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
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  1. SATAN

    she used to have tits right?

  2. Kim

    There is no reason that she or her sister should be getting work. Go forth and Die, talentless hag.

  3. Polk

    Ha Ha – Jessica’s wearing a fat girl cover up in all those pictures…

    She’s on a serious decline. No wonder Romo dumped here – a QB needs a girlfriend in good shape, not a fatty.

  4. The Rough report

    Great, sub-celebs are turning Fedora’s into the ugly trend of trucker hats…good i got rid of mine…

  5. SATAN

    if Jessica Simpson never had tits, would she be the most worthless human?

  6. Melissa

    The Rough report – It’s been a retarded trend for years now… Britney Dumbfuck was sporting those back when people still wanted to stick it in her.

  7. Rachel

    I think Jessica looks good.

  8. I think Jessica looks better than she was before, but Ashlee is at her best right now making Jessica look like total poop

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  9. Ascil

    Actually both looks good…but i’m better :P

  10. I got something I can shove into that open mouth of hers.

  11. jim

    Jessica is wearing a big girdle swimsuit bottom so her belly fat won’t plop out. Gross

  12. What a stupid douchebag

    Nice mouth agape “I’m surprised” dumbass pose. I fucking hate ASSHOLE simpson; she’s a no-talent dumbass & doesn’t deserve ANY work. Fuck her and her fagboy husband.

  13. Princesspink

    Wait, Jessica Simpson is fat? Wow, that’s pretty low. She has a gorgeous shape, and you people are really sounding ignorant.

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  15. Jan

    “….her increasingly thinner little sister who can actually find acting work”

    ánd a man, ánd a baby.

    Poor old Jess. Life’s a bitch.

  16. Turd Ferguson

    Fedora = Douche…period.

  17. tony romo

    who’s that midget standing next to ashlee? Oh, that’s pete. He is wee.

  18. Hank

    “Jessica Simpson is fat? Wow, that’s pretty low. She has a gorgeous shape”

    Georgeous shape if you are a football coach looking for a Middle Linebacker.

  19. Janks

    Jeezus – look at the size of Jessica’s bikini bottom. It’s like a circus tent of spandex. And the mumu she wearing to hide it all?

    The shame of fatness. Why doesn’t she just lose weight, instead of the depserate measures to hide the obesity?

  20. Yowzah! She is one stunningly hot MILF! Glad to see her doing well with Melrose Place redux.

  21. Max Planck

    Isn’t he supposed to be on a leash?

  22. yo

    you guys are fucking nuts if you think jessica is fat. and you think ashlee looks good? look at pic #8, too skinny when your ass bones stick out more than your ass. jessica>ashlee. and talking about jessicas bikini thing, she obv wore it on purpose because he cover thing is see through. i dont know what that thing ashlee is wearing is called but it looks like total shit.

  23. FACE

    what a worthless wench. There is never an excuse for lip synching on alive TV show.

  24. Tim

    Jess looks like every other fat girl at the pool trying to hide the rolls of flab. Sorry, sis, the tarp you throw over your shoulders may hide the details of the muffin top and gut, but it makes your shadow even wider.

  25. Janice Marie

    I would NOT want to stand next to Ashlee if I was Jessica.

    Jessica is a decent weight (she is NOT fat, by any means), but Ashlee’s skinniness just emphasizes her curves.

  26. a

    jessica is absolutely fucking gorgeous.

    ashlee is still doing that lurching hunch back creepy shit. i wish more people called attention to it. there was some clip too out there of her walking like a misshapen lizard.

  27. Kelley

    Holy … Ashlee is getting as bad as Paris Hilton with these dumb-assed, vapid poses … since she’s had all that surgery to cure her ugly face, she really thinks she’s something. By the way, I had never heard Jessica Simpson sing before … so I checked out YouTube to see what she sounded like. She cannot sing … at all. Not sure what Tony Romo saw in her over Carrie Underwood. Whatever.

  28. Sport

    Gross family.
    Hilarious Wentz is wearing a Zoggs shirt – nice try dude. Like you have EVER seen the sun or a surfboard. Go back to your douchey bright blue shoes, pal.

  29. Randal

    Stunning! These two need a Playboy spread. The two Simpson girls would make a killing posing together. With Ashlee’s long sexy legs and Jessica’s soft voluptuous breasts, they’d need a two page spread.

    Beautiful as always ladies!

    Randal

  30. ...

    ashlee simpson is talentless

  31. Kim

    One sister is fat pig with a man chin and a pea sized brain, and the other looks like Olive Oyl and is married to a dweeb.

    The younger sister has some nice legs to travel up, however.

  32. titsonsnack

    Is that even Ashlee Simpson? Every time I see that bitch she looks different. It could be some Australian Aborigine standing there wearing a space suit and you could tell me it was Ashlee Simpson.
    Whatever, Ashlee. You will still always be this douchebaggy Willem Dafoe-chinned beaknosed gawkier verson of a preteen pop-punk Brooke Hogan in my brain.

  33. Oliver Chester The Molester Lester

    I’d pick Jessica over Ashlee any time.

  34. Mama Pinkus

    she’s what my English grandmum would have called a “tart”

  35. dave

    @34..woman who wear less clothes then that in the uk get called a ‘tart’ or a ‘slapper’.

  36. I’m not a fan of this red/orange hair that Ashlee has been sporting. She looks much better as a blonde. And…WTF? Swimming on Saturday? It was like a high of 73 on Saturday here in Vegas. Hope that water was heated and there were heat lamps all over…lol

  37. Wait….didn’t she have a kid? How lovely that the kid’s mother is dressed as a hooker.

  38. lillie

    jessica looks stunning!! she’s showing skin but still looks classy. It was ashley’s party anyways… she shouldnt try to outdo her sister!!

    They have two different body types, jessica’s is very muscular naturally and ashlee’s is very thin – they both look gorgeous as is!

  39. lillie

    jessica looks stunning!! she’s showing skin but still looks classy. It was ashley’s party anyways… she shouldnt try to outdo her sister!!

    They have two different body types, jessica’s is very muscular naturally and ashlee’s is very thin – they both look gorgeous as is!

  40. 7L

    yeah wheres her tits.
    No but seriously shes way fucking hotter than jessica now

  41. Ashlee S Ali Lohan, losers! The plain ugly loser girls from HS who shouldn’t get any work, I agree. Ugh. What has this world come to? And that Pete Wentz hiding his receding hairline, ugh.

  42. I am really not sure about that hair colour on Ashlee. I think she would look better blonder like her sister.

  43. andediluvuan

    @ 4, it’s a trilby she’s wearing, not a fedora.

  44. Look! Look!

    that main photo is exactly the same as the one for Jon Gosselin’s Vegas Pool Party, only surprisingly less depressing

  45. Chatham

    God, would she PLEASE shut her damn pie hole! Looks like a damn blow-up doll.

  46. Sprmcandy

    Little sis has killer legs !

  47. CakeSnifferer

    Is that guy her boyfriend? He’s either really, really short or he hangs out only with tall women.

  48. CakeSnifferer

    Is that guy her boyfriend? He’s either really, really short or he hangs out only with tall women.

  49. Fucking Emo’s. I hate Emo’s.

  50. Can someone please take her off Melrose Place? She’s the only one there who can’t really act.

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