An ironic declaration that your behavior or life circumstances are an indication of your success, despite obvious failings that prove the contrary.
Charlie Sheen's rampant drug use, hospitalization and rehab for such, patronage of prostitutes, using strippers for child care, getting fired from his job and ranting against anyone who isn't on his side as "trolls," are all examples of how he is better than the average person and, in the game of life, is clearly winning.
by ClearlyLosing March 23, 2011

Wins is the common phrase used by small penis individuals who have won a game of Fortnite. The amount of wins a Fortnite player has determines how long there dong is (the more wins, the shorter dong)
by CameronDOTgov June 18, 2018

“Winning, anyone? Rhymes with winning. Anyone? Yeah, that would be us. Sorry, man, didn’t make the rules. Oops!”
by bananarchy17 March 21, 2011

An adjective for somone who surpasses the definition of Winning, therefore # is placed before the word.
Charlie Sheen is #Winning
by #Winnanator March 25, 2011

All Charlie Sheen and DJ Khaled do.
by OpTic ylleJelly May 15, 2011

something Charlie Sheen does.
“The only thing I’m addicted to right now is winning,” “Just winning every second,” “Winning, anyone?” “Duh, winning!”
by yssim999 March 17, 2011

To live a sex and drug fueled lifestyle like Charlie Sheen while banging seven-gram rocks in such a way that your brain fires in a way that’s maybe not from, uh… this terrestrial realm
WINNING!
WINNING!
Winning
by mmacado March 17, 2011
