Jessica and Ashlee Simpson at MTV Australia Video Music Awards

April 12th, 2006 // 150 Comments

When did Ashlee Simpson start looking so much better than her older sister Jessica? And more importantly, when did Jessica Simpson transform into a stubby mole creature with no neck? I’m pretty sure I used to think she was attractive, but now I just want to feed her carrots through some cage bars.



  1. rmeno

    It’s the curse of being the “older” sister…it catches up with you one day.

  2. DonLes91

    First! Good Lord, she’s anorexic!

  3. KatieA978

    Ugh – as an Australian, who had to put up with traffic chaos cause of the show last night, please take them home again.

    On side note, there was a lovely photo of Jessica and her father in one of the papers, and she was looking very summery, and he was looking at her tits.

  4. DonLes91


  5. Equalparts

    Ashlee was always hotter than Jessica. Ain’t sayin’ much, though. Jessica looks like her face was pieced together with sculpy clay. And what’s up with her tongue always sticking out through her teeth when she smiles? She’s just so cutsie-wootsie that I wanna kick her lower jaw up through her eye sockets with my steel-toe boots. While wearing Princy jeans.

  6. It’s not easy to age gracefully…

    #3 – her father was checking his own daughter out? Shee… what’s with that family.

    I think all these celebs would look better if they stopped wearing the zombie makeup, ie. dark shadows around the eyes.

  7. Italian Stallion

    How in the hell did Nick get her neck in the divorce?
    I heard of someone going broke from a divorce but that shit is crazy…..
    What the hell is Joe Simpson gonna choke while he fucks her….

  8. suzy

    they switched hairdo’s lol

  9. Feed_Me_Chocolate

    The whole look of her peering at the camera behind her hair, wearing a drugged grin is better suited to a strait jacket.

  10. mamacita

    And sibling rivalry rears its ugly head again. Wait, no, that’s Jessica’s head. Whatever. I hate her hair.

  11. amajean040904

    what the hell,I’m confused sence when is ashlee hot for that matter sence when is ashlee a women i alwase thought she was half pre-pubescent boy and half Scottish terrier.
    hum who knew.

  12. scarlett138

    lol yea i think its the hair & that ugly dress…jessi’s still much hotter than her fugly sister though, guess thats just a lucky pic for her.

  13. I love K-fed's Corn Rolls

    Same thing happened to Britney… Jamie Lynn is better looking too!

    Ahhh… it sucks being the “pretty” one and then the ugly fat loser… although I do enjoy watching them both plummet from the sky.

  14. Trotter

    #3 – I’m with you. Her dad used to pimp her to the “Christian Labels” and when even they got sick of his ogling and lapping, he went “mainstream” with his little dream girl.

    That man has the hots for Jess, and now Ashlee has finally figured a way to get more of Daddy’s attention. Anorexia. Look! Its working!

  15. I don’t understand why the general population doesn’t get it blonde and tan does not automatically equal pretty! (or even that someone used to be pretty), here’s proof for everyone! Oh, and if you’re blonde and tan and think you are really pretty you should probably try to get a modeling contract that isn’t “adult,” rethink it, you know?

  16. shell

    Daddy Joe would hit that…again…and again…and again.

  17. It’s like choosing between a groin pull and an ACL tear. What’s the difference?

  18. Star Maker Machinery

    Did Asslee get a nose job? She still looks like a pre-op tranny.

  19. krisdylee

    I have to go tell Grandma I found her curtains.

  20. Good lord! Jessica looks like Hillary Swank! And that’s not a good thing. It looks like Ashlee is on the fast track for sluthood with her Paris-ian look.

  21. Grphdesi23

    Ashlee and her retarded sister, Jessica.

    Jessica says “”They say I have a mentality of a kid, but I don’t know what that means.”

    She then drools all over herself and asks Ashlee for some pop rocks.

  22. #16, I think daddy Joe has already hit it, again, and again and again…

  23. Grphdesi23

    By the way, I heart retards.

  24. ESQ

    Either Jessica just got caught in a wind tunnel OR Ashlee caught her having sex and interrupted her for this photo op.

  25. BabyBayBayLeigh010

    If you look at a close up photo of Jessica Simpson, right above her upper lip is this very grostesque and disturbing wrinkle…check it out…you won’t be disappointed!!!

  26. Doc

    pic is definitely doctored btw… i doubt that it a real pic of the simpson sisters…

  27. ESQ

    To add to my last comment:

    As she was getting caught doin’ the nasty she accidentally threw on the hotel curtains thinking it was her dress. Sex will make you do crazy things will it not?

  28. Kfir

    Ashlee is holding a figure of what appears to be a duck or platypus.

    Blonde pop singers = comedy. (though Ashlee was previously dyed black. Maybe she wanted to become more funny?)

  29. guys, we are all missing the point here. ashlee simpson won a music award. a music award for her MUSIC. wow.

    anywho, i agree with #26. the picture looks doctered to me as well.

  30. Jewbacca

    Ive never looked at Jessica’s face before, she usually has those mammoth mammaries hanging out. Ashley still is a dog.

  31. dee

    I think that Jessica probably toned down her looks for Ashley. I mean, does she ALWAYS have to be the hotter older sister? I think she’s just giving Ashley a break. Look at the picture, Jessica’s barely wearing any make-up, and she’s wearing a damned sundress!

  32. LRonHoover

    I WOULD HIT THEM BOTH. period.

  33. I’ve seen this phenomenon somewhere else……oh yeah, that idiotic movie Face/Off. It has become reality.

  34. Wow. Ashlee does look nice.

  35. alreadyproud

    I’ve been reading the superficial for decades and I’ve never laughed this loud at a Jessica Simpson joke. I’ve got to put my blackberry away. The other people at the funeral are looking at me weird.

  36. CancerNipples

    This is pretty stupid. Jessica doesn’t even look bad in that picture!

    She looks BETTER than usual, better than when she’s rocking a cheeto tan and and has her face painted like a clown, and teeth bleached brighter than the sun.

    And I’ve always thought Ashlee was hotter. Jessica is too stumpy.

  37. KatieA978

    #26 & #29 – not doctored, that’s what the lovely Simpson sisters looked like last night at the Australian MTV Music Video awards. Hate to tell you but they do look THAT BAD. Why would you photoshop, when the real deal is bad enough?

    Which reminds me – an Australian guy won “Best Male Artist” over Robbie Williams, Kanye West and others. He’s sh*thouse and the runner up of Australian Idol. Ashlee Simpson won Best Female Artist and another award too… Notice the calibre of the event??

  38. tuben

    # 18

    FUNNIEST LINE EVER!!!! (can’t breathe from laughing)

  39. Anonymous

    Ashley could win ANY ugly contest. I think she is, hands down, one of the ugliest wannabe celebrities.

    Jessica actually looks decent in this picture, although she looks more plump than usual. I like her this way, with minimal make-up. Normally, she has so much junk on her face, she looks like a transvestite whore.

  40. I don’t know why us Australians insist on humiliating ourselves time and time again. First our Prime Minister gives George W. a heady, then Ashlee Simpson gets chosen to host the Australian MTV VMAs. Yes you heard right, she was the host. The highlight was when she said something along the lines of, “I love going down under”… She’s morphing into Paris Hilton! Her parents were back stage! That’s like telling your Grandparents about your farm animal hitting fetish (don’t judge, we all know how donkeys are hung)…

  41. RougeRed

    Ashlee’s probably wearing mega heels, and Jessica maybe (just maybe, people) is still having a hard time over her divorce?

    I think it’s nice that Jessica doesn’t look overly polished for once, but I do think Ashlee needs to be reintroduced to food.

  42. Ashley Simpson won best female artist for what achievements? The art of silent lip synching?

    Australia seems like a funny country!

  43. colormeskanky

    Is it just me or is Ashlee starting to look more and more like Paris Hilton? That’s not a good thing, by the way.

  44. KatieA978

    Sally – (#40) it’s because the Aussie choices that are at all known overseas, and hence getting the “press” they wanted, were Russell Crowe or Ben Lee (the artist formerly known as rooting Claire Danes and who sings the biggest load of shite I’ve ever heard).

    Considering the options, I though an overseas artist was better – although the Simpson sisters do not artistes make.

    Skanky hoes – yes, artistic talent – no.

    I would have preferred Snoop Dogg, he was here for it, and at least we could have seen some swearing and lots of naked people.

  45. Juliana's love

    Jessica, Farrah Fawcett called, she wants her hairstyle back

  46. RobotAttack

    well…… Jessica just took an exceptionally bad picture at the same moment that ashlee happened to take an exceptionallygood one. it happens.

  47. Katie – You’re right… We could have had Shannon Noll, though…. Yup, 2 hours of nasal would have been peachy keen… I woulda loved Snoop Dog hosting… Hahahahaha, he can Shasizzle our MTVizzle awards any time. God that sounded too little cool and too much Mark Holden…

  48. I still think Howard and Bush make a cute couple, though…

  49. Pez_D_Spencer

    Interesting ‘do on Jessica. What was she going for? The anime robot-pilot look? Shouldn’t it be a little spikier on top, then (and green)?

  50. Trotter

    KatieA978 – your posts make me want to kill kittens. For the love of kittens shut the fuck up!

    You have NEVER written a funny syllable.


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