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
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
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.
John: Man, I can't believe Samantha dumped me...
Ryan: I know, bro. That's not winning.
by chikkachea March 10, 2011
A philosophy of life where defeat is not an option. A way to emphasize an event you consider positive. Popularized by the actor/philosopher Charlie Sheen.
The sun is shining on me, winning!

That's some great crack cocaine, winning!
by DetoxTV March 03, 2011
Winning is what Darren Stoten is.
Whats darren doing?

by ninjaaaa-1337 May 29, 2011
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
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 12, 2011

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