Jessica and Ashlee Simpson are matching clowns

January 19th, 2007 // 54 Comments

Jessica and Ashlee Simpson were spotted leaving Koi together wearing matching red lipstick on their face. Although to stand out, Jessica thought she’d attend dinner looking like a tranny. Mission status? Accomplished.

Thanks to the oddly named Jelly for the tip.



  1. Danner


    Street whores!

  2. BarbadoSlim

    So papa joe had a nice freaky three way then.

  3. ~!@#$%^&*

    “Jessica, point to your penis, sweetie!”

  4. NipsyHustle

    hooker dee and hooker dumb. you figure it out.

  5. magickal


    I hate these two. Although, Ashless looks much, much prettier after all the plastic surgery. But nothing can fix the look of pathetic washed up failure on Jess.

  6. misanthrope

    Joe Simpson must be using red lipstick on his dick.

  7. magickal

    Woops ~ AshLEE not AshLESS. Although, ASSless would have been appropriate.

  8. anothershityear

    this looks like a contest:
    how much untalented disappointing failure can possibly be crammed into a single photo?
    (answer: with these two alone, a hell of a lot)

    the chick in the background looked better than either of these two in her day, and by the looks of it didn’t need a plastic nose to do it

    and btw, jess. simpson is around 5’1″ right?
    and she’s towering over the dee-clown (thx #4 hilarious!) in this pic
    how (non-) tall is a. simpson?? 4’7″????

  9. I had a 3some with them and now both of my balls are bright red!!! Hey-oh!!! Unfunny joke!!!!

  10. anothershityear

    j. simps. looks like freddy mercury in a blonde wig in this pic
    (sorry freddy — no offense)

    #2 & #6 good ones, always up for creepy-ass joe-s humor

    ok enough bullshitting around, back to my shit-job now

  11. MissLaVey

    Who the hell still wears red lipstick, anyway? I always thought it looked like hell on 99% of people.

  12. danielle

    They’ve got to be the fugliest pair of sister’s on the market to date. No, wait. The Olsen Smurf’s top that list…then the Simpsons. Or maybe it’s the Olsen’s, Hilton’s and then the Simpson’s.


    Just throw a wet brick at each of ‘em to even the playing field.

  13. Pointandlaugh

    oooooooo how F-ing HOT would it be to get a 3-some with those whores? Seriously. Holy shit. I would tap those asses with the finesse of Ike Turner.

  14. wedgeone

    “Jess? Jess is dead, my friend. You can call me Joker and as you can see I’m a lot happier.”

    One more thing: “this world needs an enema” starting with these two.

  15. Jacquelantern

    Ashlee is way hotter than Jessica.

  16. ming

    wait…isn’t that marilyn manson and his new girlfriend?

  17. jrzmommy

    I’ve been unable to comment because I keep falling asleep when I look at this thread.

  18. cruzin333

    American Idol recently held auditions in Seattle with a woman who strikingly resembled these two Simpsons, with the fire hydrant red lipstick and a “sexy” look, the whole deal.

    She sang “Don’t Cha” (wish your girlfriend was hot like me…) and I bet she was even as good a singer as these girls. *(sarcasm)*

    Shocking, I know.

  19. GeannaSparrow

    Haaaa. Jessica looks like a damn flasher.

  20. 86


  21. Mo

    Somebody’s been playing in Cameron Diaz’ closets again.

  22. google

    Ok, something more entertaining – this may be the greatest illegal performance-enhancing drug story ever in the history of sports:

    “AC Milan striker Marco Boriello tested positive for cortisone after his side was beaten 2-1 by Roma last November… But he blamed his girlfriend, Argentine model Belen Rodriguez, 22, for his positive result in the test due to a cream she used to cure a vaginal infection – which he unwittingly “ingested” whilst paying attention to the aforementioned part of her rather delectable anatomy. Though it probably wasn’t that delectable at the time, hence the cream. A cunning excuse for sure.”

  23. 86

    I wouldn’t stand right next to Ashlee if I was Jessica.

  24. BarbadoSlim

    @22…He’s using the “my girlfriend’s twat” defense. How considerate of him, and classy.

  25. I wonder if one put the lipstick on, they made out, then it was on both of them…

  26. jrzmommy

    “My Girlfriend’s Taco Has Too Much Cheese: A Step-by-Step Guide to Self-Ruination of Every Man’s Dream of Fucking a Super Model”……by Marco Boriello

  27. jesseeca

    jessica looks possesed, ashley looks like she’s on something & they both look like jessica’s dog. run a comb through that mess! or maybe they’re both wearing one of jessica’s wigs.

  28. biatcho

    #22 That was excellent. Just another fucking cheating Italian Footballer.

    They should be banned from Champions League play I say!

  29. misanthrope

    @22… His gal’s fun time area must be pretty alluring if he went on ahead and visited it with vaginal cream and all. And quite passive-aggressive on her part…. ‘Should I tell him or should I let the asshole eat yeast cream?’

  30. ch474

    Time for a visit from Miss Cairol for these two.

  31. cole007

    oh god, they want to be the olsen twins so bad they can hardly stand it!

  32. Holy shit… Ashlee looks nothing like she used to. That is scary.

  33. wedgeone

    @22 – Thanks for making the thread attached to this useless article worth rereading. Anyone want to take bets on when Beckham pulls this excuse out when he starts his soccer career in the US?

    I say before the end of the 2007 season, we all find learn that Posh’s snatch is mean & green.

  34. wedgeone

    “finally learn”, not find learn.

  35. Just throw me in between them with some Jello.

  36. BarbadoSlim

    This is very difficult for me but, this is how I feel about Victoria Beckham: I’d rather risk my life hitting Paris’ fetid rathole than hit that sour Highlander cunt.


  37. HollyJ

    Anyone who thinks they’re opposed to cosmetic surgery needs to seriously reconsider after seeing these two next to each other BEFORE and AFTER. Ashlee’s gorgeous now. I glad she cut off her beak. But I hate both of their chin butts.

  38. jraleigh

    Does anyone else notice that it looks like Jessica is trying to masturbate through her coat?

  39. spunkbubble on J.alba's face

    who’da thunk that Ashlee would be hotter with her sister? She was only one nose job away this entire time.

  40. Butterfly

    Why didn’t someone tell these two to blot their lips. It looks like they’re wearing those wax lips!

  41. bootrungar

    the next Barbi twins have arrived

  42. Dejasade


  43. dystopia

    With that sneer, Jessica looks like the Joker. Only uglier.

  44. shofaz

    Jessica is so f*ckin’ ugly!!! OMG botox is eating her face… gross!!!

    Ashlee is the perfect example of how a plastic surgery can be something good for ugly people. Sometimes. She looks beautiful. Only that poor Jess is completely the opposite. Bad surgery happens, you know… look at her!!!

  45. you_betcha_iris

    26: that was rotten dot com :) LOVES IT

  46. pookiedoo

    Jess looks like she’s trying to surreptitiously adjust her maxipad. Maybe that’s NOT lipstick on their lips.

    I must vomit now.

  47. allgravybaby

    enough said

  48. Nikky Raney

    ashlee looks so different since her surgery

  49. wedgeone

    #45 – Que’?

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