Ashlee Simpson’s Vegas Pool Party

October 5th, 2009 // 82 Comments

Ashlee Simpson celebrated her 25th birthday at Wet Republic on Saturday with Pete Wentz and Jessica Simpson in tow. Personally, I’m surprised these pics don’t include Jessica palming the entire cake into her mouth after spending an entire day with her increasingly thinner little sister who can actually find acting work. That’s a depression sandwich smothered in loneliness gravy. Great, now I’m even talking like her.

Photos: Getty, Splash News

  1. cc

    How the fuck did these two no-talent, brain idiots manage to become famous? There are 300 million people in the US…this is the best we can do?

  2. Seriously, Ashlee can (in no way) hold a candle to Jessica. Jessica is drop dead gorgeous! Ashlee is very pretty, but she’s losing too much weight.

  3. Fat Chicks Suck

    @53: You’re kidding, right? Jessica is a disgusting chunky mess and looks terrible. Ashlee popped out a kid, lost the baby weight, and looks pretty damn good. Those are some hot legs. She doesn’t have the huge tits like her sister but huge tits are overrated. The chicks with tight bodies are the ones that look good naked and that’s what really counts. Jessica is DISGUSTING and Ashlee is actually pretty hot. Nobody in their right mind would think the reverse.

  4. B.

    You guys. The bikini Jessica is wearing is called fashion nowadays. I don’t know where you’ve all been living… Under a rock maybe??
    And in my opinion Jessica looks better than Ashley at Ashley’s party. I hate waht she’s wearing with the whole hat and playsuit thing going on.

  5. Mr.Q

    You gotta give it to her, she really does look pretty.

  6. el ces

    Mmm, cupcakes.

  7. bob

    @Fat Chicks Suck

    spot the virgin. i.e. YOU!!

  8. bubba

    Great chin Ashlee is sporting there? Is it the Bruce Willis designer model?

  9. gotmilk?

    43, no one cares what it’s called. one still looks like a douche wearing it.

    this bitch better have eaten at least 4 of those cupcakes. the ribs sticking out of that outfit is terrible.

  10. Hello There


  11. Darth

    Since it’s her Vegas birthday pool party.The audience should have thrown her in the water.

  12. See Alice

    Who is the dorky guy wearing the dorky hat ?

  13. kat

    Yikes! She looks like Phoebe Price!

  14. kat

    Yikes! She looks like Phoebe Price!

  15. Leah

    Ashlee is curve-less and looks like a boy…what is the appeal?

  16. TaylorT

    I’m sorry, but Ashley is downright PLAIN and that’s why she doesn’t eat. Being stick thin makes her feel superior to beautiful women (Like big sis) with curves because our society worships youth and women who look like children (which is just sick IMO)

  17. Vinny

    Ashley’s face looks plastic-fantastic, sure, but she has no butt, no boobs and no womanly curves to speak of compared to her much sexier sister. Why does society worship stick thin girls…it’s stupid.

  18. Sapphire

    She’s beautiful. Why would she have to have huge giant tits and big fat ass to have a beautiful shape? That’s only for horny men sitting behind their computer who dream about porking women up the ass. She’s hot and she can rock any outfit, great legs!

  19. Jonovan

    Ashlee Simpson has the sexy feet. Wow!

  20. I still can’t believe how beautiful she looks after that nosejob…

  21. Pic 9
    Ashlee: “I’m with stupid.”

  22. I thought pic 8 looked fucked up. The other side of the story:

    Why does Ashlee wear such fugly clothes?

  23. AMO

    Ashlee’s a loser and why can’t Jessica be seen in her swimsuit w/o that strange old lady cover up?

  24. Liv

    Ashlee looks like she’s on meth or something.

  25. anonimous


  26. This is a cute picture, i cant remember ashley’s former face lol…..

  27. Whne is she doing SNL again?

  28. Licia
    Commented on this photo:

    Hey Kim I think ur so beautiful believe it or not I just started watching ur show!!! People are telling me I’m so late dat was last season….. I said dat to say I can’t wait for da new season to start!

  29. maddie picard
    Commented on this photo:

    you are my role model! i would love to meet you one day. i want to be just like you when im older! nd i love the Kardashian Konfidential book:)

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