The Letterman Podcast

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.