Jessica Simpson. There was a time, man (30 Photos)

For more Simpson boobage, check out Complex.

  • darren

    If i walked into a room and saw 29, I'd probably need a change of pants

    • SweetAwesomeness


  • kevguy

    there was a time when what?

    • donalee

      remember in school. i think it was called a 'context clue'

      • dece

        unless he's alluding to a belief that there never was a time [of hotness/do-ability/etc]?
        in which case, my personal preference would agree that she was never "hot". do-able, sure.

  • Gulp

    Oh… my.. god… I actually still definitely would!

  • gator

    let the fapping begin……..

  • lkasjeroiafjwe

    I still would! i kinda like the larger ladies.

  • chrisdg74

    I'd still do her. Just as long as she left the mom-jeans at home.

  • Skedaddle

    red bikini and #30 takes me back…but nowadays? Not so much….

  • Hez26

    areola!…..feels like a win to me

  • Mr. Peen

    Thanks for the mammaries! 🙂

    • HellHath NoFury

      even though they weren't so great….

  • zym

    Sexual napalm!

  • aaa

    mother of god!

  • keithp420

    any girl that says she would toss your salad is alright in my book…

  • FapperX

    There was a time? There "IS" a time . . . I'd hit that like a home run. She may be plus size now but she's got a truck load full of money and it's only a matter of time before she's the next celebrity on Jenny Craig.

  • R. Wiggum

    That time is long gone my friend.

  • the past

    man those were the days

  • llama beans

    She's attractive for a woman with a pretty face, great figure and big tits.

  • mattythegooch

    Hoping in the Deloreon time machine and making things right!! #21 is crazy HOT!

  • HardCore Mike

    Man! What the hell happened to her!?!!?

  • Bobba Fett

    If she was smart enuf to know how to cook she might be the perfect woman.

  • jonnyknuts

    god she has a great rack

  • valleybronco

    holy crap! I didn't know she got fat, how'd that happen?

  • McBeastie

    At no time did talent or intellect ever enter the equation though.

  • nouu

    she looks better as a redhead, blonds just look slutty.

  • LT B

    It's nice to reminisce. Some people would have you believe that she is a normal size now.

  • robsterling

    Great boobs. And you just know that at one time they were covered in Nick Lachey's man-gravy!

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