Just being to cool for ANY ONE; being better than everyone else. Also is now a famous quote by "Charlie Sheen."
Well lets just say you will never know what winning feel likes.
by Rlvers March 11, 2011

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An ongoing cycle of competence and achievement in various endeavors. You cannot win; there is only the continuous action of winning. In other words, banging 7 gram rocks.
Charlie Sheen: "Duh, winning! It’s, like, guys, IMDB right there, 62 movies and a ton of success. I mean, c’mon bro, I won best picture at 20. I wasn’t even trying. I wasn’t even warm."
by aphex350 March 03, 2011

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When a male successfully sleeps with a female of choice.
Female "hey Brandenn...let's get a hotel tonight"
Male "only if i am winning"
by you will never get this February 10, 2010

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A lifestyle pioneered by Charlie Sheen and practiced by those in Sheen's Korner. This exclusive society demands Adonis DNA and tiger-worthy behavior of its members. You are either winning, or you're with the trolls.
Roger Ebert: I could get a million followers like Charlie Sheen did, but my wife would leave me and I'd be a poor lonely sap like he is.

Charlie Sheen: Yeah, you really don't know lonely till you've gone to town on 5 chicks at once. Still winning, plan better.
by fingerboom March 09, 2011

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One of Charlie Sheen's many addictions.
I just snorted 3 lines of "winning" off a naked "winning."
by TheDoodler83 March 01, 2011

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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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Roughly synonymous with "getting your ass kicked". Winning! is often a result of pissing off everyone you know and getting canned. There is a fine line between Winning! and OD'ing! or Dying of some kind of VD! Side effects include being arrested and losing all respect.
Man 1: I just got fired for being an arrogant prick and abusing every substance known to man, such as alcohol, prescription pills, sex, and enough cocaine to keep Colombia's economy thriving. Not to mention the time I threatened to cut my wife's head of with a pen knife and mail it to her mom...
Man 2: Dude, your winning even more than charlie sheen.
by tigerblood15 March 13, 2011

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The Urban Dictionary T-Shirt

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