Ashlee Simpson @ CosmoGIRL! Born to Lead Awards

whoa she's looking good ...

I'd fuck the plastic right off of her.

Indeed. She doesn't look half bad....

Way hotter than her sister. I bet I'd shoot my load in 30 seconds with Ashlee, but the slightly less attractive Jessica would take me atleast 2 minutes. Either way, they would look like somebody lathered them up for a face shave when I finished.

Looks like an Olsen twin.. plastic surgeon went too far

She's looking better and better while her sister is slowly morphing into an ugly tranny.

she looks amazingly good here.

Wow. She looks good. Really good.

She also needs to quit getting work done. Daddy should make her stay away from the cosmetic surgeon. If she doesn't stop now she's on a slippery slope to Jenna Jamesonland.

Yeah, she does look like an Olson now....and she's got Paris' lazy eye in the pic on pg. 2

if she had jessica's tits she'd be perfect

a chick with millions, decent body, and daddy issues. sign me up. i'd fuck the living shit out of this bitch.

Bitch can't dress and her nose job is melting off of her face.

Here's the problem. if a girl, who looks like that and ISN'T Ashley Simpson, came up to me and whisper'd, "lets go fuck!" - well, i'd be gluing that girl's eye shit after i pounded the living daylights outta her puss.

seriously. glued shut. if it WASN'T ashley simpson. but because it is... i can not. and will not.

the other woman is not lauren baccal and i think ashlee looks beautiful here.the only reason why you all say no it's because she is ashlee simpson.

I'm guessing that the old broad is Helen Gurley Brown, the longtime editor of Cosmopolitan magazine.

Amazingly beautiful. I wish she would show off her gorgeous body though.

Damn, Ashlee is fucking gorgeous.

I don't care if it is all from plastic surgery or not, bitch looks really hot.

Her sister's body still ranks as top 5 when she is in shape but I think Ash has her beat in the mug department.

That Pete Wentz dude seems to be quite the douche but I'm no hater, he is doing something right.

YR is correct
it is Helen Gurley Brown
whoever the fuck that is
anyway lauren bacall is still on of the hottest women ever

That elderly lady has one of the biggest heads I've ever seen.

She's not ugly, but her face is so average. I mean there's nothing that really stands out...this is why a flaw is a good thing...no flaw makes for an extremely forgettable and boring mug....she just lost all her personality under the knife.

She looks very pretty. But, she better since she spent several thousand dollars. I agree with most of y'all on that she's getting beautiful while Jess is turning tranny.

All that surgery and she is still a fugly talentless idiot, I see the bum chin had work done on it, fuck off Ashlee and take your thick as shit sister and pervy Dad with you.

You bring shame to the Simpsons name.

yesssss, the best here is: HELEN GURLEY BROWN. SHE IS GREAT !!!!!!!

MuCH Cuter than her sister

man, that woman seems to be rotting...how old is she? like 100+ something?

i'd hop on gurley brown...less plastic and more meat...tenderized with age...i bet that lower intestine feels like gravy...

she looks hot. she looks alot better. however jessica is still the hotter...

That caption is hilarious, cuz it really does look like she's pulling away from the old lady.

Anyway, Ashlee is hot but she's wasting her hot years on Pete Wentz. She is so gonna regret that one day when she wakes up 10 years from now.

To me she always looks the same and I have a hard time looking into the face of someone with a wonky eye.

she doesnt make me want to La La.

the 'get this bitch off me' is pointing to the wrong person. the surgery looks great but i can't handle her

No.

Too bad she didn't get her sisters "rack".... she'd be a "MAJOR" hottie then

dude that "bitch" is Lauren Bacall
one of the hottest women of all time