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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!"

Charlie Sheen 

When someone has been on a multi day cocaine drug and alcohol binge; bender.
Joey didn't make it to work on Monday. I heard he pulled a Charlie Sheen so it doesn't surprise me.
Charlie Sheen by Roddyrama February 23, 2011

Charlie Sheen Syndrome 

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"

Charlie Sheen 

Charlie Sheen by gorblach April 14, 2011

charlie sheen'd 

cougar: im getting charlie sheen'd tonight!
charlie sheen'd by coug a loug March 24, 2011

dumb as Charlie Sheen 

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.
dumb as Charlie Sheen by needlenoots September 19, 2009