The opposite of fail; when something of awesomeness happens.
Did you see Bobby playing Halo last night? That was win.
by VmKid June 11, 2009
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During Charlie Sheen's "reinvention" of himself as a tiger-blood-dripping warlock, one of his favorite mantras is "WINNING!" This particular usage is most common on Twitter, where the pound symbol (#) indicates a trending topic to follow.
Face it folks, you just feel better when you say it. #WINNING

#WINNING! #teamsheen

RT @ParisHilton @CharlieSheen Hey Neighbor, I think I might have #Tigerblood ;) and I'm definitely #Winning! Can't wait for #Sheen's-Korner
by jimmyjohnbrown March 10, 2011
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originally used as a normal word in phrases such as "we win the championship" "I will win this trophy" etc. But since the rise of online gaming, it has been used more and more out of context, and has developed into a nerd slang term.

Instead of using proper grammar, these geeks say "win" every time they see something funny or amusing. (See example).

I do not know how this is a "cool" word, but like I previously said, it's nerd lingo.
Nerd after watching a Naruto marathon: This show is win!!
by doggyboggyboi July 28, 2009
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Wow. What does that mean? I'm bi-WINNING.

I'm so tired of pretending my life isn't perfect and bitching and just winning every second and I'm not perfect and bitchin'.

The only thing I'm addicted to right now is winning.
by RRCsteve March 7, 2011
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The recent bout of self-destructive behavior perpetrated by Charlie Sheen, as defined by the actor himself in the myriad of interviews he's given to the national press.
NBC's Jeff Rossen: "Charlie, you recently lost custody of your kids and got fired from your job as the lead actor on 'Two And A Half Men.' What's going on?"

Sheen: "C'mon, Jeff, isn't it obvious? WINNING!!!"
by dookeyboy March 14, 2011
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