176 How Dan Cashman Booked David Letterman As His Final Guest

Episode 176 of The Letterman Podcast features a very special guest: Dan Cashman, host of The Nite Show with Dan Cashman — a regional late-night institution in Maine that has welcomed thousands of guests over its remarkable run… including, most recently, David Letterman himself.Mike and Dan dive deep into the origins of The Nite Show, reflecting on the early days, its evolution, and the incredible team Dan has worked with over the years to keep the show thriving. Along the way, Dan shares stories of notable guests, behind-the-scenes triumphs and challenges, and the unique flavor of producing a late-night show in Maine that still embodies the traditional spirit of the genre.Of course, the conversation reaches its apex as Dan recounts the lead-up to — and the unforgettable experience of — hosting David Letterman as his final guest. From how it came together to what Dave was like off-camera, Dan generously shares a treasure trove of insights, making this a must-listen for any Letterman fan.⸻Before we go…• Don’t forget to swing by our good friends at Hello-Deli.com — the only sandwich shop in history that also happens to be the exclusive home of official Late Show with David Letterman merch. Rupert Jee’s got mugs, shirts, and more… and if you’re nice, maybe even a smile.• If you’ve enjoyed this episode, please like, share, subscribe, and leave us a kind comment. Or leave a sarcastic one — we’re not picky. Just engage in some way so we can trick the algorithm into thinking we’re a big deal.