Unequivocally winning, regardless of circumstance, conditions, or whatever anyone else thinks or does. You have beaten life. Drive on!
Me: Wow Chase, you're really boned with that felony drug conviction, divorce, and rape allegation.

Chase: I don't care I'm Charlie Sheening this bitch still!
by CcoXo March 29, 2011
To go to an event after having consumed large amounts of alcohol and/or drugs
Trey Parker: We were lie "oh lets not do this" but then we decided to Charlie Sheen it and we were fine.
Matt Stone: we were just sheening our heads off!
David Letterman: They were both Charlie Sheening pretty hard.
by girl193093 March 01, 2011
The ability to drink and do drugs while looking like a winner.

Taking the stigma out of using methamphetamine and crack.

Getting respect while being publicly intoxicated.

Putting the fun back into disfunction.
"How was the party last night? Did you have a good time?"
"I had a great time...I was fully Charlie Sheening it!"
by notoriousP November 19, 2013
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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