You Made It Weird with Pete Holmes

Guest: Natasha Leggero (Returns)
Release Date: September 4, 2024
Main Theme: Comedian Natasha Leggero joins Pete Holmes to candidly discuss parenting, the anxieties around raising kids in a strange world, the internet’s impact, her new book "The World Deserves My Children," and the unique joys and burdens of being a modern woman, with signature sharp humor throughout.

Episode Overview

This episode features comedian Natasha Leggero returning to the podcast to discuss the realities and weirdnesses of parenting, the cultural moment we're living in, and her new book. Pete and Natasha bounce between hilarious social commentary and deeper reflections on technology, vices, generational anxieties, and maintaining a creative (and real) life amid it all. The conversation is intimate, honest, and consistently funny — with detours into pop culture, parenting fails, and being women (and men) of a certain age.

Key Discussion Points & Insights

1. Comedy, Friendship, and Creative Origins

[02:24 – 03:10]

• Natasha and Pete reminisce about feeling like they "started comedy together" and working in writers’ rooms; Moshe Kasher (Natasha’s husband) is referenced as part of their comedy “class.”
  • Natasha: “I feel like everyone in our class kind of started around 2000…”
• Mutual appreciation surfaces early — Pete won’t stop complimenting Natasha, jokingly overdoing it.
• Natasha’s new book, The World Deserves My Children, is introduced.

2. The Book, Parenting, and Modern Family Life

[03:26 – 05:29]

• The cover shoot for Natasha’s book, involved her real kitchen and daughter—a reflection of the pandemic era.
• Natasha discusses dedicating her book to her daughter, illustrating the existential conversations modern parents have with kids about legacy, choice, and even the place of technology in their lives:
  • Natasha: “My phone will be my child.”
    [05:40]

3. Technology Burnout, Social Media Satire & Parenting

[06:03 – 13:04]

• Both comedians joke about being out of touch with "the hawk tooie girl" and other trending memes, expressing alienation from viral culture.
  • Pete: “If you’re watching good television, good film, reading good books, talking to good people, looking at real shit, and someone shows you the hawk tooie girl, I’m fucking proud that I’m like, this is zero.”
    [07:11]
• Both use assistants for social media and confess to discomfort with having an online presence.
• Natasha: “My mission in life to the point where I almost want to stop my career is to keep my child engaged and entertained and offline, you know, like, however I can try to do that, like being present and not just being on my phone.”
  [13:03]

4. The Burden of Constant Connection

[14:16 – 16:13]

• Pete expresses discomfort at being expected to reply to endless texts and audio messages, preferring deeper, less transactional communication.
  • Pete: “Stop texting me. You’re all jacked up on some energy drink and you’re firing off…”
    [14:16]
  • Natasha: “Only certain people do [audio messages]. It’s a personality type…It’s invasive.”
    [15:46]

5. Kids & The Internet: Fears and Realities

[17:13 – 30:55]

• Natasha shares her daughter uses her as “Google,” reflecting on the weird new middle ground for kids and tech.
• They commiserate about vices and quitting nicotine so as not to pass addictions on to kids.
• The conversation shifts to the perils of children’s internet exposure, especially in school settings:
  • Natasha: “None of us can save our kids from seeing, you know, double anal on the playground now because all the kids have phones…Our principal at our school was like, the sixth graders are showing the little kids porn on the playground.”
    [29:40]
• Pete’s visible discomfort and sadness highlights how surreal and difficult modern parenting can feel.

6. Cultural Anxiety, Environmental Doom, and Choosing Hope

[31:25 – 36:12]

• Discussion of Natasha’s book’s genesis after the 2016 election and the existential dread that almost stopped her from having a child.
  • Natasha: “I was like, you know what? It made me think I’m not going to have a kid. Like, I can’t be in a world where this person is the president…” [23:43]
• Pete and Natasha debate environmental doom vs. optimism:
  • Natasha: “Don’t you think it’s going to get bad?”
    [33:12]
  • Pete: “I’m like, we will figure it out. There’s going to be a way.”
    [34:13]
• The conversation closes on the idea that parenting can be a strange act of faith and optimism.

7. Traveling, Status, and Class (A Comedy of Air Travel Woes)

[39:54 – 77:28]

• Natasha recounts miserable European travel with her daughter and Moshe, riffing on everything from climbing on ruins to Ryanair misery to being “zone nine.”
  • Natasha: “My daughter…called [coach] ‘dumb class’...”
    [69:38]
• The two examine how air travel pecking orders reinforce status anxiety, self-worth, and even childhood trauma:
  • Pete: “Nice hotels are just like, ‘hello, Ms. Leggero, we have your room ready…’ you just go like, I’m being healed from my trauma. I’m not kidding you.”
    [73:59]

8. Gender, Parenthood and Later Motherhood

[82:00 – 85:47]

• Natasha philosophizes on what it means to be a woman and a mother at 50, emphasizing the little-discussed menopausal “second act”:
  • Natasha: “Women have this, like, second act and, like, what could that be?...and I don’t think people have really talked about it that much.”
• Pete highlights how honest writing about the difficulty of motherhood is healing for readers who feel isolated or “doing it wrong.”

9. Pressures of Social Media & Parenting Advice Overload

[47:29 – 48:09]

• Natasha: “Part of me getting off social media was my algorithm was only people telling me I was doing it wrong...Never say, ‘good job.’ Always say, ‘you worked really hard on that.’ And like, now my daughter...is on to me.”

10. Vices, Sobriety, and Needing to "Be a Monster" Sometimes

[97:13 – 98:33]

• Natasha reflects that a small amount of self-centeredness or assertiveness (“1% monster”) is crucial to functioning well in showbusiness and even personal life.

11. The Occult, Ghosts, and Believing in the Unseen

[98:33 – 105:12]

• Classic YMIW closing: Pete asks about ghosts. Natasha has never seen one but is open, shares a story of a cryptic “out-of-body” dream message, and discusses the spectrum between radical skepticism and openness to the mystical.
  • “Some people have talents, you know, like, intuition is a talent… some people are just more sensitive, open to that realm.”
    [105:12]

Notable Quotes & Memorable Moments

• On Parenting and Technology:
  • Natasha: “My phone will be my child.”
    [05:43]
• On Internet Virality:
  • Pete: “You’ve been…you know those old Apple commercials where they’re like, walking in a dystopian future? Those are the idiots that are like, hawk tooie girl. Like, they’re wearing, like, gray flour sack onesies. They’re all shaved. They have numbers on their eyebrows. Those are the fucking…”
    [07:11]
• On Social Media and Authenticity:
  • Natasha: “My mission in life...is to keep my child...offline, you know, like, however I can try to do that, like being present and not just being on my phone.”
    [13:03]
• On Airplane Status Anxiety:
  • Natasha: “My daughter unfortunately has flown first class before…She was like, why can’t we sit in the front of the plane?...She goes, this is dumb class.”
    [69:37]
• On Gender Parenting Stereotypes:
  • Natasha: “None of us can save our kids from seeing, you know, double anal on the playground now because all the kids have phones.”
    [29:40]
  • Pete: “I think we need me, and I think we need whistleblowers. And I think we need people that are really freaking out. I think we need everything in between.”
    [105:18]

Timestamps for Key Segments

• 03:26 — Natasha’s book, motherhood, and cover shoot story
• 05:40 — “My phone will be my child” moment
• 07:11 — Pete’s viral culture diatribe
• 13:03 — Natasha on keeping her kid offline
• 23:43 — Election night trauma and reproductive anxieties
• 29:40 — Kids and internet dangers in schools
• 33:12 — Environmental/anxiety debate
• 39:54 — Mundanities of parenting (“stop climbing on a ruin” in Europe)
• 69:37 — Child calls economy class “dumb class”
• 73:59 — Pete on hotels, status, and trauma
• 82:00 — Menopause, second acts, and women after 50
• 98:33 — On being “1% monster” to get things done
• 100:10 — Dinner with Moshe’s scientist family: astrology debate (Natasha at "51% belief")
• 101:16 — Natasha’s out-of-body dream message story

Tone & Style

• The tone is irreverent, quick-witted, occasionally confessional, and deeply self-aware.
• Both Natasha and Pete oscillate between social satire, sincere vulnerability, and playful roasting—there’s a lived-in camaraderie and comfort.
• As always, Pete Holmes steers the conversation towards the philosophical and spiritual, while keeping the banter brisk and the jokes sharp.

Closing Thoughts

An episode filled with relatable parental anxieties, creative confessions, and nostalgia, this is a rich, funny, and insightful conversation. Natasha’s candor about the weirdness of the world—and the mundane trials of being a woman, mother, and comedian—makes this a must-listen for fans of comedy with depth. Pete’s warmth and curiosity keep the episode moving, with plenty of quotables and memorable moments along the way.

Final note: Natasha does not say "keep it crispy"—but finally gives in with a laugh, embodying the spirit of the show up to the last moment.