The Letterman Podcast

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191 Eddie Brill and the Last Late Show with Stephen Colbert

May 22, 2026

Episode 191 – Eddie Brill and the End of an EraThis week’s guest is a very good friend of the show and one of our original guests, Eddie Brill.Eddie — the former warm-up comic and comedy booker for Late Show with David Letterman — returns to The Letterman Podcast to discuss the end of an era: the closing of The Late Show on CBS.Eddie shares his thoughts on what it means for Stephen Colbert to be the one tasked with bringing the franchise to a close, and reflects on the enormous impact that Th...

190 Dave on Billy On The Street! Ritch Duncan Was There, And A Whole Lot More!

March 27, 2026

Episode 190 – Ritch DuncanThis week’s guest is Ritch Duncan — comedian, writer, former Weekend Update joke contributor, and one of the founders of Deathbed, the wonderfully twisted horror platform created by comedy writers.Ritch and Mike have a fantastic conversation about how Ritch found his way into stand-up, his time going to school in Indiana, and the enormous influence David Letterman had on him creatively. They also dig into his work with the Stangle Brothers before they became head wri...

189 Steve Singer worked for 30 Rock for 40 years, but his favorite were working for Late Night from 86-93

March 20, 2026

Episode 189 of The Letterman PodcastThis week’s guest is Steve Singer, who worked in the audio department at Late Night with David Letterman from 1986 to 1993, right in the thick of the NBC years. As a trusted member of the Studio 6A team, Steve helped shape the sound of the show night after night, handling live audio and contributing to what viewers at home heard during one of the most beloved eras in late night history.Steve and Mike take a lovely trip down memory lane as Steve reflects on ...