant for low voiced redheads, especially ones who have been referred to by a former friend as having a “firecrotch,” there may be only one real question on their collective minds.

Lindsay lohan topless selfie


lindsay lohan wearing lingerie in bed


From a kid in movies like “The Parent Trap” to a sexy teen in “Mean Girls,” part of Lindsay’s appeal was that she seemed like a genuinely talented actress. Whether she will ever really get to be seen as more than a circus sideshow again remains to be seen, but perhaps the beginning of her descent into tabloid fever started in 2006.


It seems at this point she started partying hard, as well as not wearing underwear in public. The number of nip slip photos from this period, soon to be followed by pics of her getting out of cars and exposing her vagina, staggers the mind. By the end of 2007, if you hadn’t seen some part of Lindsay naked you were clearly living in a cave.

lindsay side boob

lindsay lohan white dress nip slip


Around this time she started her constant trips to rehab, checking in to clinics as often as most non-celebs do laundry. She also began doing photo shoots in various states of undress, but not really showing everything until a 2008 photo shoot for New York Magazine. In it, she recreated a legendary photo shoot of Marilyn Monroe’s, all the more increasing the likelihood that the young starlet saw herself as destined for a premature end. Even if she didn’t, stunned onlookers who at this point were so used to seeing her in the tabloids looking as if she had been up for days on drugs certainly saw the parallels.

lindsay lohan dressed as marilyn monroe topless

2010 found Lindsay posing for a spread in Muse Magazine, with lots of naked models appearing in what could best be described as a cocaine orgy.



A few months later, she posed for Purple Magazine in a series of photos that make it look like she’s peeing, wearing a crown of thorns, and rubbing herself suggestively.

lindsay lohan whtie dress modeling for terry richardson

In 2011, she received a million dollars to pose for Playboy, once again trying to channel Marilyn Monroe with a blonde wig and famous poses. At this point though, as she had been seen nude so many times and in so many places, there was much less hype than if she had done it a couple of years earlier.

lindsay lohan playboy cover

lindsay lohan blond wig in playboy


Despite the seemingly endless number of nude photos of Lindsay floating around, she’s only really done one film that features a lot of her nudity. 2013’s “The Canyons” generated a lot of press, as it came from an important director (Paul Schrader, who had written “Taxi Driver” and “Raging Bull”), a famous screenwriter (Bret Easton Ellis, author of “Less Than Zero”) and was seen as Lindsay’s chance to be taken seriously again. It was among the first films to be financed on Kickstarter, and despite a tiny budget, its pedigree meant it was bound to receive a lot of critical attention.

lindsay lohan looking rough

Equally notable was that her co-star was a bona fide porn star named James Deen, and advance hype told of possibly X-rated scenes. There is a foursome in the film, which eventually came out without a rating, but it was hardly the sex fest some had expected.  Although the film is hardly perfect, it does have some really interesting moments and a dreamy and quite distinct visual look. A NSFW clip can be seen here.

A famous article from The New York Times Magazine, which can be read here, detailed how difficult the shoot was and only enhanced Lindsay’s already terrible reputation as difficult to work with. The article is full of fascinating tidbits on the shoot, including this one that speaks volumes:

“Lindsay, you held the cigarette up in the last take, now you have it down. Let’s do it again.”

Lohan sighed. Now that shooting had begun, she had the power.

“Sorry, Paul, I guess you’ll have to fire me again.”

By midweek, Schrader and Lohan were locked in battle. One afternoon, he shot some of the lead-up to the movie’s pivotal sex scene. Lohan wasn’t happy.

"I hope you got my triple chin on that one,” Lohan said to no one directly. “That shot was hideous.”

Later that afternoon, it was time to rehearse a fight scene in which Christian physically confronts Tara over infidelity. Schrader tried to describe to Deen how he wanted him to throw Lohan to the ground. Deen nodded and went through the scene at half-speed. (It was a constant friction point between the two actors, Deen conserving his energy and Lohan demanding full effort in rehearsals.) After a while, Schrader cut in to show Deen what he wanted, lightly moving Lohan and turning her toward the floor.

“James, you see that?”

Deen nodded, but Schrader wasn’t convinced. So he grabbed Lohan, tripped her over his left leg and body-slammed her to the floor. Lohan screamed, and the crew gasped. But she bounced up with a smile.

“That was great! Want to do it again?”

Schrader said it wouldn’t be necessary. The next morning they filmed the scene for real. Deen came to life; throwing the negligée-wearing Lohan hard to the ground and pounding his fist into a wall with such fury I wondered if he had broken his hand. Lohan lay slumped on the floor, her hands guarding her face, shoulders shaking, tears pouring down her cheeks. Between takes, she listened to Ryan Adams’s cover of “Wonderwall.” After three shots, Schrader said he was satisfied, and Lohan fumbled for a cigarette. She headed downstairs, and someone complimented her work.

“Well, I’ve got a lot of experience with that from my dad.”


Here’s the official trailer:


As part of her umpteenth visit to rehab and the steps one is supposed to make, she made a list of her sexual partners. As she described on her program on the OWN Network, "That was part of my Betty Ford - it's step number five or step number eight. It's your sexual inventory."

lindsay lohans sex partner list

The list itself is juicy to say the least, and may well someday lead to a new version of Six Degrees of Kevin Bacon, as the list basically means that everyone in Hollywood is only a degree or two away from hooking up with everyone else in Hollywood. Among the many names involved are Ashton Kutcher, Ryan Phillippe, Heath Ledger, Evan Peters, Benicio Del Toro, Orlando Bloom, Justin Timberlake, Colin Farrell, Garrett Hedlund, Adam Levine, Wilmer Valderrama, Joaquin Phoenix and Zac Efron.

Although she swears it is all real, one high profile member of the list denies it vigorously.  James Franco, who admittedly was once a friend of hers, told Los Angeles Magazine “Lindsay herself has told lies about me with her people-she's-slept-with list!”

Considering that Franco is currently trying to enter the Guinness Book of World Records as the “Only Man who has done everything in the history of the planet,” it seems likely that his recollection is closer to the truth.