Don't Be Alone with Jay Kogen

Comedian Chloe Radcliffe gave up Target corporate for comedy club and has zero patience for people who can't say the word "birthmark" out loud. AND SOMEHOW managed to sell a movie before she really knew how to write one.

Jay sits down with stand-up comedian, screenwriter, and actress Chloe Radcliffe for a funny, candid conversation about what it takes to make it in comedy, why being an outsider might actually be an advantage, and learning to own the thing everyone else notices about you first.

Chloe talks about growing up with a prominent birthmark and how years of dealing with other people's reactions helped shape both her perspective and her comedy. She and Jay dig into why so many comedians seem to come from the outside looking in — and how developing a sense of humor can become both a defense mechanism and eventually a career.

She also tells the wild story of accidentally selling a movie to Columbia/Sony off a verbal pitch before she really understood screenwriting. Suddenly faced with actually writing the thing, Chloe headed to the library, started reading screenplays and screenwriting books, and eventually found inspiration in scripts ranging from Groundhog Day to Jurassic Park.

Chloe also opens up about the less funny side of the comedy world: bad auditions, bombing onstage, audiences that aren't always receptive to women, and an uncomfortable encounter with a male headliner that illustrates the calculations women — and other outsiders — sometimes have to make when power dynamics are stacked against them.

Plus, Chloe explains how ten years of competitive speech and debate quietly trained her for stand-up, why getting laid off from Target may have been one of the best things that happened to her career, what writing for The Tonight Show Starring Jimmy Fallon taught her, and why she's determined to star in her own story rather than watch somebody else play "Chloe."

And somehow Jay and Chloe still find time for narcissism, hardcore crochet, shitty pop-country, Coldplay, and the possibility that maybe some people really are just boring.

It’s comedy-industry war stories, sharp cultural commentary, and two funny people figuring out why anyone would willingly choose a career in show business.Subscribe to Don't Be Alone with Jay Kogen for more conversations with writers, comedians, actors, creators, and thought leaders exploring life, creativity, politics, and the human experience. Website: https://www.dontbealonewjk.com/ Instagram: https://www.instagram.com/dontbealonewithjaykogen/https://www.instagram.com/jaykogen/ Tiktok: https://www.tiktok.com/@dont.be.alone.wit

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Political arguments are everywhere. Productive political conversations? Not so much.

Jay sits down with writer, poet, and political analyst Robert Arnold, author of Defiance Until Death, to talk about why America has become obsessed with winning arguments instead of actually solving problems—and why humiliating the other side probably isn’t changing anyone’s mind.

Robert talks about growing up in rural Arkansas, why he thinks he can reach people across the political divide, the role of faith and identity in American politics, and what it actually takes to have a conversation with someone who completely disagrees with you.

Along the way, Robert attempts something considerably more difficult: explaining all of this to Jay.

They also get into rural America, MAGA, political burnout, money in politics, why local elections matter more than most people realize, and whether there’s still a way for Americans to disagree without treating every conversation like a fight to the death.

Follow Robert Arnold and check out Defiance Until Death wherever books are sold.

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David Kissinger grew up swimming in Nixon's pool, getting bad-mouthed by classmates over his dad's Nobel Prize, and hanging out with people history books call monsters — and he calls uncles. Jay sits down with David Kissinger — son of Henry Kissinger, TV exec behind The Office, Battlestar Galactica, and Netflix's The Beast in Me — for a conversation that swings from Watergate to Ted Danson's phone number to the time Paul McCartney pulled out a harmonica just for him. David tells the story of the president calling his childhood neighbors "sons of bitches" (in front of a 10-year-old), explains how he squandered millions of dollars developing shows before finally getting one right, and gets brutally honest about the show he still thinks was robbed of its shot. Plus: why AI can't write a joke to save its life, what Barry Diller taught him about being a good editor, and how a 6:20am hiking group became his weekly dose of joy. It's part Hollywood war stories, part front-row seat to American political history, and part two old friends just riffing. Also: listener mail about firing a friend without losing her, and a hard stance on marzipan.

Bio:  David Kissinger has spent decades helping decide what America watches on TV — and he's the son of one of the most consequential (and controversial) diplomats in modern history, so he's had a front-row seat to two very different kinds of power. Professionally, Kissinger cut his teeth as a journalist, writing for outlets including Rolling Stone and Esquire, before crossing over into the entertainment industry. He rose through television development at Disney's Touchstone Television, where he helped oversee hits like Home Improvement and Boy Meets World, then went on to run NBC Universal Television Studio, where his fingerprints are on shows including The Office, House, Monk, and Battlestar Galactica. Since 2005, he's served as President of Conaco, Conan O'Brien's production company — proof that after years of corporate TV, he still knows how to have fun.

His father was Henry Kissinger, the former U.S. Secretary of State, National Security Advisor, and Nobel Peace Prize winner. Growing up with that surname meant David spent his childhood somewhere between political history and normal life, which may explain why he's spent his adult life gravitating toward comedy.  Kissinger is married to Alexandra Kissinger, who worked directly with Jim Henson and has helped carry forward the Henson legacy. Outside of work, he's an avid music fan and enjoys hiking and not answering Jay’s texts. 

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Jonathan Shapiro spent years as a successful attorney, working for the Justice Department and prosecuting organized crime. Then he met Jay Kogen — and somehow ended up writing television.

Jonathan joins Jay for a funny and surprisingly personal conversation about leaving the law behind and building a 26-year career writing some of television’s biggest legal dramas, including The Practice, Goliath, The Blacklist, Mr. Mercedes, and The Undoing.

They talk about the strange rules — or complete lack of rules — in show business, why great scripts never get made, what real courtroom experience taught Jonathan about writing television lawyers, and how a chance encounter with Jay helped convince him that maybe life didn’t always have to be vegetables when you could skip straight to dessert.

But the conversation goes deeper than their careers. Jonathan opens up about getting older, losing people he loves, his journey to sobriety, using humor to keep people at a distance, and why genuine connection has become more important to him with age.

It’s a conversation about law, writing, failure, friendship, mortality, and what happens when you finally admit: “Yeah… I’m a writer.”Subscribe to Don't Be Alone with Jay Kogen for more conversations with writers, comedians, actors, creators, and thought leaders exploring life, creativity, politics, and the human experience.

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What happens when two veteran comedy writers start questioning everything they were taught about writing?

Jay sits down with Bill Martin and Mike Schiff, the longtime writing partners behind shows including 3rd Rock from the Sun, In Living Color, Grounded for Life, and The Neighborhood, for a funny and candid conversation about what makes comedy work — and why some of the oldest writing advice might be worth ignoring.

They talk about the decline of the traditional sitcom, why younger audiences will binge hundreds of old episodes but struggle to connect with new comedies, surviving the chaos of In Living Color, taking over The Neighborhood, navigating changing writers' rooms, working with stars like Cedric the Entertainer and John Lithgow, and the strange pressure on writers to constantly “write their truth.”

After decades of writing together, Bill and Mike also explain how their creative partnership survived every argument imaginable — and why sometimes the best thing a writer can do is stop writing what they know.

It’s a conversation about comedy, friendship, changing television, and figuring out how to stay funny when the business around you keeps changing.

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Michael J. Weithorn knows a thing or two about making television work — and about what happens when it doesn’t.

The creator of The King of Queens joins Jay Kogen to talk about the years of trial, error, difficult actors, canceled shows, and hard-earned lessons that eventually led to one of television’s most successful sitcoms.

Michael shares how Jerry Stiller initially turned down The King of Queens, what it was like having Charlie Kaufman in the Ned and Stacey writers’ room, recognizing Bryan Cranston’s talent long before Breaking Bad, and what he learned about running a television show from Family Ties creator Gary David Goldberg.

They also get into the strange reality of creative success: after you finally make the hit show, are you allowed to stop trying? Jay and Michael compare The Simpsons and The King of Queens, talk about why writers keep creating long after they have something to rest their laurels on, and wonder whether any of it ever actually feels like enough.

Plus, Michael discusses directing Kevin Bacon and Kyra Sedgwick in his new film The Best You Can, the disappearing world of old-school TV writers’ rooms, and why comedy writers may simply be incapable of leaving a perfectly good dramatic moment alone.

Michael J. Weithorn is an award-winning writer, producer, director, and creator of The King of Queens, with credits including Family Ties, Cheers, Ned and Stacey, True Colors, and The Wonder Years.

Bio: Michael J. Weithorn is an award-winning writer, producer, and director with over four decades of experience in Hollywood television and film. He is best known as the creator and executive producer of The King of Queens, the beloved CBS sitcom that ran for nine seasons and 207 episodes, and has brought numerous other series to life across major networks, including Ned and Stacey, True Colors, and Weird Loners. Earlier in his career, he honed his craft as a producer and story editor on Family Ties and earned a WGA Award for his Cheers script and an Emmy nomination for The Wonder Years. His feature work includes A Little Help (2011) and the upcoming The Best You Can (2025), starring Kevin Bacon, Kyra Sedgwick, Judd Hirsch, and Ray Romano.  Beyond his creative work, Weithorn is a dedicated educator, teaching screenwriting as an adjunct professor at Columbia University's MFA program and UC Santa Barbara, while also leading comedy writing workshops for organizations including the Ghetto Film School and Inside Out Writers, an L.A.-based anti-recidivism program.

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Comedy historian and author Kliph Nesteroff joins Jay to answer one of life's great mysteries: Why are Canadians so damn funny?

From Jim Carrey and Norm Macdonald to Kids in the Hall, Nathan Fielder, SCTV, Michael J. Fox, and countless others, Canada has produced an absurd amount of comedy talent. Kliph has a theory about why — and it might have something to do with being an outsider looking in on America.

Kliph also tells Jay about growing up in rural Canada, obsessing over comedy and The Simpsons, becoming “California sober” before ever moving to California, and the legendary high school election where he roasted his teachers in front of the entire school, won the presidency 398–2… and promptly got kicked out.

They also dig into the strange history of Canadian television, why some brilliant Canadian comedians never become famous in America, what actually makes something funny, and why Southern California apparently doesn't count as moving to the United States.

Kliph's new book, Sorry, We're Funny: How Canada Became a Comedy Powerhouse, explores how a country once dismissed as humorless became responsible for some of the funniest people in entertainment.

And after nearly an hour of discussing what makes Canadians funny, absolutely no progress is made toward explaining Jay.

Bio: Kliph Nesteroff is the author of four books about comedy: The Comedians, We Had a Little Real Estate Problem, Outrageous and the forthcoming Sorry, We're Funny: How Canada Became a Comedy Powerhouse. He often appears in his capacity as comedy historian on CNN, HBO and Vice and has worked on projects with Judd Apatow, Albert Brooks and the late Rob Reiner. Born in Castlegar, British Columbia, he grew up watching Wayne and Shuster and the Kids in the Hall on CBC.

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M*A*S*H and Laugh-In writer/producer Allan Katz and Groundlings pioneer Phyllis Katz join Jay Kogen to compare the wildly different paths that took two siblings from the same Chicago household into legendary careers in comedy.

Allan's story sounds almost made up. While working in advertising, his work on Screaming Yellow Zonkers caught the attention of Laugh-In producer George Schlatter — who tracked him down and offered him a job. Allan, having no idea who was calling, hung up on him. More than once.

Phyllis's career began with an equally unlikely encounter. After walking into Second City and asking Joe Flaherty if they bought song parodies, he handed her a flyer for their workshops. As Phyllis remembers it: "My life changed forever."

From growing up with a former vaudeville hoofer for a father, to Laugh-In, M*A*S*H, Second City and The Groundlings, Allan and Phyllis talk about where funny actually comes from, surviving rejection, taking creative risks, finding your way into "the zone," and why sometimes an entire career can turn on one completely unexpected moment.

And beneath all the comedy is something even more personal: the strange bond between siblings who share a lifetime of memories, inside jokes, and a language nobody else quite understands.

So... is comedy genetic?

Jay tries to find out.Subscribe to Don't Be Alone with Jay Kogen for more conversations with writers, comedians, actors, creators, and thought leaders exploring life, creativity, politics, and the human experience.

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When does pushing for what you want become pushing too far?

Jay sits down with comedian, writer, performer, and Valley Heat creator Christian Duguay for a conversation about boundaries, bad decisions, creative confidence, and knowing when to make the call and when to leave something alone.

At the center of Valley Heat is Doug Duguay, a fictional character who keeps finding himself in increasingly ridiculous situations. He suspects his pool guy is dealing drugs. He worries about his wife's yoga instructor. He obsesses over a mysterious car parked outside his house. And somehow, almost every questionable decision Doug makes seems perfectly reasonable…at least to Doug.

Christian admits there's more of himself in Doug than you might expect.

That leads Jay and Christian into a bigger question: How do you know when you're being persistent and when you're just being pushy?

Jay has always believed in making the phone call, asking for the opportunity, and fighting for what you want—even if that occasionally means annoying someone. Christian has traditionally been more cautious. He didn't even show Valley Heat to his manager until he'd made ten episodes and knew he believed in it. 

But by the end of their conversation, the two find some common ground: sometimes the phone call you're afraid to make is exactly the one you should make. As Christian puts it, most of us have needed someone to give us advice, open a door, or push us in the right direction—and sometimes getting what you want requires having the nerve to ask. 

They also talk about Christian's years at The Groundlings, abandoning stand-up, struggling with creative confidence, making music, building the bizarre world of Valley Heat, and why sometimes the best thing a creative person can do is make something they like and put it into the world.

So where's the line?

When should you push and when should you back off?

Follow Christian Duguay:

Socials: https://www.instagram.com/csduguay/ 

Podcast: https://valleyheatpodcast.com/ 

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From Arrested Development to insubordinate rebels: John Levenstein tells all.

Long before podcasting was cool, John Levenstein (Arrested Development, Kroll Show) was already doing it — mostly because he had no idea what he was signing up for. In this episode, the veteran writer/showrunner gets refreshingly honest about what actually makes a comedy writers' room work.

His controversial take? Not everyone needs to agree. In fact, forcing consensus on a writing staff is its own kind of bullying — the showrunner's job is to make the call, not manufacture harmony. John also makes the case for "wasted time" as secret sauce: some of the best jokes in Arrested Development came from writers chasing pointless tangents that turned into five seconds of pure gold. Sometimes the grinding, chaotic, deadline-crushing process is the recipe.

Then things get personal. John opens up about growing up without a male role model, why authority has always struck him as absurd, and how that turned him into a lifelong "insubordinate rebel" — one who somehow also became one of the most trusted, well-liked insiders in the business. He's the guy everyone wants to text, the friend who asks for nothing, and — surprisingly — a guy singing lessons made genuinely happy.

Equal parts industry insight and unexpectedly moving personal story.

Don't miss it.Follow John Levenstein: Socials: https://www.instagram.com/saltinwound/

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