The Letterman Podcast

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.

Episode 170 of The Letterman Podcast features our very special guest, Jordan Zevon. A gifted singer-songwriter in his own right, Jordan is also the son of the late, great Warren Zevon — the genius, the icon, the soon-to-be Rock & Roll Hall of Fame inductee.Warren Zevon was a brilliantly bright thread woven into the fabric of David Letterman’s legacy, appearing on the show more than 30 times as a guest, musical performer, and even stepping in as guest bandleader when Paul Shaffer was away. His work and wit were cherished by fans — and by Dave himself.Joining in the conversation is friend of the show and official Warren Zevon historian Adam Unger, who helps navigate this heartfelt and often funny discussion. Jordan opens up about what it was like being Warren’s son, shares personal insights into his father’s legacy, and recalls his own performances on Late Show, including a memorable one with The Wallflowers. This episode is sponsored, as always, by our only sponsor — Hello-Deli.com, your official source for Late Show with David Letterman merchandise, run by the legendary Rupert Jee. If you don’t go buy a mug, Dave might throw a pencil at you. If you enjoyed this episode — or even just mildly tolerated it — please like, share, subscribe, and leave a kind comment. It helps the show more than Mike helps himself to snacks between takes.

Episode 169 of The Letterman Podcast features not one, not two, but three of our favorite humans: legendary Late Show comedy writer Steve Young, our amazing sponsor and friend Rupert Jee, and his equally wonderful girlfriend Irene Hoffman.Steve recently debuted his brand-new one-man show, EGONT, at the sold-out Caveat Theater in New York City, performing much of this material live for the very first time. Rupert and Irene were in the audience, and Mike watched remotely—so the gang gathered for a fun, insightful chat about the show, its creative genesis, and what it felt like to bring it to life.Along the way, they also catch up on a few classic stories and even solve the mystery of SAGG peanut butter. Yes, really.And speaking of Rupert, don’t forget that he still runs Hello-Deli.com, one of the only places left to snag official Late Show with David Letterman merchandise. So grab a shirt, a mug, and one for your best pal while you’re at it.Now here comes the part where I grovel—please like, share, subscribe, and leave a positive comment so the algorithm will stop bullying me. Seriously, help a buddy out.#LettermanPodcast #DavidLetterman #SteveYoung #RupertJee #HelloDeli #LateShow #ComedyWriting #EGONT #CaveatTheater #SAGGPeanutButter #IreneHoffman

Episode 168: What’s Been Going On – Guest Hosted by Candace ChisholmThis episode of The Letterman Podcast is a little different, as Mike hands over the hosting duties to his wife, Candace Chisholm. With a few weeks passing since the last episode, Candace interviews Mike about what’s been going on behind the scenes.Mike opens up about his father’s recent hospitalization due to advancing dementia, a deeply personal struggle that has impacted their family and may lead to some changes with the show moving forward.The two also discuss their recent trip to Vancouver, where they saw The Found Footage Festival with Nick Prueher and Joe Pickett, visited the Banksy exhibition, and reflected on After Midnight going off the air, among other topics.This candid conversation gives listeners an update on both the show and Mike’s personal journey as he navigates this difficult time. Need official Late Show with David Letterman merch? Head over to Hello-Deli.com – the one and only sponsor of The Letterman Podcast! Like, share, subscribe, and leave a positive comment! Or don’t… but if you don’t, just know that you’ll be added to an ever-growing list of people who have ignored this request. It’s a long list, but it still stings.

This week’s guest is Fard Muhammad, a longtime member of alt.fan.LETTERMAN and a devoted fan of late-night television. Few people appreciate the culture of late-night as much as he does!Fard and Mike have an enthusiastic conversation covering a variety of topics, including Fard witnessing Conan O’Brien’s first-ever Tonight Show, his emerging YouTube channel, his favorite David Letterman moments, and much more.Of course, we couldn’t do this show without our legendary sponsor, Hello-Deli.com—the only place to get officially licensed Late Show with David Letterman merchandise, run by the one and only Rupert Jee!And hey, if you’re enjoying what we do, why not like, share, subscribe, and leave a glowing review? Or, you know, do the opposite and pretend this never happened. Either way, we appreciate you!

This episode features stand-up comedian Chad Riden, a longtime Late Show fan and an early member of the legendary online Letterman fan group, alt.fan.letterman. Inspired by Dave from the very beginning, Chad has carved out a career as a broadcaster, performer, and stand-up comic, sharing the stage with legends like Nate Bargatze, Ralphie May, Doug Stanhope, Tom Green, and many more.Chad and Mike have a lively conversation where Chad does most of the talking, and Mike does most of the laughing. Jumping between hilarious bits and hard truths, they discuss Chad’s deep-rooted Letterman influence, his encounters with Dave and Laurie Diamond, the comedians he’s worked with over the years, and much more. SPONSOR ALERT! Do you love Late Show with David Letterman? Then you need to check out Hello-Deli.com! It’s the only place to grab officially licensed Late Show merch, courtesy of the legendary Rupert Jee. Whether you want a classic Late Show mug or a t-shirt to prove your fandom, Hello Deli has you covered! HELP US GROW! If you enjoy The Letterman Podcast, do us a solid—like, share, subscribe, and leave a positive comment! It helps more than you know, and Mike’s self-esteem is directly tied to your engagement. Don’t let him down.

This episode features the return of Johnny Mac, host of the Daily Comedy News podcast!Johnny and Mike just had to connect this week to break down some huge moments in the world of comedy—especially those involving David Letterman.For the first time in decades, Letterman made a surprise appearance on The Tonight Show, an event sparked by Paul Shaffer & The World’s Most Dangerous Band taking over house band duties while The Roots prepped for SNL 50.Johnny and Mike react to the reunion, fantasize about a full-fledged Letterman reunion show, discuss Conan O’Brien hosting the Oscars, and much more!And of course, our show is proudly sponsored by Hello-Deli.com—your only source for official Late Show with David Letterman merchandise. Support the legendary Rupert Jee!If you enjoy the show, we humbly (and desperately) ask you to like, share, subscribe, and leave a positive comment. It costs nothing, takes seconds, and helps us not feel like we’re screaming into the void.

This episode features Greg Burmeister, who served as a Late Show with David Letterman page during the final stretch of the show’s legendary run. Greg shares with Mike how he made the leap from Minnesota to New York as a musician, only to land his first gig in the city as a page for Late Show. The two bond over their love of music as Greg recalls some of the incredible bands he saw and interacted with during his time working at the Ed Sullivan Theater. He also shares stories about his surprise run-in with Ryan Reynolds on his very first day, the time he saw Conan O’Brien walk past the Late Show marquee, and many more behind-the-scenes memories. Greg is also the co-host of the podcast Talking Schmidt alongside fellow former page (and Letterman Podcast alum) Eric Schmidt. Big shoutout to our sponsor, Hello-Deli.com — the only place to get licensed Late Show with David Letterman merchandise, run by the legendary Rupert Jee! And if you enjoy the show, please like, share, and subscribe! Or don’t… but if you don’t, we’ll assume you hate joy. #DavidLetterman #LateShow #LateNight #LettermanPodcast #GregBurmeister #TalkingSchmidt #EricSchmidt #EdSullivanTheater #Music #NYC #HelloDeli #RupertJee

This episode features the return of one of our first Friends of the Show, J Ryan! Best known on social media as @PorscheLife111, J is the host of Late Night Playset, which can be found on YouTube. After catching up on how things are in LA following the devastating fires a few weeks ago, J and Mike dive into a long-overdue conversation. They discuss J’s 2.5-month road trip across America, his recent visit to Jay Leno’s garage, and reflect on their history—including the origins of this very show. Stop right there! Have you visited Hello-Deli.com yet? It’s the only place to get official Late Show with David Letterman merch, run by the legendary Rupert Jee himself! We know asking for likes, shares, and subscriptions is as cliché as a Top 10 List… but here we are, doing it anyway! If you enjoy what we do, please help spread the word—it really makes a difference!

This episode features Alita Ditkowsky and her husband, Mike, who share the fascinating story of how Alita found herself in the national spotlight and on Late Show with David Letterman! In 2005, Alita was involved in a high-profile class action lawsuit investigation, which led to several meetings with the highest-ranking officials in the United States, including multiple interactions with President George W. Bush. During one such event, footage of Alita speaking with the president on stage surfaced, creating the opportunity for comedy gold on Late Show. Alita and Mike join The Letterman Podcast to share the amazing series of events that led to these moments, their reactions to being part of Late Show comedy bits, and the joy and laughter it has brought them ever since. Our sponsor: Be sure to check out Hello-Deli.com for officially licensed Late Show with David Letterman merchandise, courtesy of the legendary Rupert Jee! Please Like, Share, and Subscribe: If you’re enjoying The Letterman Podcast, let us know by liking, sharing, and subscribing! Your support keeps the lights on… though Mike’s humor certainly doesn’t!

This episode features Eric Schmidt, who worked as a page and audience coordinator during one of the most entertaining eras of Late Show with David Letterman from 2009 to 2011. Now a stand-up comedian and host of the podcast Talking Schmidt, Eric reflects on his time at the Ed Sullivan Theater with humor and gratitude. Eric and Mike dive into behind-the-scenes stories of Late Show, including the unforgettable music acts Eric witnessed, what it was like to be at the show during Conan’s Tonight Show departure, and his interactions with Dave during those fascinating years. He shares the lasting friendships he made and how his time at Late Show shaped his career and perspective. Visit Hello-Deli.com: Rupert Jee’s Hello Deli is the home of licensed Late Show with David Letterman merchandise. Stop by the website or, if you’re in NYC, pop in and tell Rupert Mike sent you. (He might even smile!) Help spread the word! If you enjoy The Letterman Podcast, please like, share, subscribe, and leave a positive comment. It helps more than you know. Plus, we’ll use the validation to pretend we’re as cool as Eric Schmidt. Hashtags: #TheLettermanPodcast #DavidLetterman #EricSchmidt #LateShow #LateNightTV #TalkingSchmidt #ComedyPodcast #BehindTheScenes #LateShowPages #StandUpComedy #HelloDeli

Episode 160: Andrew L. Buss – The Oral Historian Extraordinaire This week’s guest is Andrew L. Buss, a prolific writer and oral historian who has meticulously documented some of pop culture’s most iconic projects, including The Jerk, Scott Pilgrim vs. The World, High Fidelity, Freaks and Geeks, Clerks: The Animated Series, and more. As an assistant, collaborator, and protégé of the late Bill Zehme, Andrew has written for Consequence of Sound, Vulture, Vanity Fair, and LateNighter.com. He is also recognized as an Andy Kaufman historian. In this lively episode, Andrew and Mike dive deep into the art of storytelling and the nuanced history of late-night television. They focus on Late Bloomer, Andrew’s oral history for Vanity Fair chronicling Conan O’Brien’s succession of David Letterman as the host of Late Night and the extraordinary year that followed. With interviews from all the main players—including David Letterman himself—this piece offers a fascinating perspective on the transition and legacy of late-night television. Have you visited Hello-Deli.com lately? The only place in the world to grab officially licensed Late Show with David Letterman merchandise, brought to you by the one and only Rupert Jee. Check it out—you’ll thank us later. Support the Show! If you enjoyed this episode, please like, share, and subscribe. Leave us a positive comment or two—Mike’s self-esteem is directly linked to your feedback!