by 
sm00z
ANSWERS: 36
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I'm a bit uncertain about what you mean with "singing cowboy", I don't think I've heard about that concept before (hey, I'm just a stupid Dane okay! ;) ). But, I just can't imagine Marilyn Manson as a cowboy... :S
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Cindy McCain.
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Richard Simmons.
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Snoop Dogg
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I dunno... *maybe* he can sing... haha
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Steve Urkel
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George Bush
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I have 3 me ,myself, and I
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PeeWee Herman.
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Sonny Bono........... If he were still alive.
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Tiny Tim (R.I.P.)
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Porky Pig ... Most especially if he tried to yodel !
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<---This guy...Lol!
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Wayne Newton
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The Ying Yang twins
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Jay Leno or David Letterman wouldn't fit the cowboy image nor the singer image.
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"Mister T"
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Hulk Hogan
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My friend, Josh
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Jay-Z
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Michael Moore Al Gore Any rapper
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Let's go the other way .... Luciano Pavarotti.
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i would make a middle of the road one... I can't carry a tune but i can drag one :)
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george w. makes just about the worst anything, so i vote him.
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Nancy Pelosi
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Singing Cowboy? Can't think of a terrible singer amongst them. Cowboy though I'd say Hopalong Cassidy as William Boyd didn't sing in any of the adventures. William Boyd did sing though and was pretty good otherwise.
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Jingles (Andy Devine): ;)
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Well ... John Goodman , Andy Rooney , or Wilford Brimley .
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Steven Hawking ... with that electronic speech device he needs to use, singing is just not an option ...
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Newton L. Gingrich
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Julio Iglesias
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Ian McKellen
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Lee Marvin (Paint Your Wagon). Then again he was a likeable character so it's easily overlooked.
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not would-did -lee marvin follwed by a close second lorne greene
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Tony Romo or most of the Dallas Cowboys. Walter Brennan?
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Gilbert Gotfried
El Soupy 
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