By Esther Zuckerman
Updated April 02, 2015 at 02:13 PM EDT

Billy Eichner took a seemingly delighted David Letterman on one of his scream-y jaunts around New York City streets to ask an important question: What should Letterman should do after his retirement from the Late Show?

The segment, however, also raises some other good questions. For instance: What will become ofPaul Shaffer? (According to Letterman, he has “connections in Canada.”) And what is it like to play shuffleboard with Dan Rather?

Some advice for anyone who might find themselves being quizzed by Eichner and Letterman? Don’t mention The Tonight Show—unless you want to incur their wrath.

Billy on the Street

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