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I don't know much about this, but I had the same question because the guy on the Letterman bit seems so weird. I Googled Singletary + David Letterman, and got an article which explains that Letterman is doing a semi-regular, fake interview with an actor portraying Singletary. It is not actually Singletary. I hope that helps.

The actor is named Art Kelly and has been in other skits as himself with David.

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Q: Is Mike Singletary skit played by an actor on the David Letterman show?
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