Armchair Expert with Dax Shepard

Best of Monday 2025 (December 22, 2025)

Host: Dax Shepard
Co-host: Monica Padman

Episode Overview

This “Best of Monday 2025” episode is a highlight reel celebrating Top Moments from the Armchair Expert’s 2025 interviews. Dax Shepard and Monica Padman revisit and react to standout stories and intimate conversations with a diverse slate of guests, ranging from comedians and musicians to actors and writers. The episode centers on vulnerability, growth, the winding paths of creative careers, and the universal messiness of being human.

Key Discussion Points & Insights

1. Celebrity Encounters and Imposter Syndrome

With Nikki Glazer ([02:30]-[04:45])

• Nikki at the Grammys: Nikki shares how intimidating high-profile events can be, admitting to feeling small—despite her own nomination.
  • “I feel like I don’t belong there…even though I was nominated for a Grammy, but, like, I didn’t win. I was so mad.” ([02:32])
• Her boyfriend coaches her on the value of connecting with peers, but Nikki can’t bring herself to approach icons like Taylor Swift:
  • “I just don’t want her to make a less great song because she had to be like, ‘nice to meet you, oh,’ and like, hold me as I’m crying.” ([03:28])
• Monica echoes the post-awards "depression" of seeing through the Hollywood facade:
  • “No matter how big you get, you kind of worry about who’s in the room, who’s looking at you, where you’re seated. I kind of go through a depression afterwards.” ([04:24])
• Dax summarizes:
  • “It’s seeing the magic trick a bit. You realize, oh, there isn’t any pixie dust.” ([04:41])

2. Comedy, Consent & Roasts

With Dax & Monica ([06:16]-[10:02])

• Monica revisits writing a roast joke years before her show began and confronts feelings of hypocrisy and unintentional repetition in comedy.
• Dax reflects on his time on Punk’d, making jokes at celebrities’ expense to be “invited to the party,” and later bumping into hurt targets.
  • “For years, I’m bumping into Timberlake, and he hates my guts… Don’t you understand, buddy? I was, like, dead broke, and that was my only chance.” ([08:00])
• They discuss the consent implicit in celebrity roast culture.
  • Monica: “At Roast, I feel like everything’s on the table because they’ve signed up for it.” ([08:17])
  • Dax: “We should make a distinction...Tom Brady’s getting $25 million. He has consented.” ([08:28])
• Both admit to being sensitive, avoiding reading comments, and needing to protect their mental health:
  • Monica: “I’ve been sober from comments, which I think should be a thing.” ([10:22])

3. Trauma, Displacement & Family Survival

With Mo Amer ([11:01]-[16:28])

• Mo shares the shock of the 1990 Gulf War disrupting his childhood and family stability:
  • “It was the first time I knew that we were stateless...I didn’t know anything was wrong.” ([13:33])
• Harrowing stories of soldiers invading his home, threatening family, and his father being forced to aid the invading army.
  • “They got to our house at one o’clock in the morning...They were threatening my mom, my dad...they were going to throw a grenade in the bedroom.” ([14:00])

4. Near-Misses, Self-Sabotage, and Luck

With Brad Pitt ([18:02]-[23:23])

• Brad jokes about never having had a “gay experience” then reveals he left college just before fully graduating, drawn to L.A. by opportunity.
  • “I had one week left...but I just decided, done. I don’t want to do this.” ([18:45])
• The desperate, catch-22 of trying to get a SAG card, and embarrassing efforts to “get in”:
  • “You can’t get a job, you don’t have your SAG card, but you can’t get your SAG card unless you’ve had a job.” ([22:28])
  • On chaos: “Like a jackass...I go, ‘Would you like anything else?’ The first AD runs over: ‘You do that again, you’re out of here.’” ([23:15])

5. Addiction, Jail, and Unlikely Success

With Dominic Fike ([28:47]-[36:42])

• Dominic explains using drugs under house arrest, failing a test, and being jailed—then releasing a mixtape from jail that sparked a $4 million bidding war for his music.
  • “These dudes start flying from California to visit me in the jail. I’m at the phone like this with this dude that’s like, ‘Hey Dominic, you ready to be a millionaire?’... I’m homeless, doing this for a penny, under $4 million.” ([33:05])
• The juxtaposition of family crisis, producing art, and meteoric fortune is intense:
  • “My mom is in jail, my dad’s in jail...my sister’s up for adoption. So, you know, each lawyer for them is 200 grand. I’m like, this is my work that y’all are buying.” ([35:02])

6. Parental Loss, Depression, and Boundaries with Grief

With Dove Cameron ([37:03]-[46:21])

• Dove details efforts to reconnect with her suicidal, depressive father, and the painful confusion kids feel about parental withdrawal.
• “I thought he was mad at me...when you’re a kid, like, you blame yourself, of course.” ([39:01])
• Dax and Monica discuss the limits of storytelling around personal trauma, the need to keep parts private:
  • “Some stuff you can keep for yourself. Not because you’re hiding it out of shame, but just, it’s yours to keep and you should keep it.” ([44:26])
• A poignant moment around Dove’s tattoo:
  • Monica: “What is the tattoo, if you don’t mind sharing?”
  • Dove: “It says ‘we’ll be friends forever,’ which is just, like, the sweetest.” ([45:46])
  • Dax, emotionally: “If they had to tattoo that on them at some point, ‘cause something went sideways, you know, it’s just heartbreaking.” ([45:34])

7. Struggles in Hollywood: Persistence & the Long Road to Success

With Alexander Skarsgård ([53:05]-[59:15])

• Skarsgård’s “overnight” break didn’t lead to immediate success; after Zoolander, he spent years unable to find work.
  • “I went to Zoolander...and I booked that baby...[then] nothing happened for a long time.” ([53:05])
• Describes years of rejected auditions, financial stress, and the humbling experience of being an outsider in Hollywood.
  • “I was constantly worried that [my agency] would drop me because I wasn’t booking anything.” ([54:33])
• On the surreal transition to exclusivity and fame:
  • “I wanted that...and I have it, and I love that...but I can’t...walk up to a bouncer... If there’s a line, I can’t walk up and be like, ‘what’s up, let me in.’” ([58:06])

8. Motherhood, Regret, and Accepting "the Other Side"

With Jennifer Aniston ([59:25]-[64:26])

• Monica, vulnerable, opens up about her struggles with fertility and the peace (and complexity) in accepting a life without children:
  • Jennifer: “There’s a point where it’s like, it’s out of my control. There’s literally nothing I can do about it…But is there the moments of, ‘Hmm’? Of course. That’ll pass in three seconds.” ([61:07])
• They discuss the liberation on the other side of acceptance and fleeting feelings of “what could have been.”

9. Women’s Sexuality, Representation, & Late Bloomers

With Mindy Kaling ([74:28]-[82:00])

• Mindy on writing about ambitious, horny women—how her teen experience shaped her show’s sexual politics:
  • “My shows have a lot of horny women. My friend BJ Novak makes this joke: every trailer for any Mindy Kaling show has a hot man’s torso in slow motion.” ([74:39])
• Monica and Mindy share their late sexual debuts, combating stigma, and hoping to normalize varying trajectories for future generations.
  • “I now that I have three children, definitely want to destigmatize this.” (Mindy, [80:12])

10. Parental Death, Achievement, and the Roots of Motivation

With Adam Scott ([65:06]-[72:40])

• Adam processes grief through work, describing the loss of his mother as “part of the sky going away.”
  • “When she was gone...part of the reason I was doing this in the first place was for her to see it.” ([72:40])
• Dax and Monica reflect on the unique and deeply embedded role of mothers, and the thankless, unbreakable tether that shapes so much of our identities.

11. Self-Sabotage & Mystique of “Easy” Success

With Charlie Sheen ([82:00]-[88:21])

• Charlie tells an infamous story of nodding off during a movie shoot, trying to “wake up” by putting ice up his butt.
  • “I said, ‘I need a cup of ice...just the ice’...I stick an ice cube up my butt... and was suddenly wide awake...There’s footage of these takes in the movie, which is incredible.” ([83:57])
• Dax and Monica probe whether ease of success triggers self-sabotage in high performers, with Charlie’s life as a case study.

Notable Quotes & Memorable Moments

• On Self-Doubt at the Grammys
  • “I just wanted to have a reason to be there. So I was being very small.” – Nikki Glazer ([02:32])
• On Comedy, Hypocrisy, and Roast Culture
  • “Even when I get mad, everyone’s such a hypocrite.” – Monica Padman ([06:24])
  • “I’ve been on Conan making fun of the cast of The Expendables...maybe Sly was at home, bombed.” – Dax Shepard ([06:46])
• On the Loss of Magic in Hollywood
  • “It’s seeing the magic trick a bit. You realize, oh, there isn’t any pixie dust.” – Dax Shepard ([04:41])
• On Childhood Trauma and Loss
  • “It was the first time seeing your parents so worried.” – Mo Amer ([14:00])
• On Acceptance After Loss
  • “There’s a point where it’s like, it’s out of my control. There’s literally nothing I can do about it.” – Jennifer Aniston ([61:07])
• On Cherishing Boundaries with Painful Stories
  • “Some stuff you can keep for yourself. Not because you’re hiding it out of shame, but just, it’s yours to keep and you should keep it for yourself.” – Dax Shepard ([44:26]).
• On Achievement and Parental Approval
  • “When she was gone...part of the reason I was doing this in the first place was for her to see it.” – Adam Scott ([72:40])

Important Timestamps

• [02:30-04:45] Nikki Glazer on award show imposter syndrome & the post-celebration letdown.
• [06:16-10:22] Dax & Monica on the ethics of roasting, consent, and emotional aftermath.
• [11:01-16:28] Mo Amer’s firsthand account of the Gulf War’s impact on his family.
• [18:02-23:23] Brad Pitt’s meandering path to Hollywood, self-sabotage, and getting started.
• [28:47-36:42] Dominic Fike: jail, trauma, and signing a $4M record deal.
• [37:03-46:27] Dove Cameron on her father’s depression, loss, and memory tattoos.
• [53:05-59:15] Alexander Skarsgård on years of rejection and the surreal nature of fame.
• [59:25-64:26] Jennifer Aniston and Monica discuss fertility, regret, and finding peace.
• [74:28-82:00] Mindy Kaling and Monica dig into representation, late bloomers, and dating taboos.
• [65:06-72:40] Adam Scott: grief and how mother’s approval motivates achievement.
• [82:00-88:21] Charlie Sheen: self-destruction, strangeness, and waking up on set.

Tone & Atmosphere

• Warm, self-deprecating, and candid: Both hosts and guests toggle between hilarious, deeply personal, and sometimes dark recollections—but always with an undercurrent of empathy, humor, and resilience.
• Emphasis on vulnerability: Almost every story returns to the theme that the “messiness" of being human—whether in failure, coping, or eccentricity—is not just forgivable, but beautiful.
• Safe space for confession: The show’s strength lies in its guests’ willingness to admit to imperfection, regret, shame, and the desire for connection.

Summary

"Best of Monday 2025” aggregates a year’s worth of human truths: creative anxiety and imposter syndrome at celebrity events, the blurred ethics of comedy, the enduring aftershocks of family trauma, the impossibility of “having it all,” and the long tail of hope and heartbreak. Dax’s anthropology background and Monica’s mix of sharpness and vulnerability create a podcast that isn’t just a celebrity highlight reel—it’s a warm, chaotic, honest survey of why no one feels fully at home in their own story, and why that might be a universal relief.

Listeners are left with a patchwork of wisdom: Hold boundaries around private pain, laugh at your own contradictions, connect when you can, and forgive the mess.