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. saintmaybe

    Holy shit–I don’t know whether to laugh or cry. On the one hand, this photo evidence makes me feel a HELL of a lot better about my sad excuse for a 40-year-old chest (which has, in truth, looked–AND FELT–equally sad since the day those puppies sprouted, sometime back in the 5th grade); on the other hand, the whole picture still SUCKS OUT LOUD, for the lovely Jessica and for me. Sigh.

  2. cardio

    PrettyBaby – it is pink, but I don’t have red hair, so it’s not an APW (abnormally pink weiner).

    And if I do show it, you’re going to want to surround it with those nice D’s of yours.

  3. angelesque

    I think she looks great here. And lookit that calf muscle!

    Good on ya, Jess.

  4. danielle

    Are those “boobs” or holding containers for liquified brain? It would make sense, seeing as though the twit has the IQ of a small insect. No wonder they’re huge.

    Gives a new definition to “brain drain”.

  5. DeezNutz

    Big natural tits are so 1980′s, the perfect complement to a big hairy bush. do yourself a favor and have those things downsized.

  6. katzie

    along with being slightly ditzy it seems shes loosing her eyesight… how can she date that monstrosity. he looks like he should have been a costar in the movie, interview with a vampire, hes so hideously fug. ugh. poor girl.

  7. I’m not a fan of Jessica, but hey, what can she do? As her father said “She’s got a set of Double D’s, there’s no hiding those puppies”

  8. PrettyBaby

    Didn’t her fucking Dad really encourage her to date this Fug?? What a Hitler that Joe is. A Molesting Hitler.

  9. RussianMafia

    She is bad in bed. Just lays there.

  10. Quantity IS quality… “saggy” is not in my vocabulary.

  11. DancingQueen

    Why do I suddenly get the urge to watch “Beauty and the Beast?”

  12. biatcho

    #61, I get the beast part. But Jon Mayer is hardly a beauty.

  13. XeoRad

    At least they are natural titties. I hate silicon. But she has no ass. She should work out with Jessica Biel and build up her pooter. That and a push-up bra and she will survive Hollywood for a few more years. Her sister actually looks better after surgery, but that’s not a hard thing, as she was one ugly little skank. An ugly little skank who can’t sing – live. SNL

  14. pookiedoo

    In the first couple of pics she keeps touching her ass. And the last picture, as she’s coming down the stairs, clued me in. The look on her face says it all–she crapped herself!

  15. Shanipie

    I couldn’t think of a more nauseating couple than that pretentious pot head pale clay formation of a human being and that man faced orange tinted skag.

  16. MorganKnowsBest

    I think it’s sad that we’re all here criticizing celebs…what are we doing here anyway? We care so much about them that we’re devoting some sort of time to them…we did, after all, write these comments ourselves, correct? I’m not saying I’m any different because I’m here too…but it just goes to show you that no matter what they do, they’ll always be the center of attention and we’ll always be intrigued by what they look like or don’t look like. ; )

  17. happy_bunny

    Don’t let her dad see pic #1.
    He’ll be flashing it around and bragging about the sideboob for years to come.

  18. kathleen170

    Eww tomato.

  19. You people blasting Jessica are morons. Jessica is the perfect woman.

    Gorgeous face
    Smoking hot body
    Dumb as a bag of hammers

  20. LL

    I don’t know about the quality of her ta-tas, but that ugly-ass dress is doing her no favors. As someone above said, no support, impossible to wear a bra with, the design is such that it makes her look twice as wide as she actually is. And yeah, if you have big ones, get used to wearing a bra, because if you don’t, those things will be hanging low before you turn 30. She’s not even 30 yet, but her boobies look sorta like they might be ready for some freshening. You can have perky small boobs and no bra wearing (sometimes) or you can have big boobs and almost never go without a bra, but you can’t lug around huge knockers and expect them to stay up without help. It just isn’t possible. Skin stretches. So get a freakin’ stylist who will forbid you to leave the house without a bra, Jessica. Damn.

    Oh, and she IS too effin’ orange. Goddamn, why do white women think orange skin is acceptable? Only if you have a liver disease can you walk around in public like that.

  21. In that last picture she looks like one of those
    blow up sex dolls.

  22. The-Guslet

    What happened to this girl? She used to be mildly attractive (in a generic tanned, blonde sort of way) and now she resembles an orange tranny with bad hair and dodgy taste in shoes, clothes and men. At least she’s consistent…

    Please God, don’t ever let this one hook up with Carrot Top…

  23. l3irdy

    Love #36!!! Perfect idea! Looks more like they airbrushed the cock OUT of her hands.

    First, are we just now noticing her saggy boobs? Cause I noticed them a few years back…

    Second, Mayer is a pretty intelligent, arrogant fella. So what the fuck? Do you think he fucks with her lack of intelligence? He’s got too! You all know he’s just in it for those “saggy” boobs. Don’t forget he used to “try” to bang Jennifer Love Hewitt.

  24. Shanipie

    Anyone who says Jessica Simpson is hot is a damn fool with shitty taste in women. She is not “beautiful” she is interesting looking. Thats all, she looks different than most people, that does not mean she looks good. There is not one thing about her that makes me go WOW! A lot of men think she is hot cuz well lets face it most men especially ugly horny ones, will think just about anything is hot.

    I think she looked good when she lost weight but that again is just her body, I think her face is awful.

    If you don’t agree I don’t care, your just blind and have crappy taste in women, thats all.

  25. diddleysquat

    She’s lookin real good in these pics… I love real titties, and ‘dem are some real big titties!

  26. FecalPellets

    LMFAO@NBC logo :-))

  27. FecalPellets

    The only thing I can’t stand about her are the crooked teeth.

  28. greeneyedcat

    I thought she had a breast lift…. did it expire?

    just because they’re real doesn’t mean they’re “saggy,” but this just isn’t a good look

  29. shofaz

    OMG she’s so f*ckin’ ugly…
    and fat.

    Who’d say that Ashlee would look better than Jessica someday. Now you see… she’s like… Ewww…

    Say NO to botox, guys. Say yes to boob lift…

  30. bootface

    damn i want to suck those titties

  31. I’d fuck the Papa Joe outta this bitch, long time, … if I wasn’t so into fucking dudes, that is.

    RPLTC in every conceivable way!

  32. lala

    why is no one commenting on the nosejob that she clearly had…..its so small and dainty, a far cry from the witch honker she had a few months ago…years ago (i suspect this is her 2nd) whats the matter jess…is ashley getting all of the attention with her pretty new sniffer???

  33. Just look at those boobies :p

  34. and what about her? she’s o.k.

  35. StoneRose

    dude, if you shot my tits from that angle, they’d look ‘saggy’ too, cause they’re real :P

  36. StoneRose

    btw, John Mayer’s forehead has become the new home to Frida Khalo’s monster unibrow in pic 7.

  37. Lowlands

    Oow,has Jessica Simpson giant saggy knockers?

  38. marme

    ugh I think I just puked in my mouth a little. I’ve seen cracked out porn stars look better than that. And ya her dress looks like a moo moo.

  39. lalalemon

    #70 Other things can loosen skin besides going braless. Like weight gain and loss (stretches it) and some people just naturally have bad skin elasticity.

    That said, large natural breasts are beautiful but they really should be in bras. I have a 32DD rack which looks kind of like Jessica’s and there are a lot of things you can wear with a bra. Even haltar tops if they are designed creatively.

    I actually think she has implants though. I saw that dr. 90210 show on E! and the creepy Dr. Rey said that implants can drop if you don’t wear your bra. Apparently there is some acceptable measurement about how much undercleavage one should have. Her old rack looked different; this one is plumper but still natural looking.

    And, yeah, for all of you that think real boobs are ugly, take a good hard look at your ballsack. THAT’S ugly.

  40. cole007

    how much do you want to bet that john mayer doesn’t really like her, but is going out with her to break her heart in retaliation from that tabloid-frenzy bullshit papa joe and her pulled when they went on one date months ago? anyone?

    Bad clothes, bad hair, bad tan.


  41. StoneRose


  42. uuhleesuh

    how the fuck are they saggy??? people are too used to seeing fake boobs.. although im surprised hers look real since she had fake ones.. but maybe she got them removed.

  43. danigirl

    i dont swing that way peronsally….i love guys…but my god…i would soooooo have sex with her…shes beautiful…..

    but john….i dont know….shes tainted now…


  44. Enano

    I have always thought she was strange-looking, and the only attractive parts were her long (fake) hair and her curves. But now her curves have obviously contracted cantaloupe-in-a-sock syndrome. The girl doesn’t know the difference between chicken and tuna, so how WOULD she remember the bra-putting-on-sequence? I see her as commercial and doing everything for show. Like she thought her career was going to take of and she could date anyone she wants, but she can’t. You don’t see Nick Lachey making a big deal about renting a room at her favorite hotel with his new woman. The only difference is one of them has class and one doesn’t, and I think a braless right boob sagging out of the gaping armhole of a sundress should answer the question, if there ever was one.

  45. vonka245

    thats a low blow. she is one of the ONLY ones who hasnt had a boob job. is it such a crime to not have fake ass tits jutting off your chest? i have natural breasts and THATS HOW THEY LOOK. comments like that spawn a whole new generation of self-hating women, is that what you really want? Or do you even care?

  46. bootface

    i’ve said it before and i’ll say it again – GOD DAMN I WANT TO SUCK THOSE TITTIES!!!!!!!

  47. well…mmm…i’d still to naughty things to them!

  48. I don’t care much for tits but i’d rather have them big and saggy like jessica’s rather than fake ass tits like some porn star.

  49. jenna

    does anyone has idea about how much is her size cup

  50. Matt

    saggy knockers my ass, I would suck on those puppies any day of the week!!!!

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