Reclaiming with Monica Lewinsky: Memorable Moments of 2025

Podcast Host: Monica Lewinsky (for Wondery)
Episode Date: January 20, 2026
Episode Overview:
This special compilation episode brings together standout moments from the past year of “Reclaiming,” where Monica Lewinsky explores how individuals reclaim what’s been lost or taken. Featuring deeply personal, vulnerable, and often humorous conversations, guests range from celebrities and experts to activists and friends. The episode showcases raw honesty, the impact of fame and trauma, the lifeline of humor, generational healing, and moments of pure laughter, giving a true reflection of the podcast’s mission: finding your way back to yourself.

Key Segments & Discussion Highlights

1. Miley Cyrus: Fame, Shame, and Family (00:06–05:48)

• Miley relates her 2013 “fall from grace” to Monica’s own public scandal.
• Discusses the strain of public scrutiny on relationships: “If I kept dressing or acting a certain way, my relationships fell apart… No one wanted to date me because they didn’t want to be with a woman [whose] sexual expression part was not for them.” (00:45)
• She opens up about familial embarrassment and guilt, feeling “mortified” at family holidays and the impact on her siblings.
• Monica and Miley bond over shared experiences of public shame and ongoing guilt:

  “I still feel guilt. I still sometimes carry guilt around about that.” – Monica (04:23)

• Miley describes the relief she found through EMDR therapy, “It deleted the guilt and shame folder.” (05:10)

2. Alan Cumming: Confronting the Past (05:49–10:09)

• Alan details confronting his abusive father with his brother after years apart.
• Describes the tension and fear: “I thought my dad was going to hit me at one point… he had a stick and these boots making a crunchy noise.” (07:10)
• Explains his attempt to understand the lineage of abuse and the futility of seeking logic from those unwilling to face their actions:

  “You’re never going to get sense. You’re never going to get logic from someone who is mentally ill.” (08:40)

• Ultimately, he found it empowering to “give it back” to his father rather than carrying shame and protecting the abuser.

3. Chelsea Handler: Therapy, Oranges, and Breaking Open (10:10–13:30)

• Shares a breakthrough in therapy when her therapist handed her an orange, triggering deep emotion tied to childhood memories:

  “All of it… because he had done something so nice. An orange to me is like, the best memory I have of my childhood. I love oranges…and as I was peeling it…I was like, oh God, here I go…” (11:20)

• Discusses the importance of vulnerability, particularly in parenting:

  “If someone can break down, then you have access to try to heal them.” (13:05)

4. Jurnee Smollett: Blood Memory & Generational Trauma (13:31–19:40)

• Explores transgenerational (epigenetic) trauma and her multicultural heritage (“raised by a Black woman and my dad, Ashkenazi Jewish”) and its influence on her acting.
• Recounts filming “Underground” shortly after her father’s death, channeling ancestral pain in a whipping scene:

  “I felt completely taken over by spirit...That blood memory...does reverberate in moments that are important.” (18:45)

5. Gabrielle Union: Ancestral Connection and Rebirth (19:41–27:18)

• Describes her 50th birthday trip through Africa to reclaim herself and her family roots.
• Powerful scene at Elmina Castle and the River of No Return in Ghana—her mother’s collapse and hearing ancestors’ voices:

  “If you’re quiet enough, you can hear our ancestors speaking to us…when you listen…the ancestors show up.” (23:40)

• Discussion of shared transgenerational trauma with Monica, touching on Jewish and Black histories.

6. Mark Duplass: The ‘Woog’ and Family Language (27:19–32:35)

• Mark creates family terms like “the woog” to describe his own mix of depression and anxiety.
• Talks about somatic work during the pandemic, noticing disconnection from his body as a source of distress.
• Shares playful family anecdotes about inventing words and the relief play can bring.

7. Sarah Paulson: Shape-Shifting, Survival, and Forgiveness (32:36–37:22)

• Describes her adaptability as a survival mechanism from being left alone as a child.
• Uses magical thinking and shape-shifting to create security:

  “A way in which I survived the terror I felt…was to be whatever anybody needed me to be.” (33:45)

• Reflects on generational differences regarding emotional language and on forgiving her young, striving mother.

8. Allison Janney: Embodying CJ on “The West Wing” (37:23–40:12)

• Allison confesses she never watched “The West Wing” while it aired, feeling traumatized by her own associations post-1998.
• Sees CJ Craig as part her (“humor and femininity”), part Aaron Sorkin (“smarts”).
• Reflections on growing up in a family that avoided discussing politics.

9. Tarana Burke: “Cover Sins,” Mercy, and Grace (40:13–45:04)

• Tarana explains “cover sins”—invented transgressions she confessed as a child to protect her real trauma:

  “They were just cover sins for my actual sin, which was really, really, really, really bad.” (41:15)

• Explores the complexities of mercy and grace, arguing,

  “The people who are asked to give grace the most, usually the people who need it more.” (43:25)

• Ties the concept of grace to movements for liberation and social justice.

10. John Oliver: Humor with the Dalai Lama (45:05–49:55)

• Relates his apprehension about joking with the Dalai Lama:

  “[He] likes making people laugh…But as I was watching [people saying] ‘please don’t die,’ I realized the pressure he’s under.” (46:00)

• Only when Oliver got the Dalai Lama to laugh did the interview work:

  “The only way that conversation made any sense was when we were joking—and joking about hard things.” (48:40)

• The importance of “gallows humor” to break down status and connect as humans.

11. Margaret Cho: Surviving through Dark Humor (49:56–52:30)

• Margaret tells of a failed suicide attempt with characteristic dark comedy:

  “I hung myself from my shower curtain rod, but the rod started bending…I’m too fat to kill myself. So I got down and said, ‘I’ll try again when I reach my goal weight.’” (50:00)

• Discusses how humor at rock bottom is a sign of survival and healing:

  “Laughing is life affirming in a very, very granular, basic way.” (51:25)

12. Molly Ringwald: Being a Teenage Muse (52:31–56:23)

• Shares stories from her teens, how dancing with her gay best friend inspired John Hughes’ film “Pretty in Pink.”
• Reflects on being a muse at a young age, then coming to terms with the complexity (or potential weirdness) as an adult.

13. Adam Scott: Therapy, Career Anxiety, and Self-Doubt (56:24–59:09)

• Monica asks if therapists ever ask about show secrets; Adam admits he’s not in therapy but jokes about the value of a therapist as a confidant.
• Shares persistent insecurity in his career, even after success:

  “Whatever the feeling was when you started out, you’re sort of always there a bit…I think if I worry if I exhaled, then it would all come crashing down.” (58:20)

14. Olivia Munn: Scars and Self-Love after Cancer (59:10–1:02:56)

• Munn discusses baring her mastectomy scars in a Skims ad:

  “I was tired of being insecure about them…This is going to be proof of how hard I fought.” (1:00:33)

• Describes the impact on others, including a stranger’s mother, and her new resolve:

  “If I have the strength to [let go of emotional baggage], because it is strength to let go…then I’ll do it.” (1:02:31)

15. Beanie Feldstein: Grief, Camp, and Clear Language (1:02:57–1:08:25)

• Shares her family’s values of work ethic and generosity, and how grief after her brother’s death led her to volunteer at Experience Camps for bereaved children.
• Describes the healing power of community and direct language about loss:

  “Kids don’t understand euphemism…when you say ‘crossed over’…that doesn’t mean anything. They need to hear ‘died’ or ‘death’…it helps it sink in.” (1:06:15)

16. Jon M. Chu: Sneaking into the Oscars (1:08:26–1:11:00)

• The director recounts making a fake badge to sneak into the 2000 Oscars, getting caught, reprinting the badge, eventually getting backstage and even to the Governor’s Ball.
• On finally getting to attend the Oscars legally:

  “To be there now, legally…having a seat there is pretty amazing.” (1:10:47)

17. Tony Hawk: The Dual Edges of Fame (1:11:01–1:16:34)

• Hawk describes both the excitement and the relational toll of fame during and after his skateboarding peak.
• Explains how chasing fame distorted his ability to connect with loved ones:

  "I just knew I had to do something about...I was just ruining relationships left and right and, you know, wasn't connecting with my kids on a level that I felt I should have been." (1:15:00)

• Credits therapy and his wife’s support for helping him refocus on what truly matters.

18. Elise Loonan & Courtney Smith: The Dangers of Reputational Harm (1:16:35–1:21:12)

• Elise’s resonant quote:

  “All you have to say is that a woman is bad… and she’s done… Our culture is a graveyard of women’s reputations, and we are our own gravediggers.” (1:16:35)

• Discussion of the archetypal lesson of Monica’s story and the shared experience of “cancel culture.”
• Monica reflects on personal responsibility and culture’s double standards.

19. Lighthearted Outtakes: Sex, Slang & Laughter (1:21:13–End)

• Miley Cyrus, Sarah Silverman, Andrew Rannells, and John Oliver share memorable, hilarious moments:
  • Monica learns what “WAP” stands for (“wet ass pussy”) and about “the Stranger” (non-dominant hand handjob).
  • Sarah Silverman, Monica, and guests riff on family-friendly cursing, the “C word,” and inadvertently teaching their kids dirty words.

Notable Quotes

• Miley Cyrus: “I lost everything during that time in my personal life because of the choices I was making professionally.” (00:41)
• Alan Cumming: “We’re giving it back to you. I don’t want to carry this anymore.” (09:15)
• Chelsea Handler: “We can’t fix you until you break down. You know what I mean?” (12:40)
• Gabrielle Union: “If you’re quiet enough, you can hear our ancestors speaking to us…when you listen…the ancestors show up.” (23:43)
• Margaret Cho: “Laughing is an unexpected breath…laughing is life affirming in a very, very granular, basic way.” (51:19)
• Elise Loonan: "Our culture is a graveyard of women’s reputations, and we are our own gravediggers." (1:16:42)
• Beanie Feldstein: "The way that we are able to exist in joy and grief at the same time is something that I wish all of our society could feel..." (1:05:09)

Tone & Style

The episode balances depth with humor, self-reflection with storytelling, often using self-deprecation and candid conversational language. Monica’s openhearted, empathetic interviewing style invites guests to share both their wounds and their laughs, demonstrating the many ways one can “reclaim” themselves.

Recommended Listening Order

Listeners who want to focus on themes might seek out:

• Healing and Trauma: Miley Cyrus, Alan Cumming, Jurnee Smollett, Tarana Burke, Gabrielle Union, Tony Hawk
• Humor and Survival: Chelsea Handler, Margaret Cho, John Oliver, Mark Duplass, Monica’s comedic outtakes
• Legacy and Social Narrative: Elise Loonan, Courtney Smith, Molly Ringwald, Beanie Feldstein

For More

Reclaiming with Monica Lewinsky is available on Wondery and all major platforms.