Madonna nude painting is… I don’t even know

May 28th, 2009 // 62 Comments

Here’s a nude portrait of Madonna and Guy Ritchie painted in 2005 that goes up for auction on Saturday in Scotland. I’m going to go out on a limb here and assume the artist is blind, so no one had the heart to tell him: A.) He was supposed to paint Madonna not Britney Spears. And B.) Guy Ritchie isn’t a 1920s caricature of a black man trying to steal “the white womens.” Stop me if I’m getting warm.

NOTE: Pic links to NSFW version, so don’t get fired looking at cartoon nips.


  1. KVF

    Uglyest painting ever. Sure it´s not Madonna ? Doesn´t she look like that in the morning ?

  2. whatever

    Is it just me, or does the “woman” in the painting actually look exactly like Sarah Jessica Parker?

  3. sherry

    Wow. I’d have thought it was supposed to be something about cave people titled “The Dawn of Man.” I would bet two things: 1) Madonna hated it. And 2) Ritchie is auctioning it off publicly just to piss her off. Both work for me.

  4. CakeSnifferer

    It’s actually a rather flattering likeness of her.

  5. rq

    bahahahaha. #2, YES.

  6. Tim

    Why did they pose it with Guy Ritchie lying down?

  7. pete

    That’s exactly how Dee Snider of Twisted Sister would look now, if he straightened his hair.

  8. smarter.than.all.of.youse

    The tall building in the background is a metaphor for Madonna’s penis. I am an Art Major, so I know this stuff.

  9. Io

    I don’t know fish, seems to me that painting of madonna is casting her in a very beautiful light

  10. Matt

    Too bad the artist didn’t have the courage to paint her erection.

  11. Erica

    LOL #2. Yes, yes she does. An apt superfish description too. Hats off.

  12. I suppose the stars are for comedic relief?

  13. Dar

    I’d like to congratulate the artist–I never thought anyone could paint anything uglier than a LeRoy Neiman painting. I freely admit I was wrong.

  14. havoc

    Too much meat on her to be Madonna..


  15. havoc

    Too much meat on her to be Madonna..


  16. That’s Bullet Tooth Tony in a painting with a female likeness of Woody Allen…

  17. Michaela

    @2: She DOES look like Sarah Jessica Parker! Before I read the headline I thought it was a painting of her. Maybe that man is not Guy Richie but just some random New York construction worker!

  18. Joe Fonebone

    Why are we always told there’s a NSFW version and there never is? I’m never getting fired at this rate.

  19. sweet cheeks (HIV+)

    I think she looks just magnifico here! I have all her albums and me and the girls (with cocks) still dance into the wee hours of the night to her rhythms (I have a hard time these days with me illness).
    Go Lady M!!!

    Kisses (Hershey’s of course darlings)

  20. Fuzzy Tingle Times

    Guy sort of looks like a tan version of sloth.

  21. jaysus

    looks like Streisand

  22. Dubya

    As a Scot all I can say is……..WTF!!!!!!!

  23. what?

    A trifecta! Now, not only can’t she act & sing, she can’t paint either! Why oh why can’t this washed up twat just GO AWAY already???

  24. Deacon Jones

    That reminds of the women I brought home from Seacrets in OC,MD.
    Not only couldnt I get a hard-on, it actually retracted, like a turtle’s head

  25. Sport

    Sadly the scary painting looks 1000% times better than the scary real thing.

  26. FuzzyBean

    Where’s Guy’s dick?

  27. huh?

    UGH….looks like Donatella Versace.

  28. Andy


  29. justifiable

    #23 You missed the artist’s signature in the corner. The portrait’s OF her, not BY her. And she can’t act for shit, that’s true.

  30. mikeock

    I hope she didn’t pay money for this. It looks like they painted Tara Reid’s right tit instead.

  31. Jibbly Biggins

    I said zombie, you stupid painter – not cave troll!

  32. Beeotch

    Looks like Fabio with breasts

  33. Feebee

    It’s by a Scottish artist Peter Howson, who is fucking brilliant.

  34. MaryJane

    Tutuly Sarah Jessica Parker or Donatella Versace-two good answers. I knew going into the comments they would say shit like “What? This is a perfect artist rendering!”
    so funny-
    but really man this is one shitty ass artist….. he’s like “Presto! Your wedding portrait is done!” the bride just starts bawling and punching the groom.

  35. The Detroit-Ho Cryptkeeper

    Nah, looks too good to be Madonnkey.

  36. Matt is a riot

    #10- I spit out my drink on that ! The absolute best!

  37. PunkA

    Madonna has a small cock. But, lucky for her, she is still thin and flexible enough to suck it. Plus, her boys love it when she pokes them in the ass with it.

  38. Alli Watermelon

    #2 yes, it does resemble Sarah Jessica Parker! Hahaha, genius! And..when did Madonna get boobs?

  39. Amanda

    It’s actually a painting depicting the night that Andre the Giant was conceived.

  40. Gando

    This is the style of the artist.Artists have their ‘signature.’

  41. Galtacticus

    To tell you all honestly.The first time when i arrived in the West,i saw all the people like this artist does.I recognize his style.

  42. Voila!

    The artist definitely captured her muscular man arms… If it wasn’t for that, my first thought would have been Linda Hogan.

  43. Rhialto

    @41 That’s why he’s making his Neanderthal jokes! Something from the past. . .

  44. Darth

    At least her belly button looks Asian!

  45. Galtacticus

    After several succesful surgeries i’ve become finally a caucasian myself!

  46. Nero

    #45 I hope you didn’t have the same surgeon who did Michael Jackson?

  47. Rubbish! Madonna has never looked that good.

  48. Gems

    Wahey! my landlord actually has another painting by the same artist hanging in our house right now! lol

  49. Gogee

    I’d recognize Mike Tyson anywhere, but who’s the guy behind Mike with the big hand?

  50. Madge is seeing herself like this?

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