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A phrase started by the TV-show actor Charlie Sheen. This word can be used in describing anything that is great. "Not winning" is obviously used to describe something not as great.
Bob: I totally banged that hot chick, Ashley, last night.
Sam: Dude, that's winning.
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John: Man, I can't believe Samantha dumped me...
Ryan: I know, bro. That's not winning.
by chikkachea March 10, 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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30
A word overused by charlie sheen to label everything he does
Come Wednesday they're gonna be naming it Charile Bros not Warner Bros . . . duh Winning!
by winninggoddess4CharlieSheen March 10, 2011
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"When Daniel beat Jonathan in the "yo momma" contest, he was considered winning!"
by Tom Nashed May 09, 2008
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32
What Charlie Sheen is doing right now.
"Just winning, every day. Defeat not an option."

"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.”

Charlie Sheen is not bi-polar, he is bi-winning.
by Dell_Tron March 02, 2011
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33
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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34
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 03, 2011
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