Pimpin’ Ain’t Easy


That’s Keith on the left, and Adam on the right.
That’s Sweet Uncle Willie in the middle.

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155 thoughts on “Pimpin’ Ain’t Easy”

  2. For a minute i thought it was one of those Monty Python ladies in the middle… thanks for clearing that up lol.

  3. I’m a little baffled as to what sort of comment one could post on this.
    Speechless, just speechless.

  8. Oh, Hmmmmmmmm,
    That is, without a doubt, the UGLIEST pimp outfit I have EVER seen. And I used to watch Starsky & Hutch fer cryin’out loud.

  10. At first I thought it was some sort of Christopher Columbus outfit. Nice hat dude. Goes well with the “looking-down-my-nose-at-you-peons” attitude. 🙂

  14. Uh. . .I dare you to replace the pic in the upper left of your site with a closeup of you in this one! C’mon, let the masses see the real Uncle Willie every day! Oh and I agree with one of the above posts. . .now we know what you did when Anne and the kids were away. heh.

  18. I don’t know what it is about that outfit you have on, but you kinda look like Winona Rider. Is it just me?
    You havn’t been out stealing dresses lately, have you?
    Daniel

  25. I am SO baffled as to why anyone – including you (the online Wil I usually agree with!) thinks dressing up as or being a pimp is a cool thing to do.

  27. Isn’t it obvious?
    If it’s good enough for Jesus, it’s damn well good enough for Mr. Wheaton (SIR!)

  29. Aaaaaaw, is a cute picture there, Wil. I like it! ^_^ But, you really don’t look like the pimp type LOL, sorry…

  30. Daniel, I was thinking the same thing!
    Too bad the photo isn’t in color so we could see the nasty outfit in all its glory.
    And Wil, you should have had the shirt open a bit more… I mean, if you want to get *into* the pimp thing, you gotta really go for it!

  34. OUt of vast curiosity why in this pictuture and in another picture on Adam’s web site does Wil look very stoned?
    -R

  37. That’s wrong! Just plain wrong!
    Have you been raiding your Great-Grand-Father’s dusty old chest again?

  38. I’m in love.
    I wonder if that’s what a younger Kyle MacLachlan would look like, all pimped out.
    I am SO pleased with that picture.
    And hot soup girl – that’s ok, we still love you.

  40. And finally, this week Bob Dylan revealed the inspiration for “Leopard-skin pill-box hat”.

  41. Think of all the polyester tigers that gave their lives for the sake of comedy…it

  42. Think of all the polyester tigers that gave their lives for the sake of comedy…it

  43. Think of all the polyester tigers that gave their lives for the sake of comedy…it

  44. So what the hell happened to your closet, and why the fuck were you in front of it when it exploded?
    And where’s the ‘hos? I wanna see the merchandise.

  45. Oh, and the title just proved that Sweet Uncle Willie (sir!) is a closet WWF fan.
    Hmmm…come to think of it, Sweet Uncle Willie might be a great name for a WWF manager, or something.

  48. OMG I can’t beleive that outfit. What pray tell was the sketch you were working on? You were working on a sketch, weren’t you?
    Well here’s to you Pimpin Sweet Uncle Willie.

  49. Does anyone else think Wil looks a bit like Sylvester Stallone in his early Rocky days here?
    Uh… Just me then…

  50. Ahhhh.
    I see the next entry for a Fark Photoshop contest right in front of me.
    I dare you to wear that outfit whilst playing Dodgeball with Tiffany on Wednesday! 🙂

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