Playmates and their cars over the years (30 Photos)

  • HoBoGuy

    First! #30 makes me happy 🙂

  • powersticks

    #27 is hot. Don’t like her car though.

    • Belisario

      # 27 – Sarah Jean Underwood ??

    • Bruno


  • dos santos

    It does get bitchier and bitchier with the years..

  • infamous9

    I’ll buy what ever #19 is selling!!!

  • ikindalikeapples

    haha 17 gets stuck with a jeep

    • Mustafa_Beer

      It’s comments like this, that make Bob switch around the order of the pics. 17 is now the vette in Greensboro. But I have NO problem checking out the chick with the Jeep

      • hmm

        why would comments like that make him switch around the order of the pics? To the contrary, comments like that should stop him from switching around the order of the pics.

    • WhatAnAssGasket

      Girls that like jeeps are awesome

  • astrowhiz

    Playboy must be more flush with dosh some years than others – #8 gets a DeTomaso Pantera #11 gets a 911 #18 gets a Countach.. and poor old Sara Jean Underwood gets a Mini Cooper

  • rando

    wrangler FTW

  • DThr33

    So you take all the pictures Jalopnik went and compiled themselves and don’t even give them credit for it? Fuck you, Chive.

  • jaynecobb2

    i like #18

  • aosux

    Chick on the bike…FTW

  • Anonymous

    #5 WANT.

  • Equalizer

    Ancient Chinese Philosopher once said: “Give a girl a car and it will spread her wings…”

  • 123roasthim


  • adde

    #9 is a rare Volvo p1800ES. Those cars are pure concentrated 70ties…. I like them…. and I like girls…

  • CHOO

    #7 is a boat, I’m very observant

    • observer

      I also observed that, then checked the comments to see if anyone else did. There is a motorcycle in this car gallery too…

  • zipperz

    #2 – is that a Sunbeam Alpine? Classic.

  • lolz

    heff is one lucky son of a bitch, I bet he did all of them…..ALL OF THEM

  • manguaco


  • Always Last


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