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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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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win- (prefix) Added on to a word, usually a noun to describe the level of win, or awesomeness the word has.
"hey lets go to swagats. mmm win-dian"

"this chicken tiki masala has a lot of win-namon in it, mmm."
by Thenameisbam December 3, 2007
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A term made popular by Charlie Sheen representing extensive personal gain and accomplishment over others.

In some cases, it can also represent delusional egocentricity.
Good luck, you're gonna need it. I'll be over here like, WINNING!
by Erck March 3, 2011
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Congratulations!!!
You are the lucky winner of ANYTHING!!!

Now that you have possession of ANYTHING, you can do ANYTHING..
Show her, hold her, love her,
by Dreams789 January 20, 2023
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Catchphrase made popular by Charlie Sheen. Can be injected after any phrase.
Guy: Look at that crazy dude trying to carry 78 chickens in a grocery sack.
Girl: Winning!
(random outburst of laughter from all bystanders)
by krabo March 15, 2011
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