Sam Anderson does a very good job of explaining why Jay Leno wins the ratings war. It always has bothered me, more than such things should, that more people watch Leno than Letterman. But I can't argue with anything in this article. Especially,
Letterman seems to loathe his monologue. He performs it grumpily, as a duty, and most of the humor comes out of his apparent disdain for the jokes, half of which seem to send him into acute liver failure—he squints, grimaces, chokes back vomit, very nearly dies. This irony insulates him from the material: He didn’t write the jokes, he wants us to understand, and he’s not really behind them, he’s just the one stuck up there reading them. He’s a failed idealist; it can be painful, night after night, to watch him betray his own high standards.
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Late night show monologues usually suck. I don't blame him.
Why doesn't he write his own jokes then?