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Winning in various parts of your life. In response to the question of whether or not he was bi-polar, [Charlie Sheen] [spontaneously] concocted the phrase in reference to his lifestyle that includes an extremely high income, a lot of attractive women (many porn stars and hookers) that will have sex with him and partying with lots of illicit drugs (cocaine, etc) and alcohol and surviving it. In addition he has beautiful children that he loves, so he believes he is winning at both ends of [the spectrum] in reference to his life.
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