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.
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Cindy Crawford
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.
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Andrew Rannells
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.
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KESHA
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.
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Savannah Guthrie
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.
If you’re interested in unexpected conversations that go uncharted places, are remotely self-aware and like to laugh, then please join me as I continue to find my public voice on Reclaiming with Monica Lewinsky. (That’s me.) I will have honest, wide-ranging interviews with all kinds of people – recognizable names, regular folks, experts and friends – about what it means to reclaim what’s been lost or taken in the broadest sense. Every week, I’ll draw from my own unique experiences (like say, surviving a global scandal at 24 years old), and delve into the personal and often messy ways people find their way back to themselves. And because I love a good tangent, we’ll probably also touch on other stuff, too.Follow Reclaiming on the Wondery App or wherever you get your podcasts. Watch new episodes on YouTube, or listen to Reclaiming early and ad-free by joining Wondery+ in the Wondery App, Apple Podcasts, or Spotify.
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