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A term coined by American actor Charlie Sheen on the news show 2020 March 1rst 2011 to describe his unique philosphy on life.
Winning by newguyinthehizzouse March 22, 2011
Wow. What does that mean? I'm bi-WINNING.

I'm so tired of pretending my life isn't perfect and bitching and just winning every second and I'm not perfect and bitchin'.

The only thing I'm addicted to right now is winning.
winning by RRCsteve March 22, 2011
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
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
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