Monday Car…Toon-Up!

You clamoured. We answered. Here’s another cartoon from the pages of Playboy. Leave your best caption below!

This week’s winner will receive a Retrograde watch from Timex – the company is featured on pg. 44 of our October 2011 issue. This style has a detailed, textured dial with a retrograde sub-dial and a genuine leather strap. Sharp!

92 Responses to “Monday Car…Toon-Up!”

  1. Now this is Miller time!

  2. Mark Malinowski Says:

    I’m tired of soldiers saying officers have it made–the beer isn’t cold, and we have no mustard!

  3. Ever since Playboy has taken over, the USO has really step

  4. To long has it been since I’ve had the pleasure of a women and a cold beer. All we need now is the sweet sounding voices of Kevin and Andrea on the playboy morning show. And I can die a happy man.

  5. Comander stick it in my ass o by the way my name is merie from tiffany granith show

  6. Zach Tullous Says:

    Does this anal scene really require this uniform

  7. Chef-ryan Says:

    If I knew a halloween costume would get me this, I would wear them more often.

  8. I surrender!!

  9. This survival kit came with everything.

  10. I surrender!

  11. Merlin Chong Says:

    My. Name is G.I. Joe, lemme show you Kung Fu grip.

  12. Merlin Chong Says:

    My name is G.I. Joe, lemme show you my Kung Fu grip.

  13. Is that a miller in your pants, or your just happy to see me?

  14. Lets hope obama wasnt serious about this pulling out the troops talk

  15. Only a beautiful woman like you could make me stand and salute… While I’m sitting down.

  16. Thank me for my service? Thank you for your service.

  17. If I’d known AWOL stood for A Woman On my Lap I would have done this a long time ago

  18. How about A wub-wub Andrea

  19. Excuse me miss but I’m gonna need to occupy your fox hole.

  20. Baby, you need to cock my purple-headed-heat seeking-miosture- missle,so we can have a blast of a good time.

  21. greg callaway Says:

    The weekend worrior thing really paid off……

  22. why yes Gina I DO like to make my dick smell shitty.

  23. David MacNaughton aka tinythetrucker Says:

    “So Gina let me get this right” If I know all the words to can-can from Moulon Rouge you’ll give me a BJ while I finish my Schlitz. “sweet!”

  24. Thanks Kevin. This is much better than just a signed picture of Andrea!

  25. And I thought a peace corp mission to Uganda would be boring!

  26. …and to think, I thought my recruiting officer was lying we he told me this was what afganistan was like!!

  27. You have 71 other virgin friends and I do not have to blow myself up?

  28. Al-Qaida can keep their 77 virgins, I will gladly take my playboy playmate and a cold beer.

  29. I love it when I get care packages from home! Best one yet!

  30. Marik Laman Says:

    this is my kind of military insertion

  31. Gi joe & Barbie’s fantasy.
    Gi joe: I’m thinking Octoberbreast
    Barbie: I will hold your beer for you correctly.

  32. 1965tbird Says:

    Now that I won at know it or show it, lets play what’s in Andrea hole.

  33. ryandunlopski Says:

    Tell me again how you saved hawaii from the terrorists, captain klein!???

  34. I will need to see your rear area.

  35. Sir, are you a Staff Sargent

  36. And then I woke up. In Iraq.

  37. Wow!! When the Colonel said I’d have the best R&R ever, He meant it!

  38. I’ll trade my cameo for your camel.

  39. Really GI Stud…One More Facial And My Hair Might Stay Like This

  40. I find you guilty of having weapons of mass seduction!!

  41. The reason we lost at Vietnam.

  42. surrender now! you have been conquered the fleet has invaded you!

  43. boy i love the new playboy’s they send to the military

  44. Gaston Demers Says:

    Holy crap Gina you mean I don`t have to get you drunk to get anal !

  45. well don’t get to full of yourself, it’s not like you play a soldier on T.V.

  46. FischStix Says:

    I think im gonna like this new “dont ask dont tell policy”.

  47. Wow, this new MRE flavor really taste like the real thing

  48. Fuck you and your volleyball Tom Hanks!

  49. Steve noyes Says:

    She takes a licking and keeps on ticking me off.

  50. My God! They must have sent you to this island because of your huge nose to!

  51. Is that a gun in your pocket or are you just glad to see me 🙂

  52. “…and for my 3rd wish, I hope this NEVER ends!”

  53. So you say….Kadoffius is in the grotto at the Playboy Mansion

  54. Gina….Kevin was right, this is a great way to sex up Veterans day..nice job

  55. I love being Jaime Edmondson private bodyguard for theses USO tours.

  56. There is no need to look for wood to build a fire tonight you’re sitting on it

  57. Are you sure you are not too tired… You look a little fatigued.

  58. Now THIS is every mans fantasy island!! Fuck Ricardo Montalban and that midget!

  59. Are you sure you are not too tired… You look a little fatigued.

  60. My Timex isn’t the only thing I have on me that takes a licking!!

  61. Let’s play Army…I’ll lay down, and you can blow me up!

  62. Sooooo…what’s up?

  63. Message in a butthole

  64. OOOOO, I thought my orders were to invade the BEACH. This is much better!

  65. Why was Stalin so grumpy when the Red Party looks like you!

  66. Screw “genie in a bottle”, try me “In Gina’s butthole”

  67. I’m really glad you told me to take door #3

  68. AWOL ? Me?, No, I just heard you like men in uniform.

  69. damnit, that seagul just shit in my beer

  70. So this is where all the donations go

  71. Well kevin I was wrong about the whole “if you were te last guy on earth” thing

  72. Steve noyes Says:

    Haha jokes on you , I’m a flaming homosexual that’s why I’m dressed and you’re not you ugly non-gay slut. And Jerron suck. If that don’t win me a watch I don’t know what will!!!!!!!!!

  73. It’s great to be reminded about what we’ve been fighting for! This is the best Veterans Day EVER!

  74. junglejake Says:

    They were right! The more beer I drink the better looking the enemy gets!

  75. Well Hillary with most of the worlds worst Terrorists dead, we, in the
    Special forces have set out to slay more bush……..

  76. Your boots aren’t the only thing that is wet, Captian Stiffy.

  77. Jim from Traverse City, MI Says:

    Now this is what I call an enlistment bonus!

  78. Sure ill name the this hurricane after you!

  79. Seth DeLoach Says:

    Damn! I’m proud to be an American!!!

  80. ThirdWave Says:

    Man: “I wonder if she knows that’s an airsoft pistol?”
    Woman: “I wonder if he knows I used to be a man?”

  81. Don’t ask, don’t smell

  82. Half mast? No ma’am I’m at full attention

  83. Master Sargent said he was sending me to a deserted island tell I wined, wrong island, I’ll have desert and wine instead.

  84. Lady- The USO welcomes you to Camp Tittatwiddle, if you need any thing else press the buttons.

  85. Things were going great for Dave until he found out that the beautiful redhead had a.bigger hard-on than him.

  86. Now this is what I call US…Oooooo

  87. Fuck that 1 weekend a month and 1 week a year bullshit, if this is what it’s like, I will enlist full time!!!

  88. I love the smell of your buns in the morning, it smells like victory!

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