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
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  1. theShizann

    FAIL!

  2. Judd G

    Does Lindsay have one freckle for every load that has been dumped into her puss or ass?? If so, I’d like to add a couple of freckles….on her face!!!

  3. Natanya

    You can see the line for the wig in the last one! Jesus.

  4. Cosmo

    Oh, I’d totally hit it, but I’d hate myself afterwards.

    And it reminds me of a joke I heard once: “What would Marilyn Monroe be doing if she were alive right now? She’d be trying to find a way out of her casket.”

  5. Natanya

    You can see the line for the wig in the last one! Jesus.

  6. The ass tat says “la bella vida”.

  7. Spazz

    She is ugly as fuck. Nice cans though.

  8. kate

    these pictures are a terrible recreation.

  9. The Office Whore

    good one mike! You’re smart! smart smart smart! s-m-r-t!!

  10. lmao

    LMAO @ PIC 6.
    WHAT IS THAT TROLL DOING?

  11. I have to say, the last one is okay. She doesn’t look too bad. She does have the world’s smallest nipples, it would seem. Smaller than most mens’ even.

  12. If only Mike could be the same..

  13. justifiable

    Double initials don’t make you an automatic sex symbol, LL, more like a bad joke. It’s not the freckles, it’s the desperation that’s ugly. Not to mention the pretension and delusion.

  14. deaconjones

    I have that same wig and wear it when I play tuck the peepee.

  15. Racer X

    I’D HIT IT for a $1000, Alex.

    /2 clicks = nipple

  16. Chris

    EEW!

    EEW!

    EEW EEW EEW EEW EEW!!!!

  17. grossed out

    yuck. extremely unattractive. she looks like a tranny.

  18. cruan_mobay

    I’m a straight guy but dude, I’d rather masturbate to photos of Andy Dick than those. Gross bitch.

  19. kitty_kat

    @17- “Marilyn Monroe” and “class” don’t belong in the same sentence…

  20. christian

    ALL OF YOU…..GE A LIFE

    AND FISH,,,GET A REAL JOB

    BTW THE CUNT LOOKS DECENT

  21. logic

    Her belly always reminds me the pillsbury dough boy. She has this permanently bloated, no waist definition thing going on. Seriously I amno Marilyn fan but, Lindsay doesn’t even come close. Marilyn had a stunning face (could have used a workout in my book) but, Linsay’s little frekled covered face and clown applied lipstick to make her thin pout look bigger is a total joke compared to Marilyn. On top of it back in the day they didn’t have all the fancy lighting, plastic surgery, spa treatments, fake tanning and airbrushing techniques that they do today so this is actually pretty sad, I’m almost embarrassed for Lilo and her saggy tatas.

  22. Auntie Kryst

    Haaaapyyyy Birrrrthdayyy Mr. Presi…Fuck it, I can’t go on. Lohan is a fucktard! Get me my whiskey!

  23. Harry

    Methinks someone’s desperate to jump start their career. At least she didn’t wait until she was 50 to do this. Next stop, Playboy!

  24. Ariel

    What?? Okay, I’m not exactly a fan of her ginger-kid-posing-as-california-blonde-with-vomit-orange-tan look, but she can look so much more attractive than this. It doesn’t even look like her.
    Cheap-looking wig, bad lighting, unflattering poses. She looks more desperate than iconic.
    And what’s the deal with every insecure, daddy-deprived slut in Hollywood under the age of 30 worshipping the insecure, daddy-deprived Monroe? Yeah, she was blonde and hot, we get it. But so were dozens of other women in that era who were honestly more interesting and worth admiring.

    Whatever, these picks are fug. Ginger fail.

  25. Sauron

    Marilyn Monroe was the most intelligent dumbest bitch in the twentieth century.At least Lindsay has halfway something in common.

  26. lipper

    Her poses are just awkward! Or is it the vapid bored look that makes this so dull?

    It’s just off somehow. Or she really IS that boring, I think its poorly done and that editor needs shot.

    I like that she got rid of her implants, those are suppose to be real, and with the natural slope I do believe they are. And those are hot, I’ll give her that. HATE fake tits.

  27. kitty_kat

    I agree with 7. All of her flaws are accentuated. And if she wants to pose nude and look good she’s going to have to gain a little weight so that she actually has a waistline.

  28. Sebastian Melmoth

    I am loving all this dislike towards her. It keeps the line shorter.

    I’ve never even heard of NY Mag but I just ordered 2 copies of this issue.

  29. I'm Yer Daddy

    Close but no cigar.

    And by close I mean a trilllion miles away and by cigar I mean an errect penis.

    Bitch is fug, I’d take Marilyn’s decaying corpse over this nasty ass and I never found Marilyn hot but, she a goddess compared to this untoned skank. Her stomach looks like a dead seabass. Fucking nasty.

  30. sindiva

    have any of you seen the original? Marylin didnt look amazing in most of the shots, she looked tired and clownish. And she had freckles- DUN DUN DUNNNNN

  31. veroonica

    33. It spells out N-E-X-T!

  32. whoa

    well, she’s peaked. it’s all downhill from here.

  33. steve

    Hey everyone, what’s the official word? Are those breasts real? If so, they’re fabulous. Anyone have the definitive answer on the fake/real boob thing?

  34. Grunion

    She’s no Monroe that’s for sure. Just another over hyped little girl trying to be sexy. Trying too hard I might add.

  35. lipper

    To even try to COMPARE the two, is heinous and damn right disrespectful.

    Marilyn will always be remembered, she was an icon.

    Lho… hmm who is that again? Oh yes! Firecrotch!

    Marilyn KNEW how to make love to the camera. Growl.

  36. vgcvb

    who the hell cares about freckles, if this bitch was lying down on your bed you can’t tell me you wouldn’t fuck that shit, if not you’re just straight up gay!

  37. gripper

    i swear these are soooo ugly…. i would much rather look at a rotten corpse than these.

  38. Doomhammer

    Wow, I didnt realize she was debilitated with the whore plague like she is. She looks like shit.

  39. itspat

    A little context: Bert Stern on the Marilyn shoot -

    “She hated the scar on her midriff from a recent gall-bladder operation, I told her it was beautiful. She was at a time in her life when she needed to re-invent herself, I think that’s why she accepted to pose for me, she drank gallons of Dom Pérignon, got drunk and fell asleep.”

    It’s easy to find these pictures online, including proofs of pictures Marilyn rejected for publication. She’s older and looks a little beat/wasted/sleepy. By today’s standards she’s a little overweight, lacks any muscle tone, and has smaller (natural) boobs than you’d ever think. Except for her face and especially her eyes, she looks like an ordinary chick, but the pictures are still far better than Lindsay’s.

  40. Harry Ballzack

    Her freckles are because she’s a fucking redhead you retards …. Jeezus, doesn’t anyone remember her before she turned Hollyweird ? She’s had a tit job too. She never used to have any nipples to speak of. Pointy tits

  41. request

    She looks like a worn out hyena.

  42. nipolian

    Way to go LiLo……One step closer to porn where your future projects will equal your gifts.

  43. Captain Obvious

    Looks like she is not bare down there. I guess it IS firecrotch.

  44. lidiya

    where are her hips? why the terrible wig? where’s the personality? i’ve taken more exciting pictures of dead trees.

  45. Cap'n Pickles

    I’d hit it. Freckles are a definite turn off. shit. I wouldn’t know if I was fucking Lindsay lohan, or getting a blowjob from Howdy Doody.

  46. Here’s the full set (including shots rejected by Marilyn afterwards). Compare for yourselves.

  47. stepoutsidethebox

    although lilo isnt perfect, im sure she didnt have nearly as much done as marilyn did. if u saw pictures of marilyn’s stomach pudge u’d be making fun or her too. no one’s perfect, that’s what makes us soo beautiful.

  48. 10pound

    She smells like cuttlefish.

  49. Novak

    @90 I don’t think anyone has denied that?

    Doesn’t make it any less gross. Fuck, look at the 2nd pic, it looks like she has a horrible skin disease.

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