The Letterman Podcast

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.

Episode 182 – Mark Malkoff: “Love, Johnny Carson”This week marks the triumphant return of Mark Malkoff, released just one day after his brand-new book, Love, Johnny Carson, officially hit store shelves — both digital and delightfully physical.In this special two-part conversation, Mark and Mike dive deep into the world of The Tonight Show Starring Johnny Carson, exploring the legacy, influence, and pure magic of the era that defined late-night television. Mark opens up about the research and stories that shaped his book — including brand-new insights about David Letterman, and how Johnny’s Tonight Show helped forge the late-night landscape that followed.Together, the two compare and contrast the genius of Carson and Letterman — the similarities, the differences, and the unshakable threads that tie their work together. It’s a thoughtful, entertaining deep-dive into two of television’s greatest giants, guided by one of late-night’s most passionate historians.Before you do anything else, swing by Hello-Deli.com — the only place on Earth to get officially licensed Late Show with David Letterman merchandise, straight from the legendary Rupert Jee himself.And if this episode made you laugh, learn, or feel even a tiny spark of nostalgia, please like, share, subscribe, and leave us a glowing comment — or a mildly amused one, we’ll still frame it.

Episode 181 – The Return of J RyanThis week marks the return of our very first friend of the show — J Ryan.Before The Letterman Podcast even launched, J was part of the foundation, helping set the tone for what this show would eventually become.In this episode, Mike and J reconnect after both navigating some major challenges over the past year. Their conversation covers everything from personal growth and resilience to the exciting creative projects now lighting up J’s world — including his return to hosting Late Night Playset and co-hosting the sensational new podcast “A Blockbuster Year: 1985”, a nostalgic deep dive into one of cinema’s greatest eras. Oh, and yes — he’s also selling Batmobiles.Naturally, the discussion turns toward the state of Late Night itself — and, of course, to Mark Malkoff’s much-anticipated upcoming book Love, Johnny Carson.Swing by Hello-Deli.com — the one and only spot to snag official Late Show with David Letterman merchandise, courtesy of the incomparable Rupert Jee.And if this conversation brings you even a sliver of joy, please like, share, subscribe, and leave a positive comment — we promise it helps more than you know (and it feeds our fragile podcast egos).

Episode 180 – A Tribute to Arthur KellyEpisode 180 of The Letterman Podcast is a heartfelt tribute to our dear friend Arthur Kelly, who passed away around the Fourth of July.For 15 years, Arthur was the receptionist on the 12th floor of the Ed Sullivan Theater office building — Dave’s floor. His job was to be the gatekeeper: ensuring the right people and calls got through, while keeping the chaos of show business at bay so the brain trust could focus on making television magic.A few years into his tenure, something strange and wonderful happened — Arthur became an on-air personality. In a recurring segment dubbed “Coach’s Corner,” he portrayed a hilariously unhinged version of football Hall of Famer Mike Singletary, barking out locker-room-style motivation that instantly became a fan favorite.Arthur was also one of the first staff members to befriend Mike, and he holds a special place in the history of The Letterman Podcast. In this emotional conversation, Mike sits down with Arthur’s brother, Andre, as the two reminisce, share heartfelt stories, and reflect on the kindness, humor, and heart that Arthur brought into every room he entered.On behalf of everyone who considers themselves an enthusiast of the broadcasts released by David Letterman and Company, we extend our deepest condolences to Arthur’s family, and to his Late Show family, whom he cared for so deeply.We would also like to thank Worldwide Pants for allowing us to include a few classic clips of Arthur from Late Show with David Letterman in this tribute.Stop by Hello-Deli.com — the only place to find official Late Show merchandise, brought to you by the legendary Rupert Jee.And while you’re at it, give this episode a like, share it with a fellow fan, subscribe to the show, and leave a kind word or two — we’ll take all the positive reinforcement we can get.

Episode 179 of The Letterman Podcast features Andrea Engelsberg — a former Late Show with David Letterman intern who had a front-row seat to the magic during one of the show’s hottest eras.In what feels like a nostalgic sugar rush, Mike and Andrea (who snack on candy throughout the episode) dive into her journey as a dual U.S./Canadian citizen who landed the coveted internship during the “last hurrah” of an era where most of the Late Night staffers who had made the jump to Late Show were still on board. Andrea soaked in every incredible moment from the inside.From hilarious tales of her chaotic New York living situation to legendary behind-the-scenes memories, Andrea shares it all — including the time she braved the line at the Soup Nazi to grab lunch for the entire Late Show writing team. And then there’s the unforgettable story of how a sprinting David Letterman, in his pre-show adrenaline ritual, collided with Andrea in the hallway… resulting in a brand-new staff rule.It’s a joyfully unfiltered, candy-coated romp through one of the most exciting chapters in late night history — all from someone who was lucky enough to live it.Then: • A sweet shoutout to our only sponsor, Hello-Deli.com — still the only place on the planet (and the web) to grab official Late Show merch from Rupert Jee, Letterman’s favorite deli man. • Followed by our traditional plea to like, share, subscribe, and leave a glowing comment… or even a lukewarm one (we’ll take it — it still helps with the algorithm).

In this special emergency crossover, Johnny Mac (Daily Comedy News) and Mike fire up the mics to tackle the growing storm surrounding Jimmy Kimmel’s indefinite suspension from ABC. With conflicting headlines, regulatory noise, and media blowback in every direction, it felt like the right time to take a step back and look at what’s really going on here.Johnny brings a sharp, informed perspective on the FCC’s involvement, and together, he and Mike unpack the broader implications this moment has for the late-night genre. From the evolving role of hosts to the tension between punchlines and political pressure, it’s a conversation about where the line is — and whether it’s moving.They also talk about legacy, precedent, and how moments like this could shape the future of late-night television, for better or worse.⸻🛍 This episode is proudly sponsored by Hello-Deli.com — home to the finest official Late Show with David Letterman gear, served up by the legendary Rupert Jee himself. Buy something or risk disappointing Dave.💬 If you enjoy this chat (or even mildly tolerate it), please like, share, subscribe, and leave a comment. We frame the good ones. We also frame the bad ones — but we hang them in the bathroom.

Episode 177 – Friends of the Show with a Surprise Visit from Mark Malkoff!In this fun-filled “Friends of the Show” edition of The Letterman Podcast, Mike is joined by returning favorites Darin Cox, Allison Lips, and Adam Unger—but this roundtable takes an exciting turn when a very special surprise guest drops in: the mighty Mark Malkoff!Mark—host of The Carson Podcast, celebrated stand-up, and author of the upcoming book Love Johnny Carson (coming October 2025)—joins the conversation and brings his signature insight and passion for all things late night. The panel dives into Mark’s latest work and the legacy of Johnny Carson, while also exploring the ever-evolving landscape of late night TV.Inspired by a recent LateNighter.com article discussing dream guests for My Next Guest Needs No Introduction with David Letterman, the group shares their own ideal picks and discusses the cultural footprint of Dave’s Netflix series.As always:•our only sponsor, Hello-Deli.com — the only place to get official Late Show with David Letterman merchandise, courtesy of the one and only Rupert Jee. Seriously, it’s all we’ve got!Please like, share, subscribe, and leave a glowing comment… or a mediocre one. (We’ll still print it and hang it on the fridge.)

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.

Episode 175 of The Letterman Podcast is our quintessential summer vacation episode — and we mean that literally and hilariously.While spending time at Irene Hoffman’s stunning generational property by the sea in Greece, three beloved friends of the show — Rupert Jee, Irene Hoffman, and Steve Young — decided that a Letterman Podcast must be done. And what a delightful episode it turned out to be!Mike connects with the gang as they recount their Mediterranean adventure, including highlights of their trip, the laughter they shared, and the creative magic that struck while they were basking in Grecian sunshine. Steve, known as one of the all-time great writers from Late Show with David Letterman, continues to evolve as a brilliant and absurd performer, and this scenic getaway only amplified his creative genius.This is a relaxed, joyful, and thoroughly entertaining installment that reminds us how the Letterman family keeps finding ways to surprise and inspire — even halfway across the world.This episode is brought to you by our only sponsor — the legendary Hello-Deli.com — the one-stop shop for official Late Show with David Letterman merchandise, run by the one and only Rupert Jee.If you enjoyed this episode, we’d love it if you’d like, share, subscribe, and leave a positive comment. We know there are a million podcasts out there, but only one has this kind of beautiful nonsense — and only one of us is still paying off the Greek yogurt bar tab from this recording. Opa!

Episode 174 of The Letterman Podcast features the triumphant return of Johnny Mac, host of the Daily Comedy News podcast.In this special mashup episode, two late-night–loving forces collide as Johnny and Mike dive deep into the current state of the genre. With Stephen Colbert’s exit looming large and a whirlwind of speculation sweeping through the comedy world, there’s no shortage of hot topics to unpack.The conversation includes thoughtful (and occasionally hilarious) takes on the future of every major late-night host, a look back at recently resurfaced comments from Jay Leno, and of course, some insight into David Letterman’s reaction to the latest chaos.This isn’t about one show — it’s about an entire genre seemingly slipping through our collective fingers. Speaking of icons, our only sponsor is the legendary Rupert Jee at Hello-Deli.com. Get your official Late Show with David Letterman merch while you still can — mugs, shirts, and a slice of nostalgia. And if you’re enjoying the show even half as much as we enjoy making it, please like, share, subscribe, and leave a glowing review. Or a mediocre one. Honestly, at this point we’ll take anything with punctuation.

Episode 173 of The Letterman Podcast is a spontaneous mashup for the ages!Mike was about to appear on The Alex Bennett Program when his phone rang. On the other end? None other than former Late Show with David Letterman executive producer Robert “Morty” Morton. When Mike told him what he was about to do, Morty asked, “Can I join?” — and just like that, this one became too big for just one show.What followed was a spirited, thoughtful, and wildly entertaining three-way conversation. Alex and Mike both asked Morton about his time working with Letterman, as well as his take on current events — including expert insight on the unfolding situation at CBS and Stephen Colbert’s future at The Late Show.The spontaneity made it even more special, and we’re thrilled to share this unique crossover experience with our audience.And speaking of legendary institutions, don’t forget to visit Hello-Deli.com — still the only place on the internet to grab official Late Show with David Letterman merchandise, proudly run by Rupert Jee himself!If you enjoy the show, we’d be thrilled if you’d like, share, subscribe, and leave a positive comment. We’re just a humble podcast built on passion, nostalgia, and self-deprecating charm — so help us keep the magic alive!

Episode 172 of The Letterman Podcast features the return of writer, oral historian, and the official Andy Kaufman historian, Andrew Buss!Among Andrew’s many creative accomplishments is I Am McLovin, the definitive oral history of Superbad, but this episode focuses on another icon of boundary-pushing brilliance — Andy Kaufman.Andrew and Mike go deep into the newly released documentary Andy Kaufman Is Me, reflecting on Kaufman’s legacy, performance style, and ongoing cultural impact. They also discuss Andrew’s latest oral history in Vanity Fair, where he once again interviewed David Letterman, as well as entertainment powerhouse Dwayne “The Rock” Johnson, and others, about Andy’s influence on comedy, character, and the unexpected.It’s a passionate, funny, and thought-provoking conversation about an artist who blurred the lines between reality and performance — and continues to inspire generations.⸻ This episode is brought to you by our friends at Hello-Deli.com — the only place to get official Late Show with David Letterman merchandise. Say hi to Rupert… and maybe buy a magnet or two while you’re there. If you’re enjoying the show, please like, share, subscribe, and leave a positive comment. It helps a lot… and Mike swears every new subscriber gives him just enough serotonin to carry on.

Episode 171 of The Letterman Podcast features a very special guest: Jed Rosenzweig, the founder and driving force behind LateNighter.com — the definitive online resource for all things late night television.Jed and Mike have a wide-ranging and passionate conversation that touches on his early professional days working at Yahoo! during the infancy of the internet, his time with High-Def Digest, and how those experiences led him to create LateNighter.com. They also dig into Jed’s personal journey as a lifelong fan of late night television — from growing up in New York and attending tapings of Saturday Night Live and Late Show with David Letterman, to his observations on the evolution of the genre.Jed opens up about the challenges and victories of building LateNighter.com as a startup, assembling an incredible team including esteemed journalist Bill Carter and Mark Malkoff, host of Inside Late Night. Together, they discuss the site’s mission, the state of late night in 2025, and where the format may be heading next.📦 Brought to you by our one and only sponsor, Hello-Deli.com — the official source for Late Show with David Letterman merchandise, run by the legendary Rupert Jee. Buy a mug. Seriously. We’ll wait.👍 Like, share, subscribe, leave positive comments, and send good vibes. We run on nostalgia and coffee, and we’re currently low on both.