The interesting thing about Charlie Sheen’s “Winning” quotable, is that it has been around in the Hip Hop lexicon for years.
It is a common slang term to express something good is happening to someone.
If you see your boy getting his pimp on with a couple of ladies in the club you would say.
“Tony is out here winning tonight.”
There has been several rap songs using the term, most recently DJ Khaled “All I Do Is Win”. Like many things that the hip hop community has created, the mainstream has been slow to pick up on it until Sheen started talking. I was on a conference call the other day when someone who shall remain nameless, but isn’t really hip said “they got their swagger back”.
Personally I think Charlie Sheen while having some legitimate issues, is also playing people and specifically the media like “puppets”. There is a method to his madness and watch he end up making millions off of it.
This spoof video of him playing Call of Duty is classic.
“I don’t sleep, I wait…Boom!!!”