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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!!!"
by dookeyboy March 30, 2011
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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!"
by PFabian187 March 22, 2011
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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.
by fingerboom March 25, 2011
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bi-winning

When you win here and you win there, you are in fact, bi-winning.

When you are bi-winning it is also possible to safely take large amounts of drugs.

You can also not die when you are bi-winning.
Charlie: I'm bi-winning. I win here and i win there. Now what?

Charlie: I probably took more than anybody could survive. You know. I was banging 7 grams of rocks, and finishing them, because that's how I roll

Charlie: Dying is for fools.
by ashleyboyo69 March 25, 2011
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It’s not about winning, it’s about sending a message

Phrase from the internet funny man himself, Alpharad. This means that styling on your opponent is much more important than winning the game. Usually used in Smash Bros.
Opponent: “Why did you go for that forward aerial offstage with no jump?”
Alpharad: “Because it’s not about winning, it’s about sending a message.”
by Tronix6114 August 19, 2022
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Winning

Being on the drug known as Charlie Sheen
by DragonSpawn March 28, 2011
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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.
by Rlvers March 28, 2011
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