You Made It Weird with Pete Holmes

Guest: Moshe Kasher (#2, Re-Release)
Release Date: July 2, 2025

Overview

In this much-beloved re-release of their second conversation, Pete Holmes welcomes comedian and writer Moshe Kasher back to You Made It Weird. The episode quickly dives into their signature blend of deep personal reflection, Jewish identity, philosophical musings, and relentless, often absurd, comedians' riffing. The conversation weaves through religion, trauma, humor, relationships, the prison-industrial complex, and the power of embracing one's secret (and public) weirdness. The chemistry between Pete and Moshe makes for both gut-busting laughter and poignant, vulnerable truths.

Key Discussion Points & Insights

1. Catching Up & Callback Riffs

• Early Laughter & In-Jokes:

  • The episode opens with Pete and Moshe referencing their previous "fuck guy" conversation, which fans still approach Moshe about at shows (08:02).
  • Extended, hilarious bits riffing on impressions—especially "racist Stephen Hawking," bad Schwarzenegger impressions, and video game nostalgia (10:00–13:54).

• Jewish Stereotypes and Gallows Humor:

  • Playing with sensitive topics ("Scrooge McDuck is Jewish," "did you get the secret call on 9/11") as a way to deflate hate and distance themselves from, rather than endorse, stereotypes (25:45–30:43, 29:03–30:43).
  • Moshe explores the purpose and power of lampooning stereotypes—to reveal their absurdity and rob them of power.

2. Moshe’s Upbringing and Family History

• Deaf Parents and Complex Jewish Lineage:

  • Moshe shares about being raised by two deaf parents, a father with a wild artist-to-devout swing, and a family roots in Hasidic Judaism (24:07–35:12).
  • Describes the duality of his upbringing—secular life in Oakland, CA mixed each year with immersion in a rigid Hasidic community in New York (73:20–77:49).

• Bar Mitzvah Trauma & Religious Shame:

  • Moshe details the alienation and fear of being "found out" as not truly religious, faking yeshiva attendance, and how childhood shame lingers into adulthood (90:49–99:49).
  • Shares a pivotal story of owning his difference—returning to New York as an adult with long hair, letting go of shame, and truly "becoming a man" (118:45–121:37).

• Memorable Quote:

  • “If you could go back to the place of your deepest childhood trauma and have it physically manifested on your head… I took a deep breath and let my hair spill down onto my shoulders like Samson. That day, I became a man.” —Moshe Kasher (120:45)

3. The Function & Necessity of Humor in Facing Pain

• Gallows Humor through History:

  • The historical roots of Jewish humor as a survival tool in times of oppression—including jokes in concentration camps and Moshe’s own family’s legacy of “some laughter, some tears.” (36:24–39:10)
  • Pete relates personal experiences with performance anxiety and using pain as fuel for creativity and personal growth (35:15–36:08).

• Notable Exchange:

  • “Anything you ever laugh at, you’ll never be ashamed of again.” —Moshe recounting an AA speaker’s wisdom (113:08)

4. Deep Dive: Law, Justice, and The Prison System

• Religious Law vs. Secular Law:

  • Moshe explains his rabbi brother’s research: religious law’s obsession with righteousness and justice vs. Western law’s focus on victory and winning (52:06–52:43).
  • References Viktor Frankl’s Man’s Search for Meaning in discussing how, tragically, the most compassionate perished in the Holocaust camps (53:14–54:33).

• American Prisons as Modern Slavery:

  • A serious tangent on the racist roots and present impacts of mass incarceration in the U.S.—specifically the transition from slavery to segregation to the war on drugs and then to mass imprisonment (40:45–45:32; 45:35–48:38).
  • “The criminal justice system is a form of new slavery dressed up to look like justice.” —Moshe Kasher (43:54)

5. Intimacy, Love, and the “Wolves & Dachshunds” Metaphor

• Monogamy, Fear of Losing Freedom, and Childhood Patterns:

  • Moshe, once a self-described “fuck guy,” talks about his first real relationship (with Natasha Leggero), the difficulty of moving from transactional sex to true intimacy, and ingrained fears from his mother’s overbearing love (59:20–67:17).
  • Pete and Moshe use the metaphor of the domesticated wolf to describe the ambivalence of leaving bachelorhood for committed partnership, the nostalgia for independence, and the challenge of building a “prison” for oneself out of love and habit.

• Notable Exchange:

  • “The furthest distance in the Universe is the 12 inches from your brain to your heart.” —Moshe Kasher (59:59)
  • “Every once in a while… I miss yelling at the moon.” —Pete Holmes (69:01)

6. Religious Texts, Belief, and Cognitive Dissonance

• Questioning the Torah and Bible:
  • Pete and Moshe discuss the paradoxes in “divinely inspired” scripture, how Jews and Christians deal (or don’t) with the idea that humans wrote and redacted religious texts (82:10–86:07).
  • Touching on the Mishnah, oral Torah, and the Jewish embrace of scripture’s ambiguity (“Only a fool would believe that all of the midrash are true, and only a fool would believe that none of them are”—85:04).

7. Pain, Authenticity, and Finding Joy

• Coming Full Circle—Embracing One’s Past:
  • Moshe recounts the transformative experience of confronting his childhood fears and letting go of religious shame, while Pete celebrates humor and openness as tools for healing (121:00–121:41).
  • The value of “no secrets” and sharing your weirdness as liberation (113:42–114:21).

Notable Quotes & Moments (with Timestamps)

• Opening Bit:
  “You made it weird. You made it with. You made it weird. Oh, yeah, you made it weird.” —Moshe Kasher (00:00)

• On Jewish Humor and Survival:
  “The Holocaust says they’ve made one too many Holocaust movies. It’s almost become obscure, cartoonish... At this point, when I see a poster for a Holocaust movie, my instinct is like, oh God, they’re doing this again. But there was joking in the camps so that people could make it through the most miserable points of existence.” —Moshe Kasher (36:38)

• On Self-Acceptance:
  “Why do I care what these strangers in a shtetl in Brooklyn think? Oh, no, he’s not religious. I’m not religious. Yeah, they’re right… What are they gonna do with that information? They’re just gonna go back to life.” —Moshe Kasher (121:00–121:07)

• On Laughter and Shame:
  “Anything you ever laugh at, you’ll never be ashamed of again. I think that really resonated with me. So I think that’s why I tell jokes about any subject.” —Moshe Kasher (113:08)

• On the Divine Comedy:
  [Running “medium soup” joke—as stand-in for the arbitrary and absurd in religious/familial life, emerges repeatedly, e.g.,]
  “The question is, if there’s an all-powerful God, can he make a cup of soup that is medium enough even for him?” —Moshe Kasher (107:53)

Important Timestamps

• Moshe & Pete catch up, callback to first episode: (07:30–08:10)
• Impressions: Racist Stephen Hawking: (10:25–13:54)
• Moshe’s childhood, deaf parents, Hasidic upbringing: (24:07–35:12)
• Gallows humor & pain through laughter: (35:12–39:10)
• American prison as slavery, systemic injustice: (40:24–45:34)
• Intimacy & domesticated wolf metaphor: (59:20–69:11)
• Bar mitzvah shame & reclaiming adulthood: (118:44–121:41)
• AA wisdom: Laughter and shame: (113:08)

Tone & Style

The tone is comedic, freewheeling, and deeply honest. The episode shifts effortlessly between irreverent, sometimes dark humor (riffing on racist stereotypes, Holocaust jokes, and phone sex lines), heartfelt vulnerability (reflecting on trauma, shame, and the search for authentic selfhood), and intellectual/philosophical discussions about religion, history, and the meaning of law and justice.

Pete’s role is a mixture of supportive friend, playful instigator, and philosophical sparring partner, while Moshe oscillates between storyteller, social critic, and deeply personal confessor.

Conclusion

This episode is a quintessential You Made It Weird experience—raucous, searching, and unafraid to explore taboo or uncomfortable terrain in pursuit of understanding and, most of all, connection through humor. Whether discussing the trauma of not fitting into strict religious molds, the quirks of Jewish identity, or the profound desire to be known and loved, Pete and Moshe bring listeners laughter, insight, and reassurance that everyone’s weirdness—public or secret—is worth celebrating.