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If someone is Charlie Sheening, he is always WINNING!! TO Charlie Sheen is very difficult as it requires Tiger Blood and saying it like it is i.e. I win here I win there I win everywhere.
At the last olympic games, Michael Phelps was really Charlie Sheening
by Olsted April 19, 2011
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When one argues him/herself deeper and deeper into a hole, but in that hole, he/she is 'WINNING!'
Guy 1: Do you see him arguing that there are only eight planets? Doesn't he know he's wrong?

Guy 2: Yea, he's totally Charlie Sheen'ing it!
by DMacabre April 07, 2011
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