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. Onyx Blackman


  2. Blaise Bailey Finnegain III

    I’m astonished how absolutely hot she looks.

    Damn the Photoshop trickery!

  3. Duckypoo

    aven’t even seen the NSFW pics and I already need to clean my keyboard. Thanks for reminding us there is a god.

  4. Blaise Bailey Finnegain III

    Don’t fucking type FIRST, you dumb fucking faggot.

    Like anyone gives a shit that you got the first comment.

    P.S. if you care, then blow your fucking brains out.


  5. polly

    A Very ugly Marilyn wanna-be–!!! These pictures suck–

  6. zug

    Freckle Attack..

  7. UCrawford

    I don’t recall Marilyn Monroe having a tramp stamp either.

    Seriously, I’ve always thought Lohan (although obviously crazy) was still a physically attractive person. But the photographer here did an absolutely horrible job as he seems to have emphasized all her flaws (particularly the freckles, which I normally wouldn’t even notice). Seriously, isn’t this supposed to be an idealized shot and not reality?

  8. Wtf

    Oh, she is ugly as fuck.

  9. Jsan

    ….i think i just threw up in my mouth a little bit.

  10. Idk about this chick… The freckles to me are a huge turn off. Lindsey is overrated. Tatters are pretty nice though.

  11. Flavio

    I like the freckles, I want to try to lick them off. Those tits! Mmmmmm.

  12. Idk about this chick… The freckles to me are a huge turn off. Lindsey is overrated. Tatters are pretty nice though.

  13. so2315

    My God, I guess if you were drunk enough when you were fucking her maybe you could bring a sharpie and connect the dots!!!

  14. old dude (yes, looking in your daughter's bedroom window)

    Even in this carefully staged photo shoot, Lindsay has a harsh coldness that Marilyn never had.

  15. dude

    #7, you hit the nail on the head.

    But of course, I masturbated to them anyway.

  16. riiiight!

    pretty sad when you have a professional photographer, photoshop and black and white images and you STILL look like SHIT!

  17. Hill

    Wow, super ugly. At least Marylin had class.

  18. D. Richards (Chef.)

    Freckles are forever. Tits.

  19. HuckyDucky

    Hey Blaise Bailey Finnegain III,

    You must be new here.

  20. Ms. Lohan your no Marilyn Monroe, closer to Janis Joplin maybe.

  21. Jimbo’s trying to write a comment but all that comes out is “fap fap fap”.

  22. Oprah's Gorilla Butthole

    I have never masturbated before to such ugly pics.

    Obviously, I have mixed feelings about this whole thing….I should probably watch the “Parent Trap” to cleanse this funk….

  23. jakebarnes


  24. sweet honey hole

    these could’ve been way hotter. She’s hotter than this.

  25. PAULIE

    U-G-L-Y as HELL!!!!
    Freckles SUCK big TIME!

  26. Sauron

    Young Marilyn Monroe with shaggy breasts..?I’m really convinced.Even photoshop didn’t help.

  27. Mal Gusto

    Marylin was much older than Lohan during the original shoot and still her tits look better than Lohan’s!

  28. Gerald_Tarrant

    I knew it was just a matter of time before real “non-oops” pics came out.

    I love freckles on chicks.

  29. Fin Fin

    WTF?! She is hideous. Why would they ever compare the two. RETARDS!

  30. lily

    what a dirty whore plus she has no niples

  31. B.O.B.F.O.C

    Or, Body of Baywatch, Face of Crimewatch.

  32. noneyobeezwax

    if it weren’t for the tits, i’d swear these were pics of a 12 y/o boy or a sickly leopard.

  33. noneyobeezwax

    whose name is that tattood on her ass anyway?

  34. Rossco

    I’ve been waiting all this time for THOSE?
    Damn, not even jerk-worthy. Someone photoshop out the freckles, please, and then we’ll talk, haha.

  35. bobert mcnasty

    next stop….. playboy! giggity giggity goo

  36. bootlah

    And what’s with that wig? It’s horrible.

  37. monkeyfightclub

    Her face looks like Marilyn Monroe’s exhumed corpse. It’s like they went out of their way to make her look like crap. Her body looks great though.

  38. TetraShiva

    Wow. That is really…. not hot.

  39. The Office Whore

    I have absolutely nothing to say..

  40. amma

    I’m afraid the photog was aiming too high–Lohan ain’t Marilyn. Marilyn had a curvy, tiny little waist. Lohan doesn’t appear to even have a waist based on these photos. But the funny thing–Monroe was in her mid-thirties when the original photoshoot took place, and ya’ know what? Lohan looks the same in the face, got THAT part right…Great boobs, but totally unoriginal. And she’s not good looking enough to pull it off. Sorry.


    There was also no avoiding the parallels between Monroe’s tragic fate – dead from an accidental overdose of prescription medicines – and that, recently, of Heath Ledger’s.

    “They are both prime examples of what this industry can do to someone,” says Lohan.

    When it is pointed out to Lohan, who has been in rehab three times, that the possibility may exist of a similar fate for her, the young actress replies with a tinge of annoyance: “I don’t know. I’m not them. But I sure as hell wouldn’t let it happen to me.”



  43. LINDSAY IS geez i don't care, man

    #41, chill out, they’re only here for our dying-Roman-civilization entertainment…

    But that picture in black-and-white with the yellow flowers (or whatever they are) – that’s not Marilyn as much as Jame Gumb preening in front of his mirror after tucking it back.

  44. Luisinho


  45. El Ces

    Okay…I luv boobs, I just don’t undestand what this photoshoot was for?
    What was New York mag selling?
    Were they just like “Well, here’s Lindsay Lohan naked, enjoy.”

    Was it for a car or…why?

  46. Edwin

    No, Janis was much more attractive, even stoned.

  47. Lowlands

    Putting on a blond wig doesn’t mean that you’re Marilyn monroe right away.But these are very comic pics,almost cute??She looks more Paris Hilton to me.

  48. ella

    national geographic boobs

  49. Nics

    ew the black and white photos look like they used one of those lights that show you how much skin damage you have

  50. mike

    #39 – why should today be any different?

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