NSFW Saturday: It’s Lindsay Lohan in Playboy, Naked!

Lindsay was paid nearly $1 million for this photoshoot in the January/February issue of Playboy. The pictorial was inspired by the Marilyn Monroe nudes by Tom Kelley that launched Playboy and Marilyn’s career back in 1953. And according to Hugh Hefner‘s Twitter, they are releasing the issue early online at iplayboy.com due to increased demand.

Also! Don’t forget to watch Lindsay’s sole promotional appearance on Ellen happening this Thursday, December 15.




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Jess is a pop culture junkie living in New York City. She enjoys endless debates about The L Word, Howard Stern, new techy gadgets, DVR, exploring the labyrinth of the Lesbian Internet, memoirs, working out, sushi, making lists, artsy things, anything Lady Gaga touches, traveling, puppies, and nyc in the fall. Find her on Twitter @jessxnyc or via email.

Jess has written 240 articles for us.


  1. I don’t know about the rest of y’all, but I’m legitimately interested in reading about when Steve Jobs met Andy Warhol

    • Yup. Sam was apparently quite *ahem* talented, according to Lindsay: (It is, after all, NSFW SUNDAY)
      @sevinnyne (Lindsay’s old Twitter account): your sweet sensual eclectic tongue is enough to LAST A LIFETIME!!!!!!!!! omgomgomgomg LILLY ALLEN IS THE SHITTTTTTT

      I just love her unabashed sexuality. Like, ‘Yes, I like having sex with chicks. And yes, I will tweet about sex with chicks. Thank you very much.’

  2. I didn’t even know that was Lindsey Lohan until someone said so… They photo shopped her so much.

    • same. ridiculous. The blonde look is also kind of off-putting (even if they are channelling Marylin Monroe, why does that have to mean look-alike).

    • I wish they hadn’t photoshopped her face so much. It’s white as a sheet. We know she has freckles. At least there are still traces of them on her body.

  3. My favorite is the last one. I quite like the full frontal one. The third one freaks me out a little bit because, in my opinion, she does look a fair bit like Marilyn. In that particular pose. I never saw any physical resemblance with her and Monroe at all before. But that third one, wow. They really got the angle right. I actually quite like the shoot in that it is very simple. I do love her red hair though. Ellen Von Unwerth shot my favorite image of Lindsay: http://suicideblonde.tumblr.com/post/1137687659/bohemea-lindsay-lohan-by-ellen-von-unwerth

    • Wow that image is amazing!! Never would have guessed it was her. Much like these photos. I miss her red hair so much

    • yeah despite anything else that has ever happened to this girl, she is an EXCELLENT model. i saw some show where she was drunk or on drugs at a photoshoot and a hot mess, but still when it was time for the shoot itself she worked it. it comes naturally to her, maybe. i’ve witnessed a lot of professional photoshoots, both personally and like, on tv or in movies or whatnot but i think she’ll keep getting modeling work even if acting dries up, and i think it’s because she’s a really good model.

    • Publishing really needs to let go of the Blur tool–her skin is so poreless and smooth that she looks like she’s made of the same stuff as a Barbie doll’s face.

      Her areolae are also an oddly pale pink, more a lip gloss color than a skin one–I think those may have made-up/digitally lightened some to go with the icy-pale skin that is not naturally hers. (For a redhead, her skin actually is capable of a bit of a natural tan along with the freckles, but it doesn’t go with the classic film star look they’re aiming for.) The rest appears to be faux-vintage graininess and lighting that does its level best to wash out her color (and her physical flaws) as much as possible.

      • Awkward comment, but as a redhead I would like to note that I have never been able to tan and the parts of me that don’t see the sun are as pale as in this photoshoot.

        However, it is clear that Lindsey’s been photoshopped. She is not this pale.

  4. Lindsay Lohan annoys me but phwoar…That is all….

    (I’m ignoring the fact of a strong possibility of air brushing)

  5. Is this a joke? Or real? I don’t see Lindsay Lohan here. Am I missing something? Or is this a Photoshop piece of phoney baloney?

    • Like I don’t really care if her boobs are photoshopped, surgically enhanced, or are benefiting from 20 yards of invisible tape because BOOBS. They look amazing.

  6. I wish she’d done her own photoshoot instead of a re-creation. This is still classy though, in an airbrushed kind of way.

      • weird I had thought the re-shoot was because Linds had tried to do a Marilyn thing, and Hef was like, nah, you’ve done that, let’s do something unique. I made that all up in my head but for some reason i thought it was quite possible. Guess I was wrong, I think I woulda like a Kate Moss inspired thing more. Though I’m not complaining.

  7. I think playboy shot someone else, and put LINDSAY LOHAN as a caption to get more attention and views because this does NOT look like her!

    • I had the same exact reaction.

      It’s a classy photo shoot, but airbrushed or not, she’s no Marilyn.

  8. It’s the make up. The make up artist did a really good job of imitating Marilyn Monroe. Her lips are drawn a little larger than usual, and with the cat eye sixties make up (plus photoshop) she looks a lot different. I’m seriously impressed.

    (Also, holy crap she looks amazing)

  9. I think I need a cock, a Bud, and gun rack to appreciate these pics… sorry. Just isn’t my thing. Give me red hair and freckles any day over whatever this is.

  10. i’m actually kind of glad that this shoot is more of a re-creation than anything else. something tells me that if the spread was too much like LINDSAY LOHAN NAKED it would have felt a little too close and a little too exploitative.

    • Yeah, considering how much of her image has become “YOUNG RECKLESS WILD CHILD” I suspect I’d be pretty skeeved if they went that route. Growing up in the spotlight has really been hard on her, I think, and I wish more people would remember how that kind of toxic environment and ceaseless pressure warps people.

  11. Hmm…I think they are good, but it’s just weird. Why is she so eager to be Marilyn, why won’t she just become her own icon. I most definitely liked her better as a redhead.

  12. I love it. I just want her even more now.. :)
    I don’t think she looks overly photoshopped. It captures the dreamy feel of the original shoot, and it shows of her amazing body. And well boobs! :)

  13. It’s…. not… relavant to my interests. I mean I appreciate blondes, but she looks so much better red. Also also also the amount of ‘shopping they did on her is like whoa and the boobs are either uber shopped or were purchased *ahem*.

    Sorry, all the pics on the the ladygay tumblers are so much more sexy to me. Also Kat Dennings.

  14. Since this is a tribute piece, I understand why they downplayed Lohan’s
    features ( freckles, tatts, etc..)
    Still, I think she looks stunning…
    Go on with your bad self, LiLo!

  15. I would not have thought that my first time commenting on Autostraddle would be on a Lindsey Lohan piece, but I’ve just got to let the world wide web know:
    I actually know her brother, Mike. We’re not good friends or anything, but we interact pretty regularly. And it is SO. WEIRD. now every time I read a Lohan article. Because now she’s not a celebrity, she’s that dude I know’s sister. And that is SO. WEIRD.
    But I’m still gonna look at the pictures. For, um, reasons.

    • this may be creepy, but my itunes on shuffle happens to be playing “portions for foxes” right now. just seemed like too weird of a coincidence not to share.

  16. Anyone who is a big fan of Marilyn Monroe should go check out the new film called “My Week with Marilyn.” I went to go see it last night and it was a great movie! Second, i prefer to see the actual Marilyn…not someone who tries to go for “the Marilyn look”. She was her own star and can’t be imitated.
    But i give Lohan props for trying. lol

  17. I think Lindsay is an excellent model and even with photoshopping you can’t just invent that sort of body awareness out of thin air. I do think a cool idea for the shot would have been the icon Marilyn stuff but with red hair instead of the blonde. But I supposed Lohan has been blonde for a while now.

  18. a) SamRo is singing “Angel in the Centerfold” right about now. I have always wondered what it would be like to date someone who goes on to do porn. SAMRO KNOWS.
    b)Lindsay is so soft. They Photoshopped her freckles away, but they didn’t give her any muscles where there was only downy, corruptible flesh.
    c)I wish Lindsay would stop doing tacky photo shoots like this for money. Doing Monroe TWICE? Like, seriously, half of Tumblr is classier than this.

  19. LL really is a good model. She definitely knows the poses and how to move her body etc. But there’s just something about her eyes in most of these photos that looks a little vacant. Tyra needs to teach Linds to smize.

  20. I just…don’t care. Really, I’m so tired. I don’t want to see/hear anything else about Lindsay until she dies from an overdose, like she will inevitably do/

    • I’m sorry. I don’t mean to annoying. But I just really dislike comments like yours. People said that with Amy Winehouse and now Amy is gone. It’s fine to say you don’t care to hear about someone anymore…but to say you don’t want to see or hear anything ‘until they inevitably die of an OD’ is just…imagine if you were Lindsay and you came across that about yourself? ‘I don’t want to hear about LezGreek until its her obit for an inevitable drug overdose.’ I understand you are probably not a public figure and you are commenting on a public figure. But…
      /end rant

      • AJS, I agree with you completely and your post doesn’t read like a rant. Please don’t apologize for your reply, it is great. LezGeek’s post was horrible, she should apologize.

    • Yeah, this post of yours sucks. Makes me sad to see it here.

      As for Lindsey… ff anything, I’m sad that her life has gone so far downhill, and I’m sure that many things led to it. Life as a child star is hard, and it only gets harder when one grows up surrounded by leeches.

      But rather than wish her ill, I hold out hope that she can get herself together and become a great person again. It will be hard, since almost inevitably, she’s surrounded by people that want things from her, and its easiest to get things when her life is in such turmoil.

    • If you don’t want to see/hear anything about Lindsay you probably should stop clicking on stories with her name in the title.

  21. For a million dollars, I’d gladly be naked, blonde, and photoshopped too.

    And eagerly awaiting the day I could spend twenty of those dollars to see Lindsay at the movies again. You go Lindsay Coco.

  22. oh my goodness in the very first picture her chest and her left leg are so very photoshopped. One does not even need to take a close look to see it. It bothers me how much shopping they did.

  23. I think her nipples acutally have a color similar to this. If you ever come across pictures of her accidentally losing her bikini top in the waves (I only read InTouch at the doctor’s office, I swear) they look a lot like this and those pictures are usually not as photoshopped because they are meant to show some kind of ‘ugliness’. Which they don’t, her boobs are hot!

  24. She’s hot, but I’m disappointed. Totally doesn’t look like her, or even a real person. Her boobs are fanfuckingtastic, but everything else is just so off-putting that I can’t properly enjoy them.

  25. Can’t believe my first time commenting on an article here happens to be about Lindsay Lohan.

    Hugh Hefner made a mistake by getting her to channel Marilyn. She would have been so much more gorgeous with her red hair and freckles. oh yes!

  26. I’d like it more if she looked like Lindsay Lohan. Man, I’ve loved her since Parent Trap. I’m glad I’m not the only one who still hopes she pulls through and does awesome things.

  27. Never thought I’d say this about Lindsay Lohan post-2006, but I’d hit that. I have to say, I desperately miss her red hair. :'(

  28. i think she looks unnatural and i wish she’d stop harassing/ channeling/ whatever marilyn monroe’s memory and image. she had her own and she was a really beautiful, shapely, freckeley redhead. i like all the photoshoots linked in the comments where she looked more like herself then someone else.

  29. Fuck it I am just going to say it:

    I really do feel that the patriarchy fears full agency of female sexuality. I like that Lilo (assuming this a sober choice, ugh, this disclaimer is annoying given her history but we love context!!!!) chose to do something like this (better than hustler or penthouse imo). I don’t know nude women are like a “ohh, gawd-daaaaaamn” and “and the water is wet, she is nude” and I really feel that Lilo is doing something I hope BOTH female and male actors (anyone really) do in hte future: pose in confidence their bare naked bodies.****

    ****I am (probably) not sober typing this comment but dammit when I read this in the morning I will still stand by it.

    • I could say a lot here, but I’m just going to sum it up with this: females who idolize Marilyn Monroe remind me a lot of men who idolize Scarface: they both seem to focus on the fast life and high living, and miss out on the fact that their idols ended up dead of very unnatural causes.

      Was way hotter back in the Mean Girls days. Vanessa Hudgens on her worst day puts this skank to shame.

  30. I think she looks bizarrely like Rose McGowan, with the dramatic make-up & deathly pale thing. Not that I dislike that look, but both of them are, in my opinion, hottest with their freckles showing.

    Also, the part of me that used to have a big ol crush on Lindsay is kind of sad at how many times I have seen photos of her breasts. My inner adolescent’d kind of prefer that to be something I’d have to pause a dvd for or something along those lines, an event precious for its rarity. I never expected to be vaguely bored by Lindsay Lohan’s breasts, but here we are.

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  32. jeez she could at least work out a little bit before the shoot. meh, flabby and boring looking. i wonder if her boobs are real

  33. WOW This is so Photoshopped/ airbrushed… Why does anybody gives a rats azz about this talentless hack?? Lindsay go fricken kill yourself like Amy, you white trash whore..

    • Wow it makes me sad that people like you exist. Go back to one of your snarky, b*tchy hetero gossip blogs. So glad that autostraddle is mostly free from shallow, superficial commenters like this

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