winning 

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!!!"

winning by dookeyboy March 30, 2011

Winning 

An ironic display of triumph over a situation that is, in fact, partly or totally self-destructive or harmful.

Example #1: "My kid got into Harvard and it'll cost me my entire retirement savings to send them there. WINNING!"

Example #2: "I'm a reasonably decent actor with a fat bank account, but I've chased two wives and five children away with out-of-control partying, drug use and violence that's laughable for someone my age. WINNING!"

Winning by PFabian187 March 22, 2011

winning 

A lifestyle pioneered by Charlie Sheen and practiced by those in Sheen's Korner. This exclusive society demands Adonis DNA and tiger-worthy behavior of its members. You are either winning, or you're with the trolls.

Roger Ebert: I could get a million followers like Charlie Sheen did, but my wife would leave me and I'd be a poor lonely sap like he is.

Charlie Sheen: Yeah, you really don't know lonely till you've gone to town on 5 chicks at once. Still winning, plan better.

winning by fingerboom March 25, 2011

Winning 

Being on the drug known as Charlie Sheen

I was bangin' 7 gram rocks, that's how I roll - WINNING!

Winning by DragonSpawn March 28, 2011

Winning 

Just being to cool for ANY ONE; being better than everyone else. Also is now a famous quote by "Charlie Sheen."

Well lets just say you will never know what winning feel likes.

Winning by Rlvers March 28, 2011

Winning 

A phrase used by actor Charlie Sheen to describe a plethora of feelings and attitudes. Can be used for both expressing excitement and joy, or used to answer a question.

Example A

(Charlie Sheen receives a suprise)

Charlie Sheen: Winning!

Example B

Reporter: Are you bi-polar?
Charlie Sheen: Psh. I'm bi-winning.

Winning by Shareeb4Prez March 18, 2011

Winning 

When a male successfully sleeps with a female of choice.

Female "hey Brandenn...let's get a hotel tonight"
Male "only if i am winning"

Winning by you will never get this February 22, 2010