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Dave Chapelle, when it comes to skit comedy. As a Stand-up though, he's really just average.
My favorite Stand-up Comedian is Joe Rogan. A lot of people aren't even aware that he was and is a Comedian first, his other acting and hosting jobs aside. He has the right balance of social commentary in his routine.
Ultimately, good Comedians break down and expose societal idiosyncrasies, using comedy as a way of disarming us so that we can honestly consider these flaws without our usual prejudices in support for, or against, a particular issue or person.
Comedy is really a brilliant form of philosophy...one that is much more affective in bringing people to consider alternative viewpoints than is straight-forward debate, IMHO.
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The thing about money? It makes you do things that you don't want to do
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