Reclaiming with Monica Lewinsky

This week on Reclaiming, we sit down with Mark Duplass—actor, filmmaker, writer, and creative force whose career has stretched across indie film, television, and music. In this conversation, Mark opens up about his personal journey with anxiety and depression, and how he works to keep what he calls “the woog” at bay. He reflects on the tools that help him navigate those darker stretches, the importance of naming what scares us, and how leaning into vulnerability can become its own form of resilience.He also shares his evolving perspective on creativity, fatherhood, and partnership, and why showing up authentically online—even in the messiness—can foster a kind of intimacy that transcends likes and algorithms.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, Monica is joined by Liz Gilbert, bestselling author of Eat, Pray, Love and City of Girls, for a deeply personal conversation about solitude, self-compassion, and the courage to live outside expectation. Liz opens up about the liberation she’s found in celibacy, the radical practice of befriending herself, and the cost of female over giving. She and Monica talk about loneliness, freedom, recovery, and what it means to say: this isn’t working for me. It’s a candid and soulful episode about grief, transformation, and the power of reclaiming your own life. And make sure to check out her new book "All the Way to the River" out now!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sit down with Julia Fox—actress, artist, author, and unabashed cultural provocateur who has turned fearlessness into a full-blown art form. In this conversation, Julia opens up about the importance of having a positive male role model for her son, the determination not to let the demons of her past overshadow the blessings of her future, and how she manifested—yes—a sugar daddy. She reflects on her meteoric rise from the New York art scene and doing sex work to breaking into Hollywood, her sometimes rocky relationship with her parents, her perspective on being a muse, and the politics of beauty.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, Monica is joined by Pulitzer Prize winning journalist Ronan Farrow for a conversation that’s as vulnerable as it is incisive. From growing up under relentless scrutiny to reporting on some of the most powerful men in the world, Ronan opens up about the emotional toll of telling the truth and the unexpected ways trauma can shape ambition. They talk, disinformation, misplaced reality, and the quiet bravery of choosing compassion in a world that rewards cruelty. It’s a revealing and unexpectedly tender episode with one of journalism’s most fearless voices. Plus, Monica talks about the time she got catfished by a fake Greta Thunberg.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, Monica is joined by Amanda Knox—advocate, writer, and executive producer of the new Hulu series The Twisted Tale of Amanda Knox—for an unflinching and deeply personal conversation about identity, injustice, and the long tail of trauma. From being wrongly imprisoned for her roommate’s murder at 20 years old to reclaiming authorship over her own story, Amanda reflects on the cost of being turned into a symbol—and the strength it takes to become a person again. They talk about shame, survival, and what it means to be thrust onto a global stage as a young woman in the public eye. It’s a candid and emotionally layered episode about truth, bias, and the power of finally being heard.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sit down with comedian, writer, and host John Oliver for a candid and thoughtful conversation about comedy, shame, and the power of laughter. John reflects on his interview with Monica in 2019 for Last Week Tonight and how that moment became part of her reclaiming journey. They explore the ethical tightrope of making jokes in a world full of gray areas and how humor can be both a coping tool and a way to call power to account. John shares what really surprised him about interviewing the Dalai Lama and the unexpected way His Holiness threw him off balance. With wit and depth, he and Monica dig into the weight of public shame, the risk of accountability, and why, for John, getting into trouble might just be the point. (And they use the C Word quite a bit!)See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we talked to, beauty mogul, author, advocate, and all-around force, Victoria Jackson,. She built a multi-million-dollar makeup empire out of her garage, TRADEMARKED the no makeup - makeup look, and later helped bring three life-saving drugs to market after her daughter was diagnosed with a rare disease. We talked about reclaiming self-worth, purpose, and joy, and what it means to keep reinventing yourself at every stage of life. OH, AND DID YOU KNOW ONE OF HER MAKE-UP INFOMERCIALS WAS PLAYED AT THE VATICAN. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we’re joined by the hilarious Sarah Silverman, whose career has been built on saying the unsayable—and making us laugh through the discomfort. In this intimate conversation, Sarah opens up about the quiet heartbreak of losing both her parents, the shame and humor of wetting the bed well into her teens, and the evolving landscape of comedy in a culture that’s constantly redefining its boundaries. With her signature blend of sharp intellect and raw honesty, she explores how pain shapes perspective and why vulnerability might just be the truest form of rebellion. It’s a candid, surprising, and deeply human episode with one of comedy’s most enduring provocateurs. And as a bonus, Monica makes another WAP-like discovery. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sit down with supermodel, entrepreneur, and icon Cindy Crawford for a candid and vulnerable conversation about grief, perception, and personal agency. Cindy opens up about the childhood loss of her younger brother and how that early heartbreak shaped her perspective on life, family, and resilience. She reflects on the challenges of being underestimated because of her beauty, and how she’s spent decades building a career for herself that extends beyond modeling. We hear the story behind how Cindy and her supermodel counterparts—Naomi, Linda and Christy— worked to own their narrative of 90's stardom and how the modeling industry has changed for this generation. With grace and clarity, Cindy shares how she’s stayed grounded and grateful through it all.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sit down with actor and author Andrew Rannells for a candid, funny, and deeply reflective conversation about identity, family, and the roles—onstage and off—that have shaped his life. Andrew opens up about growing up gay and Catholic in Omaha, Nebraska, and how those early years informed both his sense of humor and his search for belonging. He shares what it was like to skyrocket to fame with his Tony-nominated performance in The Book of Mormon, and later, to challenge audiences (and himself) as Elijah on HBO’s Girls. But some of his most meaningful roles have been far from the spotlight—like learning how to be a stepparent and navigating adulthood on his own terms.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this deeply soulful and wide-ranging conversation, Monica sits down with singer, songwriter, and now record label founder Kesha to talk about healing, spirituality, and the long road to joy. Kesha opens up about her fight for autonomy, the emotional toll of public scrutiny, and how her spiritual journey and her work with Rick Rubin helped her reconnect with herself. From crystals and plant medicine to reclaiming her voice in every sense, this episode is a celebration of vulnerability, truth, and radical self-love. She also shares why she made the decision to change the opening lyric in her hit song ""TikTok"" as an act of solidarity and advocacy. Plus, Kesha talks about the inspiration behind her new single Joy Ride and what the “Tits Out Tour” really means.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sit down with journalist, attorney, and Today Show anchor Savannah Guthrie for a candid and heartfelt conversation about ambition, loss, faith and trusting the unexpected. Savannah reflects on her early days as a young intern in Washington, D.C., when dreams of law and journalism collided, and the serendipitous turns that shaped her path forward. She opens up about the profound grief of losing her father at sixteen—and how that loss carved out a sense of resilience and clarity that still guides her today. We explore the power of intuition, the courage it takes to say yes to uncertain opportunities, and the grace found in honoring both ambition and surrender.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sit down with actor, writer, and musician Josh Radnor for a soulful, searching conversation about identity, creativity, and the lessons that come from letting go. Josh reflects on the surreal weight of becoming a household name through How I Met Your Mother—and the years it took to untangle his sense of self from the character of Ted Mosby. He opens up about his deepening relationship with music, the healing path of spiritual exploration—including transformative experiences with ayahuasca—and how those journeys helped him reconnect with purpose beyond fame. We also unpack the value of failure, the discomfort of being misunderstood, and why Josh believes that confronting our self-consciousness, rather than avoiding it, can be one of the most powerful catalysts for personal growth. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sit down with the iconic Brooke Shields—actress, model, author, and lifelong performer whose career has spanned decades and defied expectations. In this conversation, Brooke opens up about aging in the public eye and the freedom she’s found in embracing it on her own terms. She reflects on the joy and vulnerability of live performance, her deep love of comedy, and why making people laugh has become one of the great pleasures of her life. We also explore her unexpected passion for science, as Brooke shares candid thoughts on Darwin, natural selection, and how survival of the fittest plays out not just in nature—but in Hollywood.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sit down with Miley Cyrus, a global icon, shape-shifting performer, and fearlessly candid storyteller. Miley opens up about her earliest days in the spotlight, the complicated legacy of Hannah Montana, and the personal cost of growing up famous. She shares why her latest music feels like medicine, how she’s learned to set boundaries with the public, and the lessons she’s still unlearning about shame, identity, and self-worth. With humor, honesty, and striking insight, Miley opens up about family estrangement and reconciliation, the armor of persona, and why she’s finally starting to feel free in her own skin.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we are joined by actor and activist Sophia Bush. Sophia discusses the journey of learning to trust her instincts after experiencing workplace trauma, navigating public scrutiny during personal transitions, and discovering the power of righteous anger. Sophia shares profound insights about the "character" we become in others' eyes versus our authentic selves, and how somatic practices have helped her reconnect with her body after years of disconnection. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sat down with bestselling author and activist Glennon Doyle to discuss self-trust, authenticity, and personal transformation. Glennon opens up about her ongoing journey with eating disorders, recovery, and her relationship with being in the public eye. Plus we explore the power of somatic therapy, listening to one's body, and setting boundaries - even when it's uncomfortable.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sit down with beloved author and truth-teller Anne Lamott, whose words have offered solace and light to generations of seekers. In this heartfelt conversation, Anne dives into the transformative power of grace, the messy art of forgiveness, and the lifelong unraveling of perfectionism and codependency. With her unique mix of wit and vulnerability, she shares stories of stumbling and surrender, reminding us that healing often begins when we stop trying to fix everything. Through laughter, insight, and deep compassion, Anne invites us to embrace the imperfect, the tender, and the beautifully human. Don’t miss this soulful and deeply nourishing episode with a writer who helps us find depth in the daily grind.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we talk with visionary Andrew Yang, the entrepreneur, former presidential candidate, and champion for a new kind of democracy. In this enlightening conversation, Andrew shares his bold ideas for transforming the American political landscape, including the case for term limits, the need for more than just two political parties, and his passionate advocacy for Universal Basic Income. He reflects on his journey from outsider to political reformist, the challenges of pushing for systemic change, and why the future of democracy depends on new solutions. We also explore how he’s working to inspire a new generation of leaders who are ready to rebuild the foundations of governance. He’s also funny. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sit down with the unflinching and fiercely funny Tig Notaro, a comedian whose honesty and humor have redefined the boundaries of stand-up. In this raw and revelatory conversation, Tig opens up about the life-threatening battle with C. diff that left her physically depleted, and the surreal moment that followed just months after —when she stepped on stage just days after being diagnosed with cancer to deliver what would become one of the most iconic comedy sets of our time. She also speaks candidly about the devastating loss of her mother, who passed away while Tig was still in the hospital herself, and how that grief compounded an already unimaginable chapter of her life.With her signature deadpan delivery, Tig reflects on how facing mortality reshaped her approach to comedy, creativity, and connection. She shares her thoughts on emotional growth, vulnerability, and what it means to truly reclaim your life in the aftermath of trauma.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we are joined by the youngest person to ever top the billboard 100, artist JoJo Levesque, who takes us behind the curtain of her remarkable 20-year career in music. In this raw and revealing conversation, she opens up about her complex path to self-discovery, her fight to reclaim her artistic freedom after a devastating label dispute that kept her music hostage, and the personal battles that shaped her into the powerhouse vocalist we know today. From teenage superstar to industry warrior, JoJo shares untold stories of resilience, music industry manipulation, and the emotional toll of growing up in the spotlight.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sit down with the pioneering Margaret Cho, the legendary comedian, actress, and activist who has spent decades breaking barriers and challenging norms. In this candid conversation, Margaret reflects on her journey to becoming an icon for both the Asian and LGBTQ+ communities, the responsibility that comes with visibility, and the power of comedy as a tool for change. She opens up about her lifelong struggles with body image, the evolving conversation around self-acceptance, and how she continues to navigate an industry that hasn’t always embraced diversity. We also dive into her latest special, Psy-Cho, where she fearlessly takes on politics, identity, and the absurdities of modern life with her signature sharp wit. With humor, honesty, and an unshakable sense of self, Margaret reminds us that true freedom comes from owning our stories—flaws, fears, and all.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sat down with comedy powerhouse Chelsea Handler for a conversation that peels back the layers of her signature confidence and wit - and oh did we laugh! Chelsea opens up about the profound loss of her brother and how his death shaped the trajectory of her life. She candidly discusses her late-in-life embrace of therapy, offering her thoughts into why it's never too late for self-discovery. We also explore societal expectations around motherhood and how Chelsea has cultivated meaningful relationships with children in her life while remaining true to her decision not to have children of her own.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week, Monica sits down with skateboarding pioneer Tony Hawk. Tony reflects on the physical toll of his most severe injuries and revisits what it felt like during the historic moment when he landed the 900 at the '99 X Games. Then, Tony opens up about his newest role as grandfather, and shares his unique connection with the late Kurt Cobain, and why he's still actively skating and dropping in at local skateparks.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we chat with the brilliant Beanie Feldstein, the actor who brought a pivotal chapter of Monica's life to the screen. Beanie opens up about the challenges of portraying a real person, the emotional depth of stepping into someone else’s story, and the power of storytelling to shift narratives. Beyond the screen, she shares how personal loss shaped her, from navigating her own grief after the death of her brother, to becoming a counselor at Experience Camps, where she helps grieving children find healing. She also reflects on the joy of her wedding day -- the magical venue, a prophetic dream, and matching Gucci. With warmth and humor, Beanie speaks about love, loss, and family. Don’t miss this heartfelt and deeply personal conversation.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we are joined by visionary Director Jon M. Chu. Jon reflects on his extraordinary career path, delving into how themes of identity and representation have become cornerstones of his cinematic storytelling. We explore the creative processes behind the scenes of Wicked and Crazy Rich Asians, uncovering how these films evolved into the beloved classics we know today. Plus, Jon offers a glimpse into his highly anticipated Britney Spears biopic. Tune in for an enlightening and captivating discussion with one of Hollywood's most influential filmmakers.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sit down with trailblazer Tarana Burke, the activist and leader whose powerful voice helped to spark a global movement. In this candid conversation, Tarana opens up about the origins of Me Too, revealing the deeply personal experiences that fueled her lifelong fight for justice. She sheds light on the complexities of power dynamics, the resilience of those who have felt unheard, and the ongoing work of creating safer spaces for all. With wisdom, warmth, and unshakable determination, Tarana reflects on the victories, the challenges, and the path forward in a world still reckoning with long-overdue change. Don’t miss this inspiring and thought-provoking episode with the woman who turned a phrase into a revolution.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we sit down with the incomparable Molly Ringwald, the actress who defined a generation and shaped '80s pop culture forever. In this intimate conversation, Molly pulls back the curtain on her meteoric rise to fame, sharing candid revelations about navigating Hollywood as a teenage icon. She offers a fascinating glimpse into her creative partnership with legendary director John Hughes, and reveals the untold story of how her own headshot unexpectedly inspired the classic ""Pretty in Pink."" Plus, Molly reflects on her years in Paris, where she rediscovered herself away from the American spotlight. Don't miss this nostalgic yet deeply personal episode with the original teen queen who continues to captivate audiences decades later.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Reclaiming, we welcome renowned tech journalist and industry expert Kara Swisher. Kara offers a thoughtful prediction on the political landscape under Trump and Musk. She drops a provocative take on AI's gender problem and why she believes men are at the heart of it and she even shares her personal reflections on pregnancy. Don't miss this no-holds-barred conversation with one of Silicon Valley's most influential voices.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this deeply personal episode, Monica chats with actor and Traitors presenter Alan Cumming, who shares his story of surviving an abusive childhood with a father obsessed with his hair and the lasting impact it left on him. He reflects on the power of speaking openly about his trauma, how sharing his story has helped him heal, and why he still struggles with the fear of becoming a father himself. It’s an honest and raw conversation about breaking cycles, confronting the past, and learning to move forward.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode, Monica sits down with actress, women’s health advocate, and breast cancer survivor, Olivia Munn for a candid conversation about resilience, self-discovery, and healing. Olivia reflects on her childhood experiences with bullying and how her stubbornness helped shape her fierce, determined spirit as an adult. She also discusses the lessons she’s learned in the industry, the mindful practices that keep her grounded, and her journey through a breast cancer diagnosis—including the challenges of a mastectomy and her bold decision to reveal her scars in her iconic Skims campaign. With an honest, down-to-earth conversation, this episode offers real talk on resilience, growth, and learning to live in the now.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In the powerful premiere of Reclaiming with Monica Lewinsky, Monica reflects on how she found the strength to take back her story after the scandal that turned her life upside down. With raw honesty, she opens up about the years of public shame, personal struggle, and the turning point that led her to reclaim her voice. This episode offers an intimate look at Monica’s journey from survivor to activist—and the strength it took to become the woman she is today. Interviewed by Elna Baker.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Listen to Reclaiming with Monica Lewinsky wherever you get your podcasts on February 18. You can listen ad-free on Wondery+. Join Wondery+ in the Wondery app or on Apple Podcasts.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.