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 lohan grey dress nip slip

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