When someone is going through a self-destructing, downward spiral leading to a certain epic failure they may refer to it as "Winning." See also "Bi-winning"
by krazzzz2000 March 3, 2011
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When an action is done that is so mind boggling Win, one must stand off to the side, and give a round of applause. Most common when someone completes a task at over NINE THOOOOOOUUUSSSAAAAND!
Jack: Hey, I need you to hack the CIA.
Mila: Alright!

**FIVE HOURS LATER**

Mila: Well, I did it...
Jack: Good, good, what did you do to them?
Mila: I actually hacked the Chinese so they would think that the CIA hacked them. Thus causing a third world war.
Jack: You miss, are made of Win. I applaud you.
by Hellspam December 9, 2007
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Popularized by actor Charlie Sheen, after denouncing his employers of popular sitcom "2 and a Half Men" via multiple tabloid shit-storms, which resulted in cancellation of the show. The phrase "Winning" used by Sheen during interviews with various media outlets, was successfully repackaged and made further popular by SNL.
Man I totally failed my GRE today, but only because I was so high on coke throughout the whole thing...WINNING!
by PegLeggers March 15, 2011
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Pseudoironic exclamation almost exclusively used by corny frat boys and yuppies. The proper response is to sigh "chuh!" and turn away.
A random douche at a bar exclaims "Winning!" after taking a shot.
by J. Cryer March 13, 2011
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Charlie Sheen's word for general success in everything in life. Made popular in a Feb 2011 rant and subsequent interviews.
The only thing I'm addicted to now is winning, I had a disease and I cured it with my mind. Winning anyone?
by Shinra07 March 5, 2011
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What Charlie Sheen exemplifies.
I'm Not Bipolar, I'm Bi-winning!
Duh, winning.
by Mark Moyo March 5, 2011
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Someone who has a nice home shaved mullet and is just straight up steezy... usually a guy named andrew can be win.
by The Genius Sk8ter Not Hater November 3, 2010
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