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I really think the case of Dennis Miller is a sad one. Miller was, at one point, an extremely intelligent comedian, albeit one who had to use big words to cover up for his own self-hatred. He was funny often, and he had very pointed criticisms of both political parties. But it wasn't enough. He was, for all his wit and intelligence, never able to charge the pure energy and emotion of his heroes Carlin and Pryor - no matter how shocking he wanted to be, he couldn't really provoke the way he wanted to, especially not after the passings of a pair of great Texan comics, the scathingly funny Sam Kinison and the brilliant Bill Hicks (my personal favorite standup).
And then he saw that even HBO was tiring of him. Dennis Miller Live stopped getting the push for Emmys from the network, because HBO had a new show with the new Richard Pryor, Chris Rock. Hell, HBO even started pushing for Mr. Show with Bob and Dave to get comedy awards over Dennis Miller Live. (BTW, if you like Mr. Show and haven't heard it, David Cross' SHUT UP YOU FUCKING BABY! is probably the best live standup recording since Hicks' Dangerous.)
And so he started to sell himself. He realized that in this day and age, it's hard being an outrageous comic - you have so much competition from brilliant young comics like Rock, Cross, Silverman and even from the old guard like Carlin. So Miller became an NFL color commentator - when he didn't know what he was saying, his audience didn't, and so he failed at that. Miller then saw 9-11, I think, as an opportunity to find an audience that didn't like the popular brand of outrage comedy (that is, the brand espoused by Rock, Cross, etc.) - angry white Republicans. He realized that angry white Republicans are, for one reason or another, the most outraged demographic in America, and he's run with it ever since.
The thing that Miller doesn't realize, though, is that he's lost any credibility he could ever have now that he's repping for the establishment. Good comedy has always been, even at its most polite, anarchism and saying 'fuck you' to the powers that be. Miller is a failure for the same reason the whole imported-laddie-culture magazine fad is a failure - it brutalizes and teases from a position of power. That's not outrageous - that's fascism.
My school had the option of inviting Miller last year, but ended up bringing Lewis Black instead. He was hilarious.
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