To be human is to fail – period. And not just to fail once, but to fail a lot. As the author Samuel Beckett said: “Fail again. Fail better.” This saying means a lot to me and my family – so much so that my daughter got a tattoo of it. Why are we, and so many others, so deeply concerned by failure? And if it’s something we all do so often, why are we so afraid of it – especially those of us here in win-at-all-costs America? In this podcast, I sit down with successful, thoughtful people like Ben Stiller, Bette Midler, Sean Penn and more to talk about failure – or what they labeled “failure,” but what was really an unparalleled opportunity for growth and revelation. I even want to delve into my own hardest moments, when I wrestled with setbacks, shame, and fear. We’ll still fail again. And again. But maybe if we fail better, we’ll feel better -- and maybe if we can all laugh together in failure, that's a start.
Episodes
Fail Again: The Family Business with Robert Downey Jr.Mar 31, 20263542This episode originally aired July 22, 2025
The spotlight has certainly taken its toll on Robert Downey Jr. over the years. But much like his beloved MCU character Tony Stark, there's an undeniably powerful force inside Robert that keeps him pushing forward. When we sat down over iced coffees, we found ourselves unpacking the fraught relationship Robert had with his father — the experimental, cou
Fail Again: Chris Carter Wants You To BelieveMar 24, 20263988This episode originally aired June 3, 2025
The X-Files was always about turning something mysterious and untraceable into something known — so what better time to capture the elusive podcast interview on camera? That’s right: Fail Better is now on video, and we’re kicking off this new chapter with the one and only Chris Carter, the creator of The X-Files. And he came prepared, alien embryo and al
Fail Again: Aimee Mann Is In My PantheonMar 17, 20263480This episode originally aired November 19, 2024
It was a real magic moment to connect with Aimee Mann, a musician I’ve listened to for decades. She indulges my curiosities about lyric choices and instrumental training, and I learn how much goes on behind the scenes of an Aimee Mann production. We talk about the traumas of her past, which hardships do and do not influence her work, and why there f
Fail Again: Griffin Dunne — An Actor Builds CharacterMar 10, 20263056This episode originally aired July 30, 2024
The nephew of Joan Didion and John Gregory Dunne, and son of Dominick Dunne, becoming anything other than a writer feels almost sacrilegious. Yet Griffin Dunne only recently became an author, publishing his family memoir “The Friday Afternoon Club” after spending decades in other fruitful and wide ranging creative pursuits. The actor and producer, known
Fail Again: Failure, Freedom, and ‘Friends’ with Maggie WheelerMar 3, 20264085This episode originally aired February 11, 2025
While Maggie Wheeler is known by millions as the iconic Janice on ‘Friends’, she has been my real-life friend for even longer. Back in the late 80s, we made our film debuts together, playing former lovers, which is a distinction we shared in real life, even at that time. And we’ve stayed close even as our lives and careers went off in the various wa
Fail Again: Kumail Nanjiani’s New AmbitionFeb 24, 20263319This episode originally aired August 13, 2024
When I first met Kumail Nanjiani, we were on set on the X-Files, chasing down the shape-shifting Were-Monster. Since then, I’ve seen Kumail undergo his own transformation — into a leading man and big-screen superhero, playing memorable characters with depth, heart and humor. Only, he doesn’t always see it that way. We chat about his love of the X-File
Fail Again: Kathleen Hanna’s Music is Her MessageFeb 17, 20263082This episode originally aired August 16, 2024
Being “indie famous” is complicated, and Kathleen Hanna isn’t here to water it down. Her career making feminist punk music — most notably in the band Bikini Kill — meant she was attacked for her activism by some and objectified as a symbol by others. But Kathleen and her bandmates continued to fight for respect and wrangle messy topics into punchy son
Fail Again: The Buoyancy of Rob LoweFeb 10, 20263735This episode originally aired January 14, 2025
Throughout his long and varied career, Rob Lowe has become an expert at reinventing himself. He left behind his bad-boy image from iconic 80s movies to work on a clever mix of dramatic and comedic TV roles. But I’ve known Rob for a while, and he’s a very layered individual. We look back at how Rob has pursued his passions and how he and his wife, She
Fail Again: Roads Taken and Not Taken with Jason BegheFeb 3, 20262978This episode originally aired October 15, 2024
I’ve known Jason Beghe for 50 years and counting, ever since we met one fateful day in a high school biology class. I watched as this rambunctious and rebellious kid grew up and carved his own path, never following trends. But when Jason became heavily involved in the Church of Scientology, we drifted apart — and I felt like I’d failed him as a frien
Fail Again: Sean Penn and the Squared-Away IndividualJan 27, 20263530This episode originally aired June 18, 2024
There are few actors left who embody the ethos of old Hollywood. Sean Penn is one of them. We got together at his place for a face-to-face exploration of Sean’s life and career. We discussed how his childhood in Malibu helped him create the iconic Jeff Spicoli, and how his first acting coach still shapes him today. We speak of his friends — Brando, DeNi
Fail Again: Failure Matters with Jaleel WhiteJan 20, 20263488This episode originally aired March 18, 2025
To me, there are few sitcom characters more memorable than Steve Urkel on Family Matters. So getting to talk to the actor Jaleel White — about his approach to acting, his take on Hollywood in the ‘90s and now, and what it’s meant to have a character follow him into adulthood — was as illuminating as I’d expected. As a pillar of show business and an ast
Fail Again: Chris Evert Hates To Lose More Than She Loves To WinJan 13, 20263400This episode originally aired April 22, 2025
After an illustrious tennis career, of course Chris Evert cherishes the wins and broken records. Yet, the sting of defeat is also etched in her memory, marked by days secluded in hotel rooms with the worst missteps replaying in her mind. Life as a high-profile athlete began for Chris as a teenager, and it opened her up to intense scrutiny from tabloids
Fail Again: Failure-ish with Kenya BarrisJan 6, 20263856This episode originally aired February 25, 2025
Kenya Barris, the creator of "Black-ish", knows a thing or two about resilience. Eighteen failed pilots before he finally struck gold? That's dedication — and, as it turns out, a family value. I’d always been drawn to Kenya’s humor and storytelling, but during our conversation it really clicked how much his experience as a father — and, as he openly
Fail Again: A Forensic Analysis with Emily DeschanelDec 30, 20253707This episode originally aired July 8, 2025. My interview with Emily was one of our most popular of 2025, so we’re playing it again to cap off the year.
Emily Deschanel spent over a decade portraying the brilliant and meticulous forensic anthropologist Dr. Temperance Brennan on the hit crime procedural Bones. Yet, what many viewers never knew about was her personal battle behind that confident per
David Duchovny Gets Weird with Pete HolmesDec 23, 20256297While we’re on holiday break, I wanted to share one of my favorite conversations from 2024 — my appearance on Pete Holmes’s podcast, You Made It Weird. Pete and I dive into the big stuff: creativity, aging, family, ego, spirituality, and why trying (and failing) is often the most interesting part of being human. It’s funny, thoughtful, and wonderfully weird in all the best ways.
If you want to h
Fail Again: Catching Up with Gillian AndersonDec 16, 20253980This episode originally aired on November 12, 2024.
Gillian Anderson and I share a connection unlike any other. The Dana Scully to my Fox Mulder, we are the only ones who understand what the other was going through during those X-Files years. But so much was left unsaid — until now. We got a chance to open up about the ways we might have failed one another during that wild ride, and we both exami
John Seabrook’s Family Was the Vegetable Version of ‘Succession’Dec 9, 20252948John Seabrook is a journalist and author best known for his work at The New Yorker magazine. This means he didn’t go into the family business: large-scale industrial agriculture. During their heyday, Seabrook Farms was a household name in frozen vegetables. But an internal power struggle that lasted for generations ultimately tore the family and the business apart. In his latest book, The Spinach
The Many Lives of Peter WellerDec 2, 20253219Sitting across from Dr. Peter Weller — another actor/author/academic like myself — I knew I was in for an engaging conversation. But as Peter explained the shape his life has taken, I saw beyond his vast accomplishments to his deep sense of self-knowledge. Long before he was Robocop, Peter was a masterful jazz trumpet player, idolizing innovators like Miles Davis. Yet, for all Peter’s talent, the
Introducing: Don't Listen To Us with Mandy Patinkin and Kathryn GrodyNov 25, 20253011For the Thanksgiving holiday, who better to hear from than a family who has fought hard for the communication, compromise, and comedy that fuels their daily lives?
Don’t Listen To Us is an advice show for advice skeptics and wisdom lovers, hosted by Mandy Patinkin, his wife Kathryn Grody, and their son Gideon. Legendary actor Mandy (The Princess Bride, Homeland, Criminal Minds) is the consummate
Kyle MacLachlan (Directed by David Lynch)Nov 18, 20253805The actor Kyle MacLachlan readily acknowledges the immense impact that the late director David Lynch had on his life and career. After making his on-screen debut starring in Lynch's sci-fi epic Dune (1984), Kyle expected superstardom — only to see the movie flop commercially. However, the connection he forged with Lynch led to a lifelong friendship and a filmography inhabiting the director's unfor
How Megan McArdle Became a Liberal-tarianNov 11, 20253202As a columnist for the Washington Post, Megan McArdle tackles the most fraught political topics of our time. So why did we spend so much time talking about pie? It turns out, it's all connected. We discuss how the same forces that shape our nation — especially technology — have also shaped our relationship with craft. A self-described "liberal-tarian", Megan has a unique way of articulating both s
Waxing Poetic with Jia Tolentino (Live at Strand)Nov 4, 20252945Back in September, I sat down with powerful writer and past guest Jia Tolentino at the Strand Bookstore in New York City to discuss my first poetry collection, About Time. This book is a poetic autobiography of sorts, gathering moments and fragments from my life. In front of a hometown crowd, Jia and I explore my early inspirations, debate poems versus songs, and I even read a few of our favorite
Failure? Success? Judd Apatow Says Give It 10 Years to DecideOct 28, 20253176Take a walk through Judd Apatow’s office, like I did, and you’ll be reminded of all the successful projects he’s helped create over the years: Anchorman, Bridesmaids, Superbad, The 40-Year-Old Virgin. I joined him there to discuss his new visual memoir, Comedy Nerd: A Lifelong Obsession in Stories and Pictures. As I learn throughout our conversation, Judd’s propulsion to create isn’t to prove that
Fail Again: Ben Stiller Confronts His Parents' LegacyOct 21, 20253252You might remember from way back when this podcast started that my very first guest was Ben Stiller. It was a memorable interview for lots of reasons, including that Ben talked to me about his parents, Jerry Stiller and Anne Meara and the documentary about the two of them he was working on. Well, that film is about to be out in the world. It’s called Stiller & Meara: Nothing Is Lost, and it’s stre
Listen Now: Alive with Steve BurnsOct 14, 20252859Steve Burns was nice enough to join me on the show a few weeks ago, so I wanted to give you all a chance to listen to his new podcast.
There are a thousand podcasts you can listen to; Alive with Steve Burns listens back. Steve Burns is continuing the conversation he began all those years ago. Back then it was letters and numbers and graham crackers. Now it’s death, sex, taxes, and all the big, me
No Scars, No Stories with Charlie Sheen (Live at 92NY)Oct 7, 20253631Charlie Sheen is an actor perhaps known just as well for his off-screen antics as his on-screen performances. In his new memoir, The Book of Sheen, Charlie is finally coming clean on what was going on during his years of hard drugs, public divorces, and on-set disputes that came to define his later career and reputation. These days, humility, gratitude, and sobriety have come to replace his meme-a
Looking Back: Gretchen Rubin Wants to Make You Happy/ishSep 30, 20253249This week we’re revisiting my conversation with the author Gretchen Rubin, since we could probably all use a little more light these days. Gretchen has spent years trying to understand happiness, the ways she can access it herself, and how to bring others in on the wisdom she’s gained.
Gretchen also has a new podcast, Since You Asked, with bestselling author and psychotherapist, Lori Gottlieb. T
How Steve Burns Found His Aliveness AgainSep 23, 20253530Steve Burns is best known for being the host of a beloved 90s children’s show, Blue’s Clues, so I didn’t expect this interview to be about Samuel Beckett. But it turns out that Steve and I share a deep admiration for the writer, as well as a lot of other common ground. Steve went quiet for about two decades after rumors of his death took over the internet, and now he’s back with a podcast (Alive,
Tom Pelphrey Wouldn’t Change a DaySep 16, 20253338A decade ago, the actor Tom Pelphrey couldn’t have imagined the shape his life would take today: a father to a two-year-old daughter, starring in the new HBO series Task alongside Mark Ruffalo, and engaged to actress Kaley Cuoco. He was gripped by alcoholism and dissociation, having spent years working long, demanding days on the soap opera Guiding Light and ignoring his feelings to keep up with t
Gene Simmons: The Demon Loves His MomSep 9, 20253806If Gene Simmons’ hard exterior scared you off, it did its job. As a founding member of the band KISS, Gene has spent decades putting on what he calls a persona, and today it comes off — at least a little. We talk about Gene’s journey, including being raised by a single, adoring mother, the origins of KISS, and why Ozzy Osbourne’s down-to-earth demeanor had such an impact on Gene. The man in the ch
Check It Out: Building a Legacy with Tisha Campbell (Legacy Talk)Sep 2, 20253361Hey, Fail Better listeners — here’s a great show I think you should know about: Legacy Talk, hosted by the Emmy-winning writer, actor, and producer Lena Waithe. It’s a part of the Lemonada network, and it’s kicking off a second season of incredible episodes featuring trailblazing Black artists and makers.
You’re about to hear the first episode of season 2, featuring the actress and singer Tisha C
Amanda Knox’s Story Isn’t OverAug 26, 20254203Amanda Knox was a young student in a foreign country when she was thrust into an international media firestorm, accused — and then ultimately acquitted — of the murder of her roommate. Now an author and public speaker, she’s the executive producer of the new scripted drama “The Twisted Tale of Amanda Knox”, an attempt to finally tell her story on her own terms. She has spent years grappling with t
The Pitfalls of Manhood with Terry RealAug 19, 20253783I should’ve known I was in for a revelatory conversation when I met with the family therapist Terry Real. He pioneered a book on male depression in the ‘90s, and he’s been helping countless people break through mental and relational barriers in the years since. I start the conversation by inquiring about how Terry knew he would be good at this work, and before I know it we’re talking about my moth
An Hour with Melissa Febos About a Year Without SexAug 12, 20253892Memoirists do the generous work of letting us into their lives, and then there are ones like Melissa Febos who also graciously entertain all the new questions their work inspires. Melissa lets me in on the elements of her life and experiences that I’m curious about, from people’s reaction to her job as a dominatrix (as documented in her book Whipsmart) to her year-long trial of celibacy (the focus
Jess Walter Can Hoop (and Write)Aug 5, 20254268I’m coming to you live from Vroman’s Bookstore in Pasadena, California, where I got to sit down with my friend, author Jess Walter. We chatted in front of a packed house (including a few friendly dogs) and now we’re sharing that event with the rest of you. Jess is not only my go-to buddy to text about all things basketball; he’s an accomplished novelist who can skewer the Hollywood elite just as e
Tim Minchin’s Infinite UniversesJul 29, 20253316The musician (-comedian-actor-composer-director-Californication guest star) Tim Minchin is an aspirational figure. He brings an unmatched level of precision and thoughtfulness to conversations, whether he’s discussing word play or the Catholic church. And he extends that scrutiny to his concepts of success and failure, which I welcome. Tim and I sit down to talk about the intricacies of his work,
The Family Business with Robert Downey Jr.Jul 22, 20253542The spotlight has certainly taken its toll on Robert Downey Jr. over the years. But much like his beloved MCU character Tony Stark, there's an undeniably powerful force inside Robert that keeps him pushing forward. When we sat down over iced coffees, we found ourselves unpacking the fraught relationship Robert had with his father — the experimental, countercultural filmmaker Robert Downey Sr. — wh
What Jake Clark Wants You To Know About TraumaJul 15, 20253541Jake Clark is an unexpected hero. As the founder of the Save a Warrior program for veterans and first responders, he helps those suffering from post-traumatic stress uncover the core of their pain, which often stems from trauma that came before combat or violence. His work has led to surprising breakthroughs for many people, mirroring his own journey of self-discovery after years of self-destructi
A Forensic Analysis with Emily DeschanelJul 8, 20253707Emily Deschanel spent over a decade portraying the brilliant and meticulous forensic anthropologist Dr. Temperance Brennan on the hit crime procedural Bones. Yet, what many viewers never knew about was her personal battle behind that confident performance: diagnosed with ADHD and dyslexia at a young age, Emily often struggled to master the intricate anatomical jargon week after week. Pushing throu
Check It Out: The Disappearance of Eric Robinson (Uinta Triangle)Jul 1, 20253892For the Fourth of July holiday, we’re taking you on a getaway of sorts. It’s one that brings you to the beautiful mountains of New Zealand… but is decidedly less relaxing than a summer vacation. Today we’re sharing the first episode of a new podcast called Uinta Triangle, which documents the disappearance of a solo hiker named Eric Robinson. It’s a gripping and multifaceted story about exploration
Truth and Lies with James FreyJun 24, 20253386In his aimless youth, the author James Frey yearned to be the Sex Pistols of literature. Then he learned to be careful what you wish for. His memoir, A Million Little Pieces, shot to the top of bestseller lists, thanks in part to Oprah's endorsement. Then fact-checkers unmasked its fabrications, and James found himself being more of an outcast than he’d planned for. Nearly 20 years later, when the
From “Junkie Doctor” to Addiction Specialist with Dr. Jason GilesJun 17, 20253849Dr. Jason Giles is an addiction specialist and a helper and friend to many, including me. When the rigors of life in the ER became too much to cope with, Jason turned to the very narcotics he was trained to supply to patients as a trauma anesthesiologist. As his successful life disintegrated, he was forced to face his own doubts and delusions, and his journey through them is what made him who he i
AI Should Fear Justine BatemanJun 10, 20253960I’ve known for years that the actor and filmmaker Justine Bateman had prescient thoughts about art and society. But now, we need her (and her complementary background in computer science) more than ever. Far-removed from her teen stardom on Family Ties, Justine and I talk about how artificial intelligence threatens the existence of movies, books, and even our creative souls. I knew there was somet
Chris Carter Wants You To BelieveJun 3, 20253988The X-Files was always about turning something mysterious and untraceable into something known — so what better time to capture the elusive podcast interview on camera? That’s right: Fail Better is now on video, and we’re kicking off this new chapter with the one and only Chris Carter, the creator of The X-Files. And he came prepared, alien embryo and all. There’s so much to discuss about the show
Check it Out: Ira Glass on Three Decades of ‘This American Life’ MagicMay 27, 20255190Hey, everyone. Today I wanted to share a special conversation from another Lemonada show: Talk Easy with Sam Fragoso.
For those who aren’t already familiar with this great podcast, the show started all the way back in 2016 and airs every Sunday. The episode you’re about to hear is a recent one. It’s a great talk between Sam and the broadcast legend Ira Glass, from May 2025.
Thirty years. Over 8
Not Reading the Comments with Maureen DowdMay 20, 20253088The journalist Maureen Dowd has many notches in her belt, from feats like winning a Pulitzer Prize and writing pivotal profiles on some of the world’s most powerful people. She shone light on Elon Musk before DOGE and Uma Thurman’s emotional struggle with Quentin Tarantino, all of which is captured in her latest book, Notorious. Even for her, though, the process of writing remains fickle. Both Mau
Remembering to Forget with Lewis HydeMay 13, 20253024Lewis Hyde is one of those contemporary authors whose work I think about a lot. He’s spent years reflecting on and writing about topics of great interest to me, like forgetting and forgiveness, but the true trademark of his work is how he processes concepts and describes them. He approaches his work like chasing a butterfly (a lifelong hobby of his), following the dips and curves of an idea until
Playing God with Jonathan RoumieMay 6, 20253755Jonathan Roumie is a genuinely charismatic individual, which is understandable given his acclaimed portrayal of Jesus in the immensely popular Christian historical drama The Chosen. However, long before embodying arguably the most significant main character in history, Jonathan was, to borrow the familiar lyric, “just a slob like one of us.” He spent time drumming in bands, working as a location s
Looking Back: One Year of Fail BetterApr 29, 20253738It’s finally here: the one-year anniversary of the launch of Fail Better. This moment brought out a lot of feelings and jokes about what it’s meant to make this show and have the conversations I’ve had, and you get to hear me talk about that here. Then I play one of my favorite interviews I’ve had, with the one and only Rosie O’Donnell, who enthusiastically joined me in challenging the standard fo
Chris Evert Hates To Lose More Than She Loves To WinApr 22, 20253400After an illustrious tennis career, of course Chris Evert cherishes the wins and broken records. Yet, the sting of defeat is also etched in her memory, marked by days secluded in hotel rooms with the worst missteps replaying in her mind. Life as a high-profile athlete began for Chris as a teenager, and it opened her up to intense scrutiny from tabloids. But it also brought unprecedented levels of
The Grit and Grind of Steve LukatherApr 15, 20253105As a founding member of the band Toto, Steve Lukather is well aware of the song you probably know him for. But Steve, known to most as “Luke”, has plenty of other claims to fame. Luke is a seriously talented guitarist and writer with more than a dozen albums to his name from Toto alone, not to mention an almost infinite number of credits and Grammys from his session work with stars like Paul McCar
EXCLUSIVE PEEK: Reflections on Alec Baldwin, Kenya Barris, and moreApr 8, 20252712This week, we’re offering another peek at the kinds of things you might hear in Lemonada Premium. At the end of each regular episode, there’s a snippet of my thoughts about the conversation, but those are just snippets. My post-mortems are much longer than that, and we publish the full versions exclusively for Lemonada Premium subscribers. Today, we’ve pulled a few for you to hear from some of my
Graydon Carter and The Editor’s EyeApr 1, 20253461Graydon Carter, the editor whose two decades at the helm of Vanity Fair transformed the publication, sure knows how to curate. He made the magazine into the cultural touchstone it is today (think: the much-photographed Vanity Fair Oscars Party, the viral celebrity lie-detector tests), though not without trial, error, and lots of nerves. He and I talk about his long tenure, the pitfalls of a projec
25 Years Later and Bree Sharp Is Still Asking Why Won’t I Love HerMar 25, 20252936In 1999, the musician Bree Sharp released a single titled “David Duchovny,” off her debut album, A Cheap and Evil Girl. Despite it being the early days of the internet, the song — with its refrain “David Duchovny, why won’t you love me?” — found its way to me, as did the surprise music video that a bunch of people came together to make for our X Files Christmas party. In the time since, Bree and I
Failure Matters with Jaleel WhiteMar 18, 20253488To me, there are few sitcom characters more memorable than Steve Urkel on Family Matters. So getting to talk to the actor Jaleel White — about his approach to acting, his take on Hollywood in the ‘90s and now, and what it’s meant to have a character follow him into adulthood — was as illuminating as I’d expected. As a pillar of show business and an astute observer of it, Jaleel is someone whose pe
Check it Out: “Use a Messy Closet, a 3-Hour Rule for Difficult People & Renowned Judy Blume on Reading”Mar 11, 20252078This week I’m excited to share an episode of the podcast Happier, hosted by past guest Gretchen Rubin.
Gretchen’s podcast, on the Lemonada Media network, explores how we can live a more fulfilling life. In this episode, Gretchen addresses the common feeling of not having enough time to cross all the things off your to-do list, and she offers a useful and guilt-free strategy for sorting through pr
Peter Singer Wants to Save Animals… and Humans, TooMar 4, 20253519Peter Singer has a pretty simple mission: minimize the suffering of all living creatures. But a seemingly straightforward objective can lead to some surprisingly thorny questions. As a philosopher and professor, he’s spent decades pondering the ethical dilemmas that come with living in the modern world. His books have ignited movements — from animal rights to wealth equality — but his deeply perso
Failure-ish with Kenya BarrisFeb 25, 20253856Kenya Barris, the creator of "Black-ish", knows a thing or two about resilience. Eighteen failed pilots before he finally struck gold? That's dedication — and, as it turns out, a family value. I’d always been drawn to Kenya’s humor and storytelling, but during our conversation it really clicked how much his experience as a father — and, as he openly shared, navigating divorce — informs his work. W
Kara Swisher Is So Much More Than the World’s ‘Musk-splainer’Feb 18, 20254834As someone who knows tech giants like Elon Musk more deeply than most reporters, Kara Swisher doesn’t have a ton of patience for them. But that doesn’t mean she doesn’t have empathy. Reflecting at this pivotal moment, she’s stripping away the facades of these powerful men to reveal their true characters (typically, cringeworthy pretenders). She and I share an energetic back-and-forth about what ma
Failure, Freedom, and ‘Friends’ with Maggie WheelerFeb 11, 20254085While Maggie Wheeler is known by millions as the iconic Janice on ‘Friends’, she has been my real-life friend for even longer. Back in the late 80s, we made our film debuts together, playing former lovers, which is a distinction we shared in real life, even at that time. And we’ve stayed close even as our lives and careers went off in the various ways lives and careers go. She and I talk about thi
EXCLUSIVE PEEK: Reflections on Gillian Anderson, Rosie O’Donnell, and moreFeb 4, 20252382This week, I’ve got some more behind-the-scenes content for you. As you know, at the end of each episode you hear a little snippet of my thoughts from after the interview wrapped up. What you might not know is that I share the full version of those thoughts with our Lemonada Premium subscribers each week. Today, I’m giving you all a chance to hear what those are like. And I figured, why not give y
The Humor of Being Human with Costica BradatanJan 28, 20253326The author of In Praise of Failure, Costica Bradatan, joins me from Romania to share his wisdom on all things lack and loss. We talk about the true meaning of humility, the benefits of clumsiness, and just how broken democracy is — and has been — across time and place. Plus, we discuss quite possibly the biggest failure of all, the one none of us can avoid: death. I got to indulge my latent philos
Looking Back: Mary Trump Knows We’re At a CrossroadsJan 21, 20253737As the presidential administration turns over, it feels like an important time to revisit the family dynamics that brought about Donald Trump. His niece, Mary Trump, has long lived in the shadow of her family’s name. And as she writes in her memoir, Who Could Ever Love You, the darkness of that shadow affected generations of Trump children long before it took hold of the world. We talk about her g
The Buoyancy of Rob LoweJan 14, 20253735Throughout his long and varied career, Rob Lowe has become an expert at reinventing himself. He left behind his bad-boy image from iconic 80s movies to work on a clever mix of dramatic and comedic TV roles. But I’ve known Rob for a while, and he’s a very layered individual. We look back at how Rob has pursued his passions and how he and his wife, Sheryl, have used practical techniques to keep thei
Gretchen Rubin Wants to Make You Happy/ishJan 7, 20253249I’m no self-help guru. And while I don’t think Gretchen Rubin would identify as one, she’s dedicated her work to figuring out just what the hell it means to live a full life. As a writer and former lawyer, Gretchen has spent years trying to understand happiness, the ways she can access it herself, and how to bring others in on the wisdom she’s gained. We talk action-led thoughts and aphorisms — an
Looking Back: Ben Stiller and the Curse of the SequelDec 31, 20243215As 2024 comes to a close, I’m feeling grateful for the conversations this show has allowed me to have, including the one that started it all. In honor of the growth (and growing pains) since the show launched earlier this year, I’m sharing the first episode of Fail Better, featuring the one and only Ben Stiller. It was my first-ever interview, and it unlocked something that I’ve continued to explo
Alec Baldwin Might Need to Write Another MemoirDec 17, 20243710The actor Alec Baldwin has spent a lot of time at life’s intersections. He came of age with challenging circumstances on one side and larger-than-life role models on the other. And when you look at how he works or how he parents (he’s now a father of eight), you’ll see that the duality has stuck around. He and I talk about how it’s possible to feel regret and gratitude in one breath, the specific
Dr. Vivek Murthy Wants to Help Us HealDec 10, 20243510As the United States Surgeon General, Dr. Vivek Murthy is dedicated to keeping the public healthy and safe. But these days, that involves much more than just cigarette warning labels. Dr. Murthy knows health should be looked at holistically, and he’s used his position to spotlight topics you might not think of as health crises, like gun violence, loneliness, and social media. We discuss his values
Socialism, Anarchy, and Pixar Movies with Jack HalberstamDec 3, 20243165Jack Halberstam, the author of The Queer Art of Failure, is someone I’ve wanted to talk to since I first started this podcast. As a professor and scholar, Jack has dedicated his career to dissecting the often-radical undertones of popular cultural media. Together, we look at how animated kids’ movies like Shrek, Finding Nemo, and Chicken Run offer critiques of a system that fails so many of us. We
Aimee Mann Is In My PantheonNov 19, 20243480It was a real magic moment to connect with Aimee Mann, a musician I’ve listened to for decades. She indulges my curiosities about lyric choices and instrumental training, and I learn how much goes on behind the scenes of an Aimee Mann production. We talk about the traumas of her past, which hardships do and do not influence her work, and why there feels like a creative imperative to turn pain into
Catching Up with Gillian AndersonNov 12, 20243980Gillian Anderson and I share a connection unlike any other. The Dana Scully to my Fox Mulder, we are the only ones who understand what the other was going through during those X-Files years. But so much was left unsaid — until now. We got a chance to open up about the ways we might have failed one another during that wild ride, and we both examine the ways we’ve grown since. Gillian also caught me
Jia Tolentino Battles The InternetOct 29, 20242820Jia Tolentino has the internet to thank for some of her biggest successes. In the 2000s, it offered her connections beyond her strict religious community and gave her a place to share her writing with her millennial peers. Her “online” insights carved out a niche at The New Yorker, and her 2019 essay collection, Trick Mirror: Reflections on Self-Delusion, made a big splash with readers who felt si
The ElectionOct 28, 2024331I go on the record with my opinions on the election. Not surprisingly, given this podcast, I find some major connections to failure.
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Bluffing with Nate SilverOct 22, 20243130Nate Silver is a risk taker. On top of boldly and publicly forecasting elections as part of his website FiveThirtyEight, he’s a regular poker player, and in just one season of basketball, he bet nearly 2 million dollars on games. He still doesn’t have the foolproof winning formula figured out – even though that’s the ultimate forecaster’s promise – but that doesn’t mean I wouldn’t bet on him, or a
Roads Taken and Not Taken with Jason BegheOct 15, 20242978I’ve known Jason Beghe for 50 years and counting, ever since we met one fateful day in a high school biology class. I watched as this rambunctious and rebellious kid grew up and carved his own path, never following trends. But when Jason became heavily involved in the Church of Scientology, we drifted apart — and I felt like I’d failed him as a friend. For the first time, we unpack what went on be
What Madonna Taught Rosie O’Donnell About FameOct 1, 20243614Rosie O'Donnell’s famous friends tell her she’s no good at being a celebrity. And if she’s honest, she’s never really felt like one. Despite her iconic roles and mass appeal, Rosie says she always identified more with the viewers at home rather than the stars she was interviewing on her long-running talk show. We got together in person to discuss all this, plus the devastating loss she suffered as
EXCLUSIVE PEEK: Reflections on Lisa Loeb and Kathleen HannaSep 28, 20241156You can get even more Fail Better with Lemonada Premium, where I share the extended thoughts I have after each interview. Here’s a free peek at what you could be getting: My conversation with Lisa Loeb, that came out earlier this week, really unlocked some things for me. Plus, it dovetailed well into some of the thoughts I was having after talking with another musician recently, Kathleen Hanna. Li
Why Lisa Loeb Struggles to Finish a SongSep 24, 20243411Lisa Loeb has the mind of a student — a straight-A, Grammy-winning student. As we talk, she moves between earnest curiosity and a dogged determination to succeed, and it’s clear to me that Lisa’s robust musical career (extending way beyond her hit song “Stay (I Missed You)”) has a lot to do with how hard she fought to open the doors that were closed on her. From less than ideal musical collaborati
Andy Cohen’s Concept of RealitySep 17, 20242985When a young Andy Cohen sat in front of his family’s TV watching hours and hours of soap operas, his mother grew increasingly concerned about his future: Was he destined to become an “airhead”? But Andy’s obsession with melodrama paid off. He’s defined modern television as executive producer of the Real Housewives reality show franchise, and he’s spent 15 years as the host of the boundary-pushing
Seth Meyers Loves When a Joke FailsSep 10, 20243259As a veteran late-night guest, I know a phony host when I see one — and Seth Meyers is as genuine as they come. He’s been a professional funny guy on TV for decades, first joining the cast of Saturday Night Live in 2001, then hosting his own late-night talk show since 2014. Over the years, he’s learned the hard way what works and what doesn’t, stumbling through creative missteps in front of millio