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50,000 Monkeys at 50,000 Typewriters Can't Be Wrong

Pimpin’ Ain’t Easy

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

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16 April, 2002 Wil

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155 thoughts on “Pimpin’ Ain’t Easy”

  1. MobbyG says:
    17 April, 2002 at 11:33 am

    Hey Hey! Uncle Willie! That outfit looks great! I hear Dr. Detroit is looking for someone to join him at the head table of the Players Ball!
    Seriously though.. you be stylein’!

  2. Roger says:
    17 April, 2002 at 12:50 pm

    Hella Funny Uncle Willy…I agree this should be your main photo now!!!

  3. smhauthority says:
    17 April, 2002 at 1:09 pm

    Whoa.
    Dude.
    Weird.

  4. Slorge Gridlock says:
    17 April, 2002 at 1:15 pm

    Peter, Paul and Mary!

  5. dake says:
    17 April, 2002 at 2:04 pm

    I’m afraid. I’m very, very afraid.

  6. Mizzy says:
    17 April, 2002 at 2:39 pm

    lookin’ good wil, lookin good

  7. Danielle says:
    17 April, 2002 at 3:03 pm

    Rawwwr. Sexy.

  8. Tiana says:
    17 April, 2002 at 3:10 pm

    My hair looks like that on a good day. That’s way scary. Maybe now we should have instead of Wil’s posse, Wil’s hos….maybe not.

  9. hops says:
    17 April, 2002 at 3:37 pm

    big pimpin spendin G’s.
    How was dodging big willies balls today?

  10. Greg says:
    17 April, 2002 at 4:14 pm

    Huggy Bear would be proud!

  11. MattK says:
    17 April, 2002 at 4:27 pm

    This reminds of that episode where the Enterprise travels to the Planet of the Pimps and an away team consisting of Picard, Geordi, Wesley, and Billy Dee Williams has to go undercover to look for Huggy Bear.
    Oh….wait, that might have been a dream….

  12. Elkay says:
    17 April, 2002 at 4:35 pm

    BWAHHHH-Haaaaa-haaa!!! Wil, You are Dy-no-Myte! You and Dolomite can pimp with the best of them. Oh my God…I think I wet my pants.

  13. KJB says:
    17 April, 2002 at 5:08 pm

    Billy Dee Williams rocks.

  14. Space Captain says:
    17 April, 2002 at 6:10 pm

    Hot damn!
    Wil…that’s one of the greatest pics i’ve seen in awhile. a long while.
    does that make j.keith and andy your hos?

  15. Lady Bug says:
    17 April, 2002 at 6:16 pm

    The title to todays blog is “Pimpin’ Ain’t Easy.” I *know* that’s from a 80’s rap song – was it by Big Daddy Kane? Anybody out there know? Holla back, a’ight? (hee hee)

  16. Libby says:
    17 April, 2002 at 6:18 pm

    wil u look hot so old-time-ish

  17. RanZrox says:
    17 April, 2002 at 6:25 pm

    Uh Huh you said it,”Uncle Willie in the middle”.
    You look like my old high school chum in that Crazy pic.
    If dressin wicked like that is yo thang, so be it!
    Rock on Breaux,Dont let no one stop you!

  18. mudgirl says:
    17 April, 2002 at 6:53 pm

    Meow.

  19. Danie says:
    17 April, 2002 at 7:13 pm

    Umm…I’m typeless…speechless even…*scratching head*

  20. Norman Chan says:
    17 April, 2002 at 8:14 pm

    Har! that’s hilarious. and my co-workers ask why i read your blog. morons!
    wil wheaton. you are my hero.

  21. M Ha says:
    17 April, 2002 at 8:53 pm

    I’m so deeply upset by this picture. I looked at it earlier, and I left, horrified, only to return, as if pulled back by some maelstrom of ewwww.

  22. shanna/setf/y'know says:
    17 April, 2002 at 9:08 pm

    I’ve been oh so quiet for awhile now (not that I was ever loquacious anyway) but I had to comment.
    Sweet Uncle Willie, if I were a ho I’d want you for ma pimp. Youse fiiiiine.
    Okay, that’s all.

  23. pimp daddy kane says:
    17 April, 2002 at 9:17 pm

    Wicked duds… go check out my site

  24. hot soup girl says:
    17 April, 2002 at 9:22 pm

    Wil, you’re hired.
    Or,
    At least the hookers and doughnuts for the WWDN roadtrip will be easier to aquire than first thought.
    The hookers, anyhows.

  25. Warfeist says:
    17 April, 2002 at 9:40 pm

    All Right!! Go about your business, nothing more to see.

  26. MissKittyFantastico says:
    17 April, 2002 at 10:27 pm

    Spuds.. I disagree.
    It’s obvious that this picture(at a roadside cantina) is a ploy by Kraft to promote their new product- gravy flavored cake mix. I mean it’s obvious that this ad is trying to connect with a demograph of men who are most likely white male tourists that just visited Mardi Gras, maybe gay, and/or accountants, and all have had their suitcases stolen recently on their way to Vegas.
    I mean that seems the most likely to me.
    Hell the pay was prolly good (or it should be too look so pimpn’ good).
    But that’s just my two bits of lint and a guitar pick.
    -MKF
    “So I see your schwartz is as big as mine! Ha! So guys wouldya please go see Nova X?? They’re good. So go. and tell. Someone you trust.”- Bob Hamel, Drummer of Soulcracker.

  27. Eli says:
    17 April, 2002 at 10:31 pm

    So, uh, what’s the going rate these days?

  28. Spudnuts says:
    17 April, 2002 at 10:52 pm

    MissKittyFantastico said:
    >> It’s obvious that this picture(at a roadside cantina) is a ploy by Kraft to promote their new product- gravy flavored cake mix. I mean it’s obvious that this ad is trying to connect with a demograph of men who are most likely white male tourists that just visited Mardi Gras, maybe gay, and/or accountants, and all have had their suitcases stolen recently on their way to Vegas.
    All I want to know is where can I get me some of this cake mix?
    And…
    Where’s my MOTHERFUCKING SUITCASE?!

  29. MissKittyFantastico says:
    17 April, 2002 at 11:19 pm

    Spuds…
    Answer 1: Contact Harold (on http://www.soulcracker.com/board/index.php – Forum: Soulcracker Online – topic “Nefarious Tour Diary” posts under the name Jose Jones)
    Answer 2: My 8ball says: In Jonathan Brandis’ broom closet under all his copies of the Neverending Story II he still has.
    -MKF
    “hey bob, i’ll see you in seven hours. i think i’ve figured out a way for that other new song not to suck.”

  30. Dom says:
    17 April, 2002 at 11:25 pm

    oh my gawd .. yo all de beetches are going down to ten-forward the muscle with the crab on the forehead is the muscle and the guy with yellow eye’s takes the cash and big uncle willie keeps ’em all slapped down

  31. Spudnuts says:
    17 April, 2002 at 11:58 pm

    Jesus.
    Always with the “Soulcracker.”
    You sound like that fucker Spudnuts who always manages to work “Lakerboard” into every post.
    http://www.lakerboard.com

  32. TimTheEnchanter says:
    18 April, 2002 at 12:27 am

    You are the pimp Wil!
    Found a nice color shot on J. Keith’s site
    http://www.jkeith.net/gallery/pictures/080500e.gif
    Peace!

  33. MIAnne says:
    18 April, 2002 at 4:56 am

    Purple, I knew it would be purple….
    Thanks, Tim.

  34. Pat says:
    18 April, 2002 at 5:49 am

    hahahahahahaha.
    BEAUTIFUL, just beautiful!

  35. Antalya_AesSedai says:
    18 April, 2002 at 5:56 am

    For some reason, the pendant makes me think of Scrooge McDuck…

  36. WhosJeebus says:
    18 April, 2002 at 8:00 am

    This ain’t no Burger Kang, this the PIMP KANG! You gonna have it my way…bitch.
    Is it just me, or did anyone else think Wil was in drag the first time they looked at that pic?

  37. Nobadthing says:
    18 April, 2002 at 8:18 am

    Oh my Sweet Jesus. After spending quite a bit of time trying to digest this pic in black and white you had to put a link to a color version of Uncle Willie in pimp drag? This is most disturbing and I’m sure I will spend the rest of my day trying to come to terms with Wil and all that purple.

  38. MissKittyFantastico says:
    18 April, 2002 at 8:36 am

    It’s my home. My friend’s live there. We go places together and meet JB and KG together. It’s a loving bunch of drunk music fans.
    Plus there’s also this band who now lives in LA called Soulcracker.
    http://www.soulcracker.com
    (and I SWEAR to the Goddess that’s where this gravy flavored cake mix thing came from)
    Well since we’re on this music thing…
    You should listen to Black Rebel Motorcycle Club, Blindsyde, She Said Yes, Jimmy Eat World and support your local music scene.
    And Spuds.. I know you’ll appriecate this..
    I got my tv guide yesterday…
    oooh..
    There it was staring back at me…
    Bakula’s package
    never the cuties in the mail… just the package.
    the mail man is out to get me.
    Well I’ll just have to track down Uncle Willy’s cover now.
    -MKF
    “If anyone here is defiling the holy name of the Swaz, I will come to your house and crush shit.” – Ramsey

  39. Rachel says:
    18 April, 2002 at 9:02 am

    There once was a boy from outer space
    Who could vanish without a trace
    Only to show up strutin’ on the tube
    Dressed up like a pimp with too much lube,
    Until a borg chick comes and takes his place

  40. John Kenneth Fisher says:
    18 April, 2002 at 9:13 am

    Sometimes I think maybe I’m wrong. Maybe God does exist. And then I see things like this, and I know she cannot.

  41. adeversole says:
    18 April, 2002 at 9:25 am

    I’m not sure what to think about this. LOL!

  42. Kat says:
    18 April, 2002 at 9:34 am

    Hi Will!
    I haven’t left a comment in FOREVER, so I wanted to say hello. Hope all is well in your neck of the woods! 🙂

  43. Kat says:
    18 April, 2002 at 9:37 am

    Holy cow, you are HOT!! Huggy Bear couldn’t hold a candle to you in that outfit.

  44. angry penguin says:
    18 April, 2002 at 9:52 am

    Where’s your plume? Every pimp has to have a plume. Cool color pic.

  45. Sally says:
    18 April, 2002 at 9:53 am

    That picture really does leave you stumped as to what comment to leave. At first glance it looks like three freaks on parade. Thanx for clearing it all up, I was about to bust from laughing.

  46. jarrett says:
    18 April, 2002 at 10:28 am

    at first, i thought this was a reference to the segmemnt on pimping from this american life (shout out to my fellow npr geeks).
    but this is so much more amusing
    with my mind on my money and my money on my mind….

  47. Jeff says:
    18 April, 2002 at 7:21 pm

    Man, what a douche bag.
    HAHA JK I luv u! You gotta say that in a Conan, self-deffecating way. Me no spellgood.

  48. Bex says:
    19 April, 2002 at 1:51 am

    Wel Wil, “WHO’S THE DADDY”

  49. Oregoonie says:
    19 April, 2002 at 2:46 am

    Sweet Uncle Willie looks a teensy bit like Marc Bolan in that picture.
    Rattlesnake out with your tail feathers high. Jitterbug left and smile to the sky.

  50. jodilyn says:
    19 April, 2002 at 5:41 am

    Did you bring that outfit from home?

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