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 writers for Letterman, and the path that eventually led him into some truly memorable corners of the comedy world.That includes being on hand for Dave’s unforgettable Billy on the Street segment, shot and featured on Late Show just before Dave retired.Ritch also shares the origin story of Deathbed, which he co-founded with Ben Zelevansky and others, and talks about the unique creative lane it occupies — where comedy writers get to let their darker instincts roam. Mike and Ritch also discuss the latest story featured on the platform, written by none other than prolific Letterman writer Steve Young.To close the episode, Mike shares the full Billy on the Street clip discussed during the conversation, and we extend our sincere thanks to Worldwide Pants for the many ways they continue to support the show by allowing us to use these pieces of Letterman history.Then, as always, if you feel like doing something noble today, head over to Hello-Deli.com — the only place on Earth to get official Late Show with David Letterman merchandise, courtesy of the one and only Rupert Jee. A deli, a gift shop, a state of mind.And if this episode gave you a laugh, a memory, or even a mild smirk, please like, share, subscribe, and leave a positive comment. We continue to shamelessly ask because it works slightly better than not asking.

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 what he considers his favorite chapter from a remarkable 40-year run at 30 Rock. He talks fondly about some of his favorite musical moments, including seeing Sonny and Cher up close, mixing the show, helping mic guests for signature segments like Stupid Pet Tricks and Stupid Human Tricks, and working around the unforgettable performances that featured Paul Shaffer and the World’s Most Dangerous Band.It’s a warm, funny, and highly specific behind-the-scenes conversation with someone who helped make the chaos sound smooth.Before you go, make your way to Hello-Deli.com — the one and only home of official Late Show with David Letterman merchandise, lovingly maintained by the legendary Rupert Jee. Buy a mug, buy a shirt, buy a memory.And if you enjoyed this episode, please like, share, subscribe, and leave a positive comment. We’re not above asking. In fact, we’re getting pretty good at it.

Episode 188 – Vancouver, Part Two: The Show ItselfEpisode 188 of The Letterman Podcast picks up right where last week left off.In Part One, Mike, Len, and Rob recounted the unforgettable experience of meeting David Letterman — and even Paul Shaffer — before Dave took the stage at the Queen Elizabeth Theatre in Vancouver for his sold-out conversation with Zach Galifianakis.This week, the focus shifts to the show itself.Len and Rob join Mike once again for a one-of-a-kind report on a one-of-a-kind evening, as the three of them break down the entire event from top to bottom. They discuss the surprise appearance by Paul Shaffer, the tone and rhythm of Dave’s conversation with Zach, and a delightfully odd, very Andy Kaufman-esque bit that Zach may or may not have sprung on Dave in real time.If there’s a more complete account of this Vancouver appearance anywhere online, we haven’t seen it. This episode may well stand as the most definitive recap of the night — a David Letterman enthusiast’s-eye document of a truly special show.For David Letterman enthusiasts, this is the kind of episode that preserves the magic.Before you go, make a stop at Hello-Deli.com — the one and only home of official Late Show with David Letterman merchandise, lovingly kept alive by the legendary Rupert Jee. Buy something classy. Or weird. Rupert contains multitudes.And if this episode brought you even a fraction of the joy that the show itself brought our little Vancouver wolfpack, please like, share, subscribe, and leave a positive comment. We’re not above begging — but we prefer to think of it as charming persistence.

Episode 187 of The Letterman Podcast is the first in a special series focusing on David Letterman’s recent appearance at the Queen Elizabeth Theatre in Vancouver, British Columbia, where Dave sat down for an onstage conversation with Zach Galifianakis in front of a sold-out and extremely grateful crowd.But the story begins before the show.Mike and four fellow Letterman enthusiasts decided to head down to the venue early to see if lightning might strike… and if they might somehow get the chance to meet Dave.Joining Mike for the adventure were former podcast guests Rob Stover and Len “Lenny Bruce” Goldman, along with new friends James and Paul. What happened next turned into the thrill of a lifetime when the group not only met David Letterman, but Paul Shaffer as well.It was one of those surreal moments that fans dream about but rarely experience. The five-man “Wolfpack” walked away with memories — and photographic and video evidence — they’ll never forget.In this episode, Len, Rob, and Mike recount the entire story from start to finish, sharing the excitement, the disbelief, and the joy of a moment that every Letterman enthusiast hopes to experience at least once.For anyone who considers themselves a fan of David Letterman and the broadcasts created by Dave and Company, this was nothing short of a grand slam home run of an experience — and we’re thrilled to dedicate an entire episode to telling that part of the story.Next week, we’ll return to talk about the show itself… which was absolutely outstanding.

Episode 186 of The Letterman Podcast features Erik Akerblom, a man whose fingerprints — quite literally — are on every Late Show that ever came out of the Ed Sullivan Theater for nearly three decades.Since the mid-90s, Erik has been a trusted pillar of the technical maintenance and post-production teams at the Ed Sullivan Theater. There are only a handful of humans on Earth who know the building’s guts, gears, quirks, and secrets as deeply as he does.Focused heavily on post-production, Erik has watched every single show that emerged from that historic stage — whether Late Show with David Letterman or The Late Show with Stephen Colbert — and shepherded each episode safely into the broadcast center.Erik shares wonderful stories from both eras of the theater’s life, including: • His on-camera appearances • His child’s moment of glory in the annual Halloween costume segment • And the absolutely remarkable story of where he was — and what happened — the night David Letterman announced his retirement… a moment that changed the entire trajectory of Erik’s life.A fantastic behind-the-scenes conversation with someone who helped keep the lights on, the ship upright, and the magic flowing.⸻Need a souvenir from the greatest theater in late-night history?Swing by Hello-Deli.com — the only place on Earth to get official Late Show merch, proudly purveyed by the legendary Rupert Jee. (Tell him The Letterman Podcast sent you. He won’t give you a discount… but he’ll smile.)And hey…If you enjoy what we do, please like, share, subscribe, and leave a glowing comment. Or even a mildly pleasant one. We’re not picky — we frame them all the same.

Episode 185 – Zoe Friedman: Comedy Royalty on The Letterman PodcastThis episode features genuine comedy royalty: Zoe Friedman.If her name sounds familiar, it should — her parents, Bud and Silver Friedman, didn’t just open comedy clubs… they invented the modern American comedy club as we know it. The Improv, the clubs, the alt rooms, the entire stand-up ecosystem? That’s the world Zoe grew up in.Her first job in show business? Working at the thrilling circus known as Late Night with David Letterman, where she spent over a decade absorbing the craft, the chaos, and the comedy magic from the inside.From there she became an executive at Comedy Central and Warner Bros., and today Zoe stands as one of the world’s most knowledgeable and passionate experts on stand-up comedy — its history, its future, and the people who make it matter.She is also the co-founder of Comedy Gives Back, a nonprofit supporting comedians with mental-health resources, crisis assistance, and financial aid. Zoe and her partners built an organization that looks after the very people who spend their lives trying to make the rest of us feel better. It’s vital work with a huge heart.Zoe and Mike have a rich, thoughtful, and deeply entertaining conversation about her life, her years with Dave, the evolution of the comedy world she was raised in, and the mission she continues to champion today.⸻Before the episode rolls, stop by Hello-Deli.com — the only place on Earth to score official Late Show with David Letterman merchandise, kept alive by the legendary Rupert Jee, who remains undefeated in the field of being Rupert Jee.And please: like, share, subscribe, and leave a positive comment. Every little click helps keep this quirky Letterman-loving corner of the internet alive — and it keeps Mike from stress-eating a family-sized bag of Skittles.

Episode 184 – Darin Cox and the Chicago Late-Night ExhibitThis episode features our good friend Darin Cox, co-host of The Irritable Dad Syndrome podcast — and the very first guest to ever appear on The Letterman Podcast!Darin works with Antenna TV, one of the chief sponsors behind the brand-new exhibits at the Museum of Broadcast Communications in Chicago. Alongside the stunning Johnny Carson: The Centennial showcase, the museum also features “75 Years of Late-Night Television,” a sprawling celebration of the format that re-creates iconic sets and honors hosts from Jack Paar and Johnny Carson to David Letterman and Stephen Colbert. Running through early 2027, it’s a love letter to the art of staying up too late.Darin shares stories from his behind-the-scenes visit — giving us a sneak peek at both exhibits — while he and Mike veer off into conversations about Warren Zevon, Soundgarden, and plenty more. It’s a fun, warm, and deeply nostalgic catch-up with one of our favorite returning guests.Before you dive into this one, drop by Hello-Deli.com — the only place to snag official Late Show with David Letterman merchandise, lovingly run by the legendary Rupert Jee.And hey — if this episode made you grin, giggle, or groan in recognition, please like, share, subscribe, and leave a comment. We can’t promise fame or fortune, but you’ll definitely earn our undying gratitude (and maybe a sandwich).

Episode 183 – Mark Malkoff (Part Two): “Love Johnny Carson”This week brings Part Two of our encompassing conversation with Mark Malkoff, host of The Carson Podcast and author of the brilliant new book Love Johnny Carson.Picking up right where Part One left off, Mark and Mike continue their deep dive into Johnny’s incredible career and legacy — and how it all connects to the world of David Letterman. The episode opens with the story of the unexpected intruder who interrupted Johnny Carson’s very first Tonight Show, and traces his journey all the way through his final broadcast.Mark also sheds light on Johnny’s post-retirement years — a period often mislabeled as “quiet,” yet filled with creativity, generosity, and private moments that reveal the man behind the legend. Along the way, the conversation explores the parallels and contrasts between Carson and Letterman, two giants whose influence continues to shape late-night television to this day.Before you head off into late-night nostalgia, stop by Hello-Deli.com — the only place to grab officially licensed Late Show with David Letterman merch, personally delivered (almost) by the legendary Rupert Jee.And hey, if this episode made you smile, please like, share, subscribe, and drop a comment — even if it’s just to tell us your favorite Carson moment. We’ll take it.