Lindsay Lohan poses nude as Marilyn Monroe

February 18th, 2008 // 467 Comments

Lindsay Lohan posed nude for a photo shoot with legendary photographer Bert Stern. Bert recreated an iconic photo shoot he did with Marilyn Monroe 46 years ago for New York magazine. Why choose Lindsay Lohan? Besides her “depth” (i.e. sweater cannons), Bert found similarities between the two actresses:

Stern, who shot the photos on film rather than digitally, told me he was interested in Lohan because he suspected “she had a lot more depth to her” than one might assume from “those teenage movies.” Indeed, many in the film industry believe that Lohan has yet to pursue projects equal to her gifts. Without putting too fine a point on it, you might say Lohan has, like Monroe, a knack for courting the tabloids and tripping up her career.

I don’t want to say Lindsay Lohan has a lot of freckles, but I don’t remember Marilyn Monroe having a topographical map across her chest. Also, Marilyn Monroe was reportedly drunk during the shoot while Lindsay is sober. Nice, Lindsay, how am I supposed to look at your breasts when you can’t even respect history? I guess I’ll manage – somehow. You’re lucky I’m a professional. Somebody fetch my boob-looking glasses.

NOTE: Pics are obviously NSFW. That’s code for “awesome!”

Photos: New York Magazine

  1. ahh

    Fuck you 97. Lol

  2. Chauncey Gardner

    She’s like a large, walking, vaguely-humanoid rash.

  3. squab

    I think she looks good with dark hair but in this shoot she looks like trailer trash Madonna in a dead cat wig.

  4. nipolian

    So who is the bigger has been….Lindsay Lohan or Bert Stern?

  5. Nita

    She look EXACTLY like Marilyn Monroe…………NOT

  6. jakebarnes

    I’m gonna chalk up the failure of these pictures to a washed-up photographer. It was a nice try, bud, but it didn’t come out too well. We all know Lohan can look sexy as hell in the right conditions. The right conditions these were not.

  7. Nita

    She looks EXACTLY like Marilyn Monroe……………….NOT

  8. BJ

    That’s what her tits look like at 21?! Jesus, I’d hate to see her in a few years when gravity takes more of a toll on this hag’s body.

  9. Chauncey Gardner


    What the fuck??? What the hell happened to that guy???

  10. Holy shit. I cannot get over how perfect her tits are.

    I hate Lindsay Lohan, i think shes a skank bitch that will sleep with anything that moves, but after seeing her topless I have to say I would definitely like to suck on them titties.

  11. Wow

    I am impressed how unattractive these make her look.

  12. she looks like a woman of 80th years old, I gues that this photoshoot is how marilyn should have look like right now or something!


  13. Lizzy

    Holy shit. She has the tired, bitter, seen-it-all eyes of an old lady and looks like she’s spent the first twenty years of her life in chamber filled with cigarette smoke.

    No actually, it’s worse. She looks like the old woman who climbs out of the bath in the Shining.

    A grievous insult to Marilyn.

    Pack it in Lohan.

  14. Lizzy

    Holy shit. She has the tired, bitter, seen-it-all eyes of an old lady and looks like she’s spent the first twenty years of her life in a chamber filled with cigarette smoke.

    No actually, it’s worse. She looks like the old woman who climbs out of the bath in the Shining.

    A grievous insult to Marilyn.

    Pack it in Lohan.

  15. jessica rabbit

    i’m way hotter than this bitch
    and my freckles are more appealing
    way to ruin it lohan

  16. Bo Babbyo

    I’m racking my widdle brain to come up with ways to have made this shoot more disastrous, but I can’t think of any. Every single photo I’ve seen of La Lohan up to this very minute has been more attractive than these, including the best of the worst of the Pap shots and her mug shots.

  17. norton

    I was really lookoing forward to one day seeing this chick naked…. now I have and I’m inexplicably turned off. Big time.

  18. Nordic Emulation - ha ha weep sons of pigs

    Why is it that EVERY woman, no matter what race, tries to have blonde hair? Is it because everyone knows that northern european women are indeed the best looking? You know, the REAL blondes!!!
    All of you losers are so owned that you are nothing more than my bitch property! AHHHHHHHHH haaaaaaaaaaaaaaaaaa haaaaaa!

  19. Bigheadmike

    She looks great!!!!!!!!

  20. mlk

    small nipples for big boobs. i’d hit it in spite of the freckles.

  21. Sun Damage Freckles

    Who wants to see Saggy tits that dont pass the pencil test?

  22. Arguman

    I’m a nobody who doesn’t look anything like Marlyn Monroe! He should have photographed ME in that wig! rrrrr >:|

  23. Heinrich Himler

    @118 Fuckin’ A right Brah! Aryans rulez! Hey man, when you actually visit a Scandinavian country send me a post card. Rock out with your swastika out dude!

  24. Ryan

    Fuck everyone who said her tits were fake. Those are big naturals.

  25. Dick Richards

    Hey, #118? The hair on my scrotum’s blonde — before I shave ‘em — does that make my cock Nordic?

    Even better: the hair on my choad’s blonde; does that make my asshole Nordic?

  26. Nazis and Nordics

    Not the same thing. Being teutonic is not a prerequisite for national socialism. But hey, nothing to be ashamed to be nazi either. Every other mutherfukkin cocksukkn bastard can be racist why not white people. We have zionist anti-defamation league, Azteclan, NAACP, you name it.
    I am not trying to be offensive, but all women wish they have blonde hair and blue eyes and it is a fact.

  27. Rut Roh

    The bizarre pink pic is nice.
    The freckles don’t seem to be the problem….The problem is her tit to hip ratio. She might want to consider hip implants, as I remember Marilyn having a banging hourglass figure, rather than Lohan having the body of a toady 14 year old boy with watermelons tacked to his chest.

  28. 125 Aryans only please

    As usual you are just not bright enough to follow a train of logic and are apparantly ignorant of anthropology as well as just about everything else other than dance and celebrity trivia and perhaps feltching old men.
    No having blonde hair does not make you nordic I mean in your case the blonde hair on your private parts most likely came from some big German dude ass fucking you.
    In your case it would be nor dick. Too easy, bitch. Back to the drawing board, shit tongue.

  29. costamar

    Marilyn would look better… as she is right now.

  30. Knight

    Damn… Trills have less freckles than that. Plus they looks better with them.
    Her boobs look photoshopped as they are the only area without freckles in that one shot that shows them off well.

  31. matt

    Trills, haha. LMAO.

  32. EuroNeckPain

    Just like Pamela Anderson’s “homage” was an insult to Brigitte Bardot, Lindsay Lohan’s photo shoot is an insult to Marilyn Monroe. What do they try to prove ? That women were far better looking and classier in the fifties/sixties ?

    Tonight, the Superficial looks like a damn Rocky Horror picture show. Only ugly pictures of crazy celebrities.

  33. drjay

    ya know. this isn’t half bad. despite lohan being a coked out attention starved nympho, this is still making the soldier salute.

    hey, at least she’s not posing nude like she was when she was stick thin and anorexic.

  34. 88mate

    Some airbrushing and she still looks GROSS. Other than big tits, what is the big deal?? Practically every girl I know that age looks better ie. don’t have skin like a 50 year old.

  35. Lisa

    Omg. I have never written a comment before, but I feel inclined to do so. I think she looks absolutely horrible in these pictures! I agree with #7, she looks rough, Marilyn was much softer, warmer and sexier than her. Under normal circumstances LL is an attractive girl, but these pictures are simply awful!

  36. 88mate

    Some airbrushing and she still looks GROSS. Other than big tits, what is the big deal?? Practically every girl I know that age looks better ie. don’t have skin like a 50 year old.

  37. TYtotheLOR

    i think she looks like shit

  38. TYtotheLOR

    i think she looks like shit

  39. mim

    For ONCE I have to agree.


    Get a real job Lindsay… your career was flushed down the toilet months ago.

  40. WTB

    I’m confused. Am I the only person who thinks her breasts are the WORST part of these pictures? Especially in the cover photo for this piece, she looks… well, saggy. She’s sagging. Like a 50-year-old. I’ve always kind of suspected she was secretly approaching her 50′s, I guess this confirms it.

    I mean, come on. Big breasts don’t need to sag unless you’re old or you haven’t been taking care of yourself.

  41. gre

    asco, para que ponen esa estrella?.

  42. Ok….first of all…freckles and blondes don’t mix. It just looks absolutely weird. So quit it…cuz it’s weirdin me out.

    Second…..look at the first black and white photo. Minus the yellow “things” tell me it doesn’t look like a corpse that just got pulled out of a drawer at the morgue…..on CSI. For real…I stared at it for a moment and she looked DEAD.

    She gives a shitty performance….even when taking pictures. Man…she sucks at life.

    Hey Lindsay! Next round’s on…..YOU.

  43. Sigmund Frodo

    Since I was a young lad, I’ve been mostly attracted to girls with freckles… love them! Irish and Scottish girls… yummy! If you hate freckles, why do you even bother looking at pics of the gals with them? Anybody that really loves boobs can tell that Lindsay’s have always been natural. She’s a natural beauty that looks best with her natural hair color. I find her candid shots, sans makeup, the best.

    That said…. just how old and senile is this photographer? The lighting is horrendous! She looks terrible in these pics!

  44. malicious

    why did she agree to this?? They could have done way better photos and i agree with 143 about the freckles and blonde hair.

  45. D. Richards (Nordic.. track.)

    #128? Are you trying to be sincere? Or are you just a fucking moron?

    I say sincerely moron.

    I like you: you’re one of those people that’s too dull to understand witt. You make my world go ’round, sugar. Thank you.

    Hey! Anthropology, man! Quief.

  46. meow

    Okay, she does look super fabulous. However, the most distinct difference between her and Marilyn? Marilyn had a real body and Lindsay still has the hips of a 12 year old girl. The only reason she can be considered a woman (physically) are the assets she had to purchase. Poor girl. Her body has more in common with Winona Ryder than Marilyn Monroe. She is very cute, though.

  47. D. Richards (Anthropologist.)


    Really: Weren’t you the orifice that said (n)ordics were the only ‘real’ blondes? So . . . if my asshole’s choad was a real blonde, wouldn’t that make the ass, a real (n)ordic? In your very much logical guesstimation, I think it would!


  48. c


  49. Lisa

    She looks terrible! I hope these aren’t going to be published…she’s certainly not that attractive and doesn’t hold a candle to Marilyn!

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