Sheen Winning.

Boasting or having an inordinate amount of hubris for one's self, even when it's perfectly obvious to everyone else that it is absurd and undeserved. Often associated with severe denial, ala Charlie Sheen.

"John is walking around gloating like he singlehandedly won the big game for us, when he spent 58 minutes on the bench."

"Yeah, he's totally Sheen Winning."

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Charlie Sheen Winning

Charlie Sheen Winning (also known as CSW for short) Is a disorder in which one feels that no matter what they do, they are always "winning" at life. CSW is quite similar to insanity except with CSW, you KNOW you're being crazy. You just don't give a fuck.

Micheal: "I have two porn star girlfriends who watch my kids and cook food while I do some nasty things to them in the bedroom! And I have NO idea what to buy next!"
Zack: "Damn man, you must be Charlie Sheen Winning!"

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