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 31, 2011

Charlie Sheen's word for general success in everything in life. Made popular in a Feb 2011 rant and subsequent interviews.
The only thing I'm addicted to now is winning, I had a disease and I cured it with my mind. Winning anyone?
by Shinra07 March 19, 2011

Pseudoironic exclamation almost exclusively used by corny frat boys and yuppies. The proper response is to sigh "chuh!" and turn away.
by J. Cryer March 29, 2011

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."
"this chicken tiki masala has a lot of win-namon in it, mmm."
by Thenameisbam December 30, 2007

What Charlie Sheen exemplifies.
by Mark Moyo March 20, 2011

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

A term made popular by Charlie Sheen representing extensive personal gain and accomplishment over others.
In some cases, it can also represent delusional egocentricity.
In some cases, it can also represent delusional egocentricity.
by Erck March 18, 2011
