Monica Shares Her Unforgettable Moments of the ‘Reclaiming’ Podcast

All year long, people have asked Monica the same question: Who’s been your favorite interview? And all year long, the truth has been the same — there was something unforgettable in every single conversation. So for this special compilation, we’ve pulled together some of the most powerful, lingering moments of 2025 into one episode.

From Miley Cyrus talking about shame, sexuality, and the collateral damage of fame, to Alan Cumming confronting his abuser, to Chelsea Handler cracking open decades of armor over a single orange, these are the stories that stayed with us. Jurnee Smollett and Gabrielle Union explore blood memory and ancestry; Mark Duplass names “the woog” that lives between anxiety and depression; Sarah Paulson and Allison Janney reflect on childhood survival strategies and the characters that shaped them. Tarana Burke reframes grace, John Oliver and Margaret Cho show how gallows humor can literally save us, Molly Ringwald and Adam Scott unpack the long tail of fame, Olivia Munn reclaims her mastectomy scars, Beanie Feldstein talks about grief and language, Jon Chu and Tony Hawk share the hustles and crash landings behind their legends, and Elise Loehnen and Courtney Smith dig into the high cost of reputational harm — especially for women.

And because Reclaiming is never just one thing, we even tucked some of the year’s funniest, most unhinged moments at the end — from sex vocabulary lessons to Broadway “up the butt” lore to John Oliver’s favorite four-letter word. It’s a season of memorable moments, in one episode: raw, reflective, heartbreaking, and laugh-out-loud ridiculous in all the best ways.

00:00 Introduction and Episode Overview
00:26 Miley Cyrus: Personal Struggles and Public Perception
03:18 Confronting Family and Personal Demons
08:11 Exploring Transgenerational Trauma and Epigenetics
13:55 Gabrielle Union's Journey to 50
24:51 Childhood Trauma and Coping Mechanisms
35:14 Exploring the Concept of Grace
36:29 Interview with the Dalai Lama
41:04 Dark Humor and Personal Struggles
43:00 Reflecting on Iconic Film Roles
47:34 Therapy and Personal Growth
49:43 Breast Cancer Awareness and Empowerment
53:44 Experience Camps and Grief Support
01:01:23 Navigating Fame and Relationships
01:05:49 Reputation and Cultural Commentary
01:08:47 Humorous Anecdotes and Final Thoughts

Watch more episodes of Reclaiming:    • Reclaiming with Monica Lewinsky  

Follow Reclaiming with Monica Lewinsky on social:
  / reclaimingwithmonica  
  / reclaimingwithmonica  

Connect with Monica:
  / monica_lewinsky  
https://x.com/monicalewinsky
  / monicalewinsky  

Connect with Wondery:
Connect with Wondery
  / wonderymedia  
  / wonderymedia  
  / wonderymedia  
https://x.com/wonderymedia

About the show:
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. Listen to Reclaiming with Monica Lewinsky premieres early and ad-free at https://wondery.com/shows/reclaiming-....

#monicalewinsky #podcast

Monica Shares Her Unforgettable Moments of the ‘Reclaiming’ Podcast
   • Monica Shares Her Unforgettable Moments of...