You Made It Weird with Pete Holmes

Episode: We Made It Weird #143
Date: July 14, 2023
Theme: Musical Mischief, Vulnerability, and the Weirdness of Everyday Life

Episode Overview

This special episode of "We Made It Weird" features Pete Holmes and his wife, Val, in a meandering, music-filled, and highly candid conversation. The pair riff on everything from the secret “uncoolness” of rock stars to parenting fails, all while frequently bursting into song—and spontaneous fits of laughter. The main thread through their discussion is the joy (and self-consciousness) of being vulnerably weird in front of each other and the audience, a theme made literal with Pete’s guitar in hand for much of the episode.

Key Discussion Points & Insights

1. Music as Comedy, Comfort, and Competition

• Improv Songs: Pete repeatedly improvises songs with absurd lyrics, e.g., “Have you ever seen a donkey with a dick the size of the moon?” (03:04), turning the random into musical stylings reminiscent of Neil Young or folk storytellers.
• The Hidden Vulnerability of Musicians:
  • They discuss how artists (like Guns N’ Roses and Bob Dylan) project “cool,” but in reality, musical proficiency usually comes from obsessive, nerdy practice—not the devil-may-care persona often assumed.
  • “Those are a bunch of dorks that practiced for hours every day... You can’t play that unless you’re doing scales.” (22:54, Pete)
• Rock vs. Punk:
  • The pair explore the music culture clash: earnest, technically skilled rock bands vs. punk’s proud DIY and anti-perfection ethos. Val observes punk’s anti-effort attitude as antithetical to Pete's nature, sparking discussion about inclusion and “carving out a space for yourself” even with limited skill.
  • “It’s so against your fundamental nature...you’re very like: work at your craft, hone your craft.” (33:32, Val)
• Music vs. Comedy:
  • Pete admits to a creative envy, noting the unmatched collective power of music:
  • “Music wins. When Childish Gambino is playing to tens of thousands of people...it beats movie star. Music wins.” (17:31, Pete)
  • Reflects on how rap (especially artists like Lil Dicky) blends honesty, speed, and theatricality, making it both intimidating and moving for him as a stand-up (19:09–20:41).

2. The Brave Art of Being “Uncool” & Honest

• On Coolness:
  • They debate what defines “cool” in artists—the mysterious aloofness of Bob Dylan, the vulnerability of Lil Dicky. Pete admits he struggles to relate to those who maintain an inscrutable persona:
  • “Cool people, I have a harder time...I project my values onto them and imagine they like it. But with cool people, I just can’t imagine we’d get along.” (15:14, Pete)
• Personal Honesty as a Superpower:
  • Val encourages Pete by comparing his stand-up’s self-aware openness to Lil Dicky’s raps; both use radical honesty as their signature.

3. Parenthood, Sugar, and the Shame Spiral

• Cobbler Incident:
  • Pete recounts how a night of “honking down” on peach cobbler and graham crackers triggered a wave of rage and impatience the next morning, leading to a rough patch with their daughter, Lila (49:50–53:32).
  • He discusses the shame and vulnerability of parental frustration, and how it cracks him open for deeper empathy and spiritual growth.
  • “One of my biggest fears is that there’s this rage monster in me...I realized...if I were me, I’d be me.” (53:13 & 54:56, Pete)
• Letting Go of Shame:
  • The story ends with Pete finding grace in his own flaws: he realizes he can be compassionate with himself, not just others, reframing his anger as a temporary “weather system” rather than a failing (56:00).

4. Life Lessons from Cold Plunges and Chaos

• Cold Plunge Metaphor:
  • Drawing comparisons to the discomfort of ice baths, Pete suggests that full immersion—whether in cold water or the loud, silly chaos of podcasting—can be calming (28:21–29:58).
  • “If I put my whole body in there...your brain just goes like...it leaves its post, so there is no pain.” (29:11, Pete)

5. Riffing, Jokes, and Inside Humor

• Song Parodies:
  • Throughout, Pete and Val parody classic songs and signature sounds, poking fun at folk lyrics, Guns N’ Roses’ tough imagery paired with gentle melodies, and oddball covers.
• Memorable Playful Exchanges:
  • Playful banter on “splish splash, I was taking a bath”—building absurd bridges (“I open the door and my big socky dick...was out, and everyone saw it.” (12:12, Pete))
  • Imagined British-accented rockers, riffing on “garage bands” and Apple’s GarageBand (22:44).

6. TV Obsessions and Everyday Observations

• Alone on TV:
  • Both admit to a recent obsession with the survival show "Alone," prompting fits of laughter at how contestants always leave behind families—Pete joking, “Every single one of them deserves to be cheated on. Like, that is—you’ve broken the covenant.” (44:41)
• Baking Show Letdown:
  • Pete describes the near-miss of almost being cast on Celebrity Great British Bake Off, lamenting, “Guess who they didn’t pick? So when you’re watching it...just imagine if I was there.” (47:33)

Notable Quotes & Memorable Moments

• [07:19] Pete: “God’s pronouns are thy, thou.”
• [13:05] Val (joking about Bob Dylan): “Your vagina means democracy.”
• [16:25] Pete: “Music wins... there’s no Bonnaroo for comedy. There’s a tent, like carnies. And you go in there when you’re having a bad trip, and then I’m in there being like, ‘You ever wipe your ass?’ and then they’re like, ‘Oh, this is worse!’ and they run back out.”
• [20:41] Pete: “It’s this impossible feat... marrying the music. There’s collaboration. The person who made the beat and the person who writes the song come together.”
• [22:54] Pete: “Those are a bunch of dorks that practiced for hours every day... You don’t play—that—unless you’re doing scales.”
• [25:22] Pete: “Your boy is the most at-odds-with-himself person you’ll ever know.”
• [33:32] Val (on punk music): “It’s so against your fundamental nature... you’re very like: work at your craft, hone your craft.”
• [53:13] Pete (on parenting shame): “My biggest fear is there’s this rage monster in me. And I certainly didn’t rage, but I was overwhelmed and exasperated and wasn’t hiding it.”
• [54:56] Pete: “If I were me, I’d be me.”
• [57:14] Pete (on spiritual brokenness): “When I’m broken and I turn to something... it gets in, like liquid metal, pouring through all of the cracks, getting right into me...”

Timestamps for Key Segments

• 03:04 – Improvised “Donkey” song, folk music parodies
• 06:11 – Guns N’ Roses, coolness vs. vulnerability in music
• 13:01 – Bob Dylan, rap, and projecting values onto artists
• 16:25 – “Music Wins” discussion, envy of musical influence
• 25:22 – Pete reflects on his contradictory nature & sugar highs
• 28:20 – The cold plunge metaphor for emotional overwhelm
• 33:24 – Punk music vs. perfectionism, personal taste and inclusion
• 43:27 – Obsession with the TV show Alone, parenthood, and reality TV
• 49:50 – Sugar “binge,” the peach cobbler incident, the morning hangover
• 53:13 – Parenting fail, shame, and self-compassion revelation
• 54:56 – “If I were me, I’d be me” – applying grace internally
• 57:14 – Brokenness as the gateway for receiving meaning

Tone and Style

Throughout, Pete and Val keep things playful, honest, and irreverent. Pete’s willingness to look foolish (“I’m a donkey with a dick the size of the moon!”) is balanced by genuine self-analysis and a strong thread of empathy (for others and eventually, himself). Their dynamic is affectionate, quick-witted, and deeply “weird”—in the sense of embracing the quirky, raw, and imperfect parts of life.

Summary

This episode embodies the spirit of “weirdness” as both silliness and radical authenticity. Listeners are treated to musical goofing, real talk about the anxieties of parenthood, and the often-overlooked realities behind “cool” art and artists. As always, there’s a lesson hidden in the hilarity: letting ourselves get a little “crispy” (and weird) can open us up to transformation, kindness, and maybe even a song or two about donkeys and the moon.

“Keep it crispy!” (58:49, Val)