Winning!

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 15, 2011

Winning!

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 13, 2011

Winning!

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

Winning!

When things are going yor way or about to. ie: a large settlement coming your way, having two live-in godesses taking care of your children, making 1.8 million dollars per episode.

I'm going to sue for TONS, and have my two live-in goddesses take care of my children, AND get a raise at my job. Winning!

by Trblgrrl March 03, 2011

Winning!

(Verb) the process of doing something radical or awesome that most likely involves partying with porn stars and doing lots of drugs. Frequently used by actor Charlie Sheen to describe a radical moment in his life.

Dane: Dude this party is radical!

Paul: Yea man! have a shot!

Dane: *gulps shot*

Dane: Winning!

by PollioCrow March 11, 2011

Win-Win-Win

A solution to a conflict which not only benefits both parties involved, but also benefits the mediator for having successfully mediated a conflict. Deemed the most optimal result of a conflict and coined by Michael Scott in the Conflict Resolution episode (twenty-one of season two) of The Office.

Making the poster into a T-shirt and forcing Oscar to wear it was quite a win-win-win solution.

by Free6000Bush June 30, 2011

Win win

A term a smarmy salesman or manager uses to tell you that both parties have positive outcomes from a situation. This is rarely true. see Enterprise bargaining

So you see here we have a win win deal.

Oh yes of course, you take my old car for nothing, and i pay off this new one for the next 38 years, i am a winner then arent i?

by jamesbrown May 02, 2003