Caption It! #29

July 8th, 2005 // 40 Comments
By Miu von Furstenberg

  1. Jodi

    NO!!! Not the chains again! I promise not to lip sync next time!!!!

  2. kathyp

    Ashlee prepares for her next appearance at the annual Southern Baptists Convention.

  3. yikes

    OH MY GOD! That’s Ashley Simpson! I thought that was Christina Aguilera!

  4. Jen

    Poor girl can’t even look sexy in lingerie. How sad.

  5. Suzanne

    Hillary Duff and Joe Simpson pimp their bitches.

  6. *vomits*

    Her face looks digusting all droopy like a 50 year old.

  7. harriet potter

    Justin Timberlake and Christina Aguilera on the cover of their soon-to-be-released porn movie that someone “stole” from their super secret locked safe that no one knows about.

  8. “Bitch you got AIDS.”

  9. olivia

    Ahhhhhhh the joys of photoshop.

  10. countbranca

    God, she is hideous.

  11. *Micha*

    Boy George debuts his new S & M themed video just weeks after joining the Hair Klub for men.

  12. The only way Ashley Simpson can ever get and keep a boyfriend is if she physically keeps him in chains.

  13. Jean Jeannie

    This looks photoshopped! People… look at the proportion of her head to the rest of her body.
    Plus the body looks too lean to be Ashlee’s. She’s
    a lot chunkier and less toned!

  14. Ok.

    I put on the chains – JUST LIKE YOU ASKED.
    I am acting str8 – JUST LIKE YOU ASKED.
    But if you think I’m gonna lick your armpits for a frickin’ second – YOU GOT ANOTHER THING COMING SISTER GIRLFRIEND.

  15. Steve

    That’s AMAZING! That’s right from the recurring dream that I have about beating her to death with heavy bits of chain.

  16. A Boy and His Dog

    2 words – W H I T E T R A S H !

  17. Hailey

    That’s not Ashlee Simpson~~ This girl just looks like her!

  18. /-\ALEXANDER/-\

    Nappy hair + No ass= not impressive. I don’t criticize too much, but what a tween-looking thing she is. She needs a milkshake.

  19. manhattan

    yeah, it’s
    disgusting + pointless + desperate=why does she even try?

    Is that the bassist from her band she’s been paying to hang out with her?

    I wonder who’s idea this was over @ her record company. They should be fired for making her look dumber than she already makes herself look. Somebody needs to get her a real publicist.

  20. medea

    The New pussycat doll,

    ASH(LAY) Lypsyncson

  21. yvette

    she looks rediculous and that guy idk but he kinda looks like benji madden but i could be mistaken does anyone know who the guy is?

  22. c

    daddy simpson’s little girl.

  23. fizzy

    it was probably her dad’s idea!

  24. Jess

    My daddy has decided to hook me too.

  25. IMesh

    Hailey is right–it’s definitely just a look-a-like! At first glance it does look like Ashley but if you look for a couple more seconds you can tell it is not her.

  26. Callie

    Shes in Porn already? :P

  27. maryjane

    Whether this pic was photoshopped or not, that’s DEFINITELY Ashlee Simpson’s face, and she is still FUGLY!!!

    Gawd! I hate ugly ppl who become famous because they are riding on a sibling’s fame! She SUCKS!

  28. Spaz Cadet

    What a good little Baptist Christian Ashlee is! Yeah, it’s totally photoshopped, but these days that doesn’t mean she didn’t pose for it.

  29. Katie

    I thought that was Paris for a second, but she’s skankier.

    What is Ashlee doing dressed like that? I thought she was going for the Jessica look now.

  30. lizzielou742

    She’s a MAN, baby!!

  31. ashley

    In an attempt to recover her ill-fated career, Ashlee Simpson has made a cross-over into the world of S & M. When asked if this conflicted with her strict Baptist upbringing, Simpson responded: “Oh, I’m not actually having sex. I’m just pretending… kind of like when I pretend to sing!”

  32. Trisha

    Jessica, Jessica, Jessica…screw her and Her daisy dukes. I’m so hot

  33. that aint ashlees bod. she wishes!

  34. mia

    I thought that guy was the singer from Good Charlotte… but I figure he’s a little too buff.

  35. stephib82

    That’s not Christina Aguilera? What the hell happened to Ashlee Simpson? I think someone needs to fire her handlers (daddy).

  36. Stax

    Definately not benji from Good Charlotte, he has no tatts.
    She’s just horrible yeah!!

  37. lala

    wow, this is getting so desparate, from the “hoe-down” to the “cant keep a good hoe down.”

  38. Joz

    Thats not Ashley. Shes not that hot, nor has she had her hair that way before.

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