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Bend on David Letterman

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In the opener for last night's Late Show with David Letterman, Bend was mentioned twice.

Is Bend all that bad, Letterman?

First, when Letterman joked that he was from Bend, after saying so he made a face that looks like someone just gave him a swift kick in the pants . Here's the video, quip at about 1:00.
Second, when he asked guest performer Tyler, the Creator about Bend, effectually saying, "Hey, did you get my joke at the beginning of the show?"

Fast forward to 4:55 in the video below where Letterman asks,
"Have you guys ever been to Bend, Oregon?"
Tyler responds, "Yeah, I don't even know what that is."