Reclaiming with Monica Lewinsky

This week on Reclaiming, we sit down with Jamie Kern Lima—entrepreneur, author, and trailblazing founder of IT Cosmetics, the billion-dollar beauty brand built on authenticity and inclusion. In this conversation, Jamie opens up about what she calls “doubting yourself out of your destiny,” and her “season of setbacks."She reflects on how persevering through countless “no’s” taught her the power of resilience, why creating products that reflected real women’s skin tones and needs was non-negotiable, and how listening to her gut—even when others didn’t believe—changed everything.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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 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.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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, 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!Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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, 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.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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, 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!)Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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 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. Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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’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. Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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 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.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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 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.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky now.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.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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 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.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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 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. Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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 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.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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 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.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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 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. Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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 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.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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 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.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky 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 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. Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky now.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.