Reclaiming with Monica Lewinsky

This week on Reclaiming, we’re playing one of our all time interviews with comedian, writer, and host John Oliver— a candid and thoughtful conversation about comedy, shame, and the power of laughter. John and Monica first connected in 2019 when she was interviewed for Last Week Tonight and she shares how that moment ultimately 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!)

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Emmy-winning creator and star of the TV series Crazy Ex-Girlfriend, Rachel Bloom joins Monica this week on Reclaiming for a revealing conversation about turning your personal trauma into creative expression. Rachel retraces her path from childhood OCD and early career love triangles, to creating Crazy Ex-Girlfriend—a show that brilliantly dismantled romantic-comedy tropes and reclaimed the "crazy" label with a raw, honest portrayal of mental illness. Expect a conversation brimming with intellectual curiosity, radical candor, and a masterclass in how to find the perfect punchline for your deepest pain...plus Rachel dishes on her latest role in The Devil Wears Prada 2.

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Actress, entrepreneur, and 90s icon Jennie Garth joins Monica this week on Reclaiming for a conversation about surviving global fame, reclaiming your purpose, and the profound power of choosing yourself. Jennie retraces her path from a quiet horse ranch in Illinois to the center of a cultural phenomenon as Kelly Taylor on Beverly Hills, 90210. She opens up about the personal cost of that fame—developing crippling anxiety and agoraphobia at the height of her success—and how she has since reclaimed the toxic “rivalry” narrative with and her 90210 female co-stars Jennie reveals how a single line from a 90210 script became the mantra for her second act, and how a pivot at 50 offered a different kind of healing than her acting career ever could. Expect a conversation brimming with surprising vulnerability, hard-won wisdom, and a roadmap for how to reclaim your own story, no matter how the world has tried to write it for you.
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Emmy-nominated writer, actor, and co-creator of the critically acclaimed series PEN15, Anna Konkle joins Monica this week on Reclaiming for a conversation celebrating how dark humor can get you through almost anything. Anna retraces her path from a chaotic childhood to co-creating PEN15—a show that lets everyone process the tragicomedy of adolescence. She opens up about a five-year estrangement from her father that ended abruptly when she became his sole caregiver in his final months, and about the ways she’s been able to recategorize her mom—from a source of eye-rolling to a source of admiration. Anna reveals why now was the time to explore grief and reconciliation in her debut memoir, The Sane One, and how the solitary act of writing offered a different kind of healing than collaborative television. Expect a conversation brimming with laughter, warmth and tragicomic story swapping between Monica and Anna.
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Renowned intuitive and bestselling author Laura Day joins Monica this week on Reclaiming for a pragmatic and enlightening conversation about turning trauma into a superpower and reclaiming intuition as a practical tool for living. Laura recounts the harrowing story of her traumatic childhood—caring for her younger siblings amidst profound neglect—and explains how the hyper-vigilance she developed to survive became the foundation for her intuitive gifts. She reveals the 16-year journey to writing her most definitive book, The Prism, and shares why her core philosophy is "proof over belief," a principle that earned her the title "The Psychic of Wall Street.” Listen for a masterclass in how to stop looking backward to heal, why the answers are rarely "inside you," and what it takes to reclaim your future by making one small, targeted change today.
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