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!"
by Subzero88 April 26, 2011
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When a person gets paid much more than what they're objectively worth, thereby giving them a God complex. They become immortal and infallible in their own minds. Can often be seen in government employees and managerial staff.
You: "Can you please sign this paperwork?"
Boss: "I could...Or I could not, then blame it on you, then snort cocaine! MUAHAHAHAHAHAHA!"
You: "You really get paid too much for what you do...I suspect you have Charlie Sheen Syndrome"
by Darebearius March 3, 2011
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If someone is Charlie Sheening, he is always WINNING!! TO Charlie Sheen is very difficult as it requires Tiger Blood and saying it like it is i.e. I win here I win there I win everywhere.
At the last olympic games, Michael Phelps was really Charlie Sheening
by Olsted April 19, 2011
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a manwhore who is always drunk or high and has no respect for women
hes just like charlie sheen, a whore
by Clair H. June 10, 2015
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A walking STD who tries to seduce vunreable women.
Charlie Sheen has aids!
by RobotWizard June 29, 2016
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A chemical, drug-induced party sweat left in & on your clothing. Often after a party, but sometimes when you're at home watching internet videos at 5am.
After that New Years party, my blazer had a wicked Charlie Sheen.
by John Hollick December 31, 2015
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Stupid, dull-witted. The complete absence of rational thought or any potential for rational thought. The lowest possible level on the intelligence scale. A fucktard.
Student: Professor, this formaldehyde soaked frog I'm dissecting is dumber than Charlie Sheen.

Professor: Son, the correct expression is 'Dumb as Charlie Sheen' . It's not possible to be dumber than Charlie Sheen.
by needlenoots September 18, 2009
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