Jessica Simpson has giant saggy knockers

January 24th, 2007 // 100 Comments

Jessica Simpson was spotted leaving Nobu with John Mayer sporting some very impressive side boob. And I’ve concluded the only angle she doesn’t look completely awful from is either topless or almost topless. Or falling down the stairs because she forgot how to walk. She’s lucky she has a nice rack, otherwise instead of getting felt up by guys she’d be spending her Saturday nights trying to figure out why her microwave isn’t heating up her frozen dinners. Here’s a hint, Jessica, that’s your washing machine.

And to make this remotely newsworthy, Jessica Simpson has joined John Mayer on his tour bus in Florida. Whee.


  1. ScottInFlorida

    Maybe I have a chance now?

    Sadly the answer must be no.

  2. Nooken

    That dude has huge knockers…

    Is she falling in the last picture or doing a sex doll impersonation?


  3. PrettyBaby

    No,No Guys, she is still cute I think. I still think she is way cuter than a lot of the bag o’bones celebrity cunts. Besides, I am partial to big tits, having the giant rack that I do ;)

  4. PrettyBaby

    But John Mayer- wtf chic?! Bam Margera was better than that even though he was married and gangbanged her with all his buddies- he still is hotter!!

  5. PrettyBaby

    I gotta just bitch for 1 second more- John Mayer is such a fucking downgrade…

    Think of Nick Lachey for a sec… pretty nice huh? Then glance at these pics of Quasimoto and then yell gaaaaaaahhhh!

  6. DrBob2607

    Wow.. Talk about mixed emotions – on one hand, I’d like to spackle her face with the ole Black & Decker wiener trowel, and on the other hand I’m freaked about those grandma titties hanging out the side of what ever it is she is wearing (I think it is the flag of some obscure African country).
    BTW – Is her dad still taking all her photos?? Ewwww…

  7. schack

    she’s lucky anyone will put up with her company. no one really deserves to be loved. some people recognize that, and try to be more lovable. for jessica, she walks around like it’s her god given right.

    why? she can’t sing, can’t dance, can’t talk, can’t walk. all she does is annoy, annoy, annoy.

    kudos to you, john mayer! (you must either have a really big heart or a really small dick)

  8. Police Chief Wilson

    Whoa, side boob!

  9. fame is funny

    definite downgrade.

    my god. that dress. jefferson airplane called, they want you to stop coming to their garage sales.

  10. schack

    oh, and can anyone say OOMPA LOOMPA DOOMPADIDOO? she’s even got the midget legs and the space suit!

  11. Whammer Jammer

    She has got to be the most overrated chick on the planet. Her rack is all she has, other than that, she is absolutely talentless.

  12. yaya

    Everyone leave Jessica Simpson alone! Not everyone is blessed with super perky breasts. Hers are real and natural and heavy and there’s nothing wrong with that

  13. LoneWolf

    Lindsay did the side boob thing months ago with a much better result. Poor Jessica, always behind the curve.

    Papa Joe needs to step up the career path. I guess next we’ll be seeing some panty-less crotch shots, followed by a report of her “falling asleep” in a club that’s blasting dance music at top volume, and then finally she’ll enter rehab. Maybe she can squeeze a teary train wreck of an interview with Matt Lauer in there somewhere too.

  14. gwb

    that mayer is a total wiener.

  15. schack

    they’re not real. the WERE real, until she lost a bunch of weight, which was THE marketing scam for that stupid bumble-hick movie, and she had to have them lifted with implants. GOD, don’t you read your celebrity news?

  16. Pat

    I’m pretty sure that when they get home, he can insert a little crack-handle between her shoulder blade and raise her implants back up. That one was Joe’s idea. He plays his “boobies go up, boobies go down” game in front of a mirror for hours and hours. Sadly, she laughs every time.

  17. pixelbasic


  18. Richard

    Her tits rock. Superficial is insane. She’s hot as hell and her body is amazing. Her worst pictures, at her worst weight, are still better than 90% of what’s out there. She’s annoying and dumb as hell, yeah, but that’s a different story.

  19. RussianMafia

    Third picture, top:

    His pimply razor burn scruff!

    If you’re dating Chestica, go get a facial or somethin

  20. cardio

    What the hell is wrong with what she’s sporting? Ok, they’re not the perkiest, but Christ, I’d love to knock those things around all day! I definitely could give her the old pearl necklace after going between them for a while. And how good would she look with the Cincinnati bowtie I’d give her?

  21. ttime0057

    Jessica’s breast look the way they do from the side because that is what REAL breast look like. Everyone is so used to seeing breast implants that they forget what REAL breast look like. They are not saggy, they are REAL.

    Now, after making that point– I HATE Jessica and have lost all respect for John Mayer!!

    Why do all of these seemingly intelligent men fall for that tranny-looking airhead?

  22. PrettyBaby

    Fuck people those tits are not fake! I have natural big tits and no matter how slim I get, they stay big. Good God, the idiocy around here sometimes.

  23. RussianMafia

    She had implants, she did. Not for increasing size, rather for lift. Its a fact. (Incidentally its a difft sort of implant)

  24. cardio

    @22 – big natural tits are a huge fucking turn on. You can tell hers are natural because of the sag (which is also part of the turn on). How do you “stack” up to her?

  25. jesseeca

    who cares about her boobs, look how orange she is the bottom row first picture. yikes!

    i never understand how these people don’t make sure their clothing fits before they go out in public.

  26. ph7

    She’s the type of girl that is a lot of fun to bang of few times (Particulary rowdy, drunking fucking) but then you get very tired of her because she so incredibly stupid.

  27. hendero

    now I’m no Tom Ford (although the supermodels I dress every morning tell me otherwise), but why would anyone design a dress which a) provides no support for your boobs; b) exposes half of your boobs and c) makes wearing a bra out of the question? I understand sagging is “natural”, but if you’ve built your career on your tits having them drooping like Deputy Dog’s face ain’t the best move ever.

  28. cayana

    I can’t pay attention to her boobs when her skin is BRIHGT ORANGE. It’s disturbing. She reminds me of the news story I read about a little girl who drank 2 gallons of Sunny Delight every day and eventually all the orange dye from it went into her skin.

    Also I think her dress is the NBC logo, upside down.

  29. PrettyBaby

    #21 Well cardio…. I am not sure Jess’s size- she looks to be a D cup though and that is me as well. But don’t tell anyone… it can be our secret…

  30. Jacquelantern

    Apparently, Jessica has been taking some hair styling tips for John… ever since here hair has looked like shit! Well all toghter she looks like shit lately… I think it has something to do with him. She is in the syndrome of… Oh I have boyfriend… I can don’t have to look good anymore. Never a good idea… he’ll dump her ass.

  31. Pointandlaugh

    real boobs are over-rated. Give me a chick with boobs (real or fake) that are so perky that she can walk into her bra, like a handshake. Yeaaaaah baby.

  32. cardio

    PrettyBaby – I can keep a secret. For instance, I’ll never tell anyone what I’m doing while imagining my face motorboating those D’s.

  33. mslilypond

    Even if she had a breast lift, all that does is make them perkier it doesn’t increase size. Also it doesn’t last if you have heavy breasts. I think hers may have given out.
    Mine are about the same size though (papa joe would be just as proud as my DD’s)
    and don’t sag as much as hers seem to in that shot. That dress isn’t doing much for her rack. She’ll have breasts to her knees if she doesn’t start supported them.

  34. 86

    The both have Quozz faces.

  35. DrBob2607

    #20 – Cincinnati Bowtie ! Woo Hoo ! I’ve heard of that one before.That ranks up there with the old Cleveland steamer, the Dirty Sanchez, and my personal favorite – the angry pirate..

    Yaaharr, me buckos !!

  36. stickyKeys

    could someone please photoshop a cock in her hand in pic #5? Much obliged.

  37. 86

    If she doesn’t keep up with her cardio she will be resigned to wearing fat-girl clothes forever.. ie this dress.

  38. biatcho

    She’s gonna end up looking like that old chick, Magda or whatever her character’s name is, from There’s Somthing about Mary.
    Old, dried up, overly tanned with saggy funbags down to her vagina.

  39. cardio

    @37 – I keep telling her she needs to keep up with me!

  40. I’d still suck on them like ice cream cone.

    -Raekwon the Chef

  41. cardio

    Dr. Bob – she has the perfect rack for a good Cincinnati bowtie.

  42. shanonorato

    Her body certainly took a turn for the worst after the Dukes of Hazzard.

  43. karifarrell

    Why does everyone always knock John Mayer? I think he’s totally cute. I just don’t know what the hell he’s doing with JS, I mean sure she’s pretty enough, but DUMB AS A SACK OF ROCKS. And true, I never saw that Dukes of Hazzard movie, nor have I ever listened to one of her songs, so I don’t know if she has any real talent. But I’ve seen her on tv commercials and that thing about not knowing if she was eating chicken or tuna, and COME ON!!!!

  44. sol

    agreed, john mayer is pretty much the ideal man…for girls who are afraid of penises (or who have one themselves, as in jessica’s case).

  45. PrettyBaby

    #44 John Mayer= Quasimoto
    Jessica can do better. I put my vote in for the Viva Le Bam Gangbang Part II

  46. wedgeone

    #29 – PB, when do we get to see ‘em? We’ve been having this conversation for months! Even a court artist’s sketch would be good. Quit holding out on us.

    #36 – ROTFLMAO! That’d be a pretty thick piece of meat. Do you think John could be packing that much? Jess would be getting pretty stretched out from one that size.

    John Mayer does look like Bigfoot next to Jess. Is he like 7 feet tall or something? Hopefully, Jess will stay confined to John’s tour bus & not try & grace the stage with her lack of talent.

  47. bush twins

    It’s true, Jessica got a breast lift (not augmentation). Apparently she was confused and putting her thong on top and her push-up bra on bottom, so her breasts sagged. And now her clit is just below her bellybutton.

  48. PrettyBaby

    wedgeone- You are pushy, damn. (I sorta like that) Show your cock first, you and cardio and then I’ll compare. And you BETTER have a pink cock.

  49. PrettyBaby

    Just a little haha- inside joke there Baby, nevermind..

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