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Letterman Bumbles Awkwardly, Adorably, Hilariously through a 'Billy on the Street' Segment

By Dustin Rowles | Videos | April 2, 2015 |

By Dustin Rowles | Videos | April 2, 2015 |

With Letterman heading into the late-night ether in a few months, he did something rare for him over the last 15-20 years: He appeared in a remote segment. But it wasn’t just his remote, it was Billy Eichner’s “Billy on the Street.” Letterman said it was an “honor” to do the segment with Eichner, who has idolized Dave since his teens.

What’s fascinating about the segment, however, is how much it resembles one of Dave’s old Late Night bits, back when he used to go out and harass people on the street, or in drive-thrus (if YouTube had been around in the 80s, Letterman would’ve dominated). Of course, even on Eichner’s berating segment, Letterman’s midwestern politeness still seeps through: He wants to yell and play along, but there’s also that part of him that needs to say “Hi. How are you doing? Good to see you and thanks.”

Basically, it’s “Billy on the Street” with a dash of Indiana (but not the bigoted kind).

Speaking of Indiana, in addition to speaking to what an embarrassment Mike Pence is, Al Franken also encouraged Dave to run for the open Senate seat in Indiana next year. (Dave also said he’d be “buried” in Indiana, which makes me sad. Not because it’s Indiana, but because he’s old enough to entertain ideas about where he’d be buried).

Dustin is the founder and co-owner of Pajiba. You may email him here, follow him on Twitter, or listen to his weekly TV podcast, Podjiba.