I've never gotten the "Leno is an automatic punchline" thing. Is he dull? Probably. Guess what else is? NETWORK TELEVISION.
Do I watch Leno? No. But a lot of people do. I'm perfectly fine with that. I don't feel the need to trash him to show my indie street-cred. It's fine. Relax. Hell, I came out on Team Jay during the whole Jay vs. Conan thing.
To be honest, I probably respect his craftsmanship re: writing jokes more than I'll ever like Letterman, whom I dissed way back here.
Was Leno ever the coolest kid in the room? No. But so what? Who is?
And have you ever been good at what you do for 20 years?
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