Top Definition
Apparently Charlie Sheen is doing a lot of it and tweeting about it constantly.
Banged another two hookers and snorted 5 lines of coke. I really am #winning.
by celebrator1975 March 09, 2011
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
Charlie Sheen + #WINNING-
bang 7 gram rocks = # WINNING!

pints of tigers blood = # WINNING!
by brokenglass420 March 13, 2011
An adjective for somone who surpasses the definition of Winning, therefore # is placed before the word.
Charlie Sheen is #Winning
by #Winnanator March 09, 2011

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