You Made It Weird with Pete Holmes: Jake Johnson (Re-Release)

Podcast: You Made It Weird with Pete Holmes
Guest: Jake Johnson
Date: August 27, 2025
Episode Theme: The Paradox of Gratitude, Creativity, and Realness in Comedy, Art, and Life

Overview

In this wide-ranging, candid re-release, Pete Holmes welcomes actor, writer, and podcaster Jake Johnson (“New Girl,” “Self-Reliance”) for a warm, funny, philosophical, and deeply honest conversation. They dissect what it means to sustain creative drive, the bittersweet nature of success, the paradoxes of gratitude and dissatisfaction, spirituality versus reality, the truth and spin of loss, the fun and pain of the grind, and how to stay real in showbiz’s illusion factory. Packed with laughs, self-reflection, and offbeat anecdotes, this episode is a testament to sharing the “secret weirdness” that unites us all.

Key Themes & Discussion Points

I. Creative Evolution & The Podcast Game

• Origins of the Podcast and Changing Media

  • Both Pete and Jake reflect on the early days of the podcast, recorded at Meltdown Comics (01:36), and on the challenges of being “established” versus continually shiny and new.
  • Jake discusses his transition from old-school press and acting (03:13) to understanding that media now lives in short, viral clips and instant gratification.

    “The world is changing and I’m not ready for it.” — Jake (03:34)

• Pride in Podcasting vs. Chasing the Shiny New Thing

  • Pete laments the lack of marketing for established shows and how the industry wants “new.”

    “It’s not shiny, but it is established.” — Pete (02:48)

II. The Drive to Create: Gratitude, Dissatisfaction, and the Grind

• Paradox of Gratitude and Ingratitude (11:27–20:11)

  • Jake and Pete have a recurring debate: Does gratitude foster complacency or nourish ambition?

  • Jake’s take: “Less gratitude” for career fuels the work ethic and grind.

    “If you have gratitude, I start feeling complacent… But if you have ingratitude, it makes you grind.” — Jake (12:13)

  • Pete argues for “open, satisfied” drive, asking why you do what you do—so action comes from desire, not desperation.

    “Why I want to do what I have to do will make me start doing the things.” — Pete (15:21)

  • Both agree there’s a cycle: grind then enjoy “Wavy Gravy” moments—relaxation feels better after accomplishment (21:17).

III. Showbiz as the Wild West / Good Ideas Getting Stolen

• Red Dead Redemption & Stealing Gold

  • Jake and Pete riff on how creative ideas float around, sometimes getting “stolen” or popping up elsewhere (05:34–06:09).

    "You pitch it around, they pass, then a year and a half later, you see a variation with other people.” — Jake (06:02)

• Drunk History & the Otis Redding Lie

  • Classic anecdote: Jake tells a favorite, but apocryphal, Otis Redding story that led to the original "Drunk History" pilot (08:00).
  • The internet later proved his tale was “all a lie,” but moments of storytelling become origin points for new opportunities.

    “The story is that...Otis Redding’s wife…they were going to the airport…he said, ‘No matter what happens, promise me you’ll be good.’ ...And it is all a lie.” — Jake (07:15–08:01)

IV. The Value of Loss, Vulnerability, and Feeling Your Feelings

• Non-Toxic Positivity

  • Both critique “love and light” spiritual bypassing—insisting life is both dark and beautiful, and that loss is real (67:15–71:56).

    “Our business is trying to spin every loss into a win. I don’t buy it. When you lose, you lose. And it fucking hurts.” — Jake (70:10)

• On Losing and Being Honest

  • Jake champions the value of feeling loss—“Kick in the dick” moments inspire growth.

    "Without feeling that loss, you then go, what am I gonna wake up and do?" — Jake (70:40)

  • Pete draws parallels to religious stories (Christianity as learning how to lose), noting that “death and resurrection” are about embracing loss, not just victory (71:23).

V. The Death Conversation: Meaning, Memory, and "Spin"

• On Death and Its Paradoxes

  • Deepest portion: The two debate the meaning of death—oneness vs. absence (96:42–110:46).

  • Pete offers the ocean/wave/vase analogy; Jake insists a “feel-good” spiritual unification doesn’t erase the pain and finality of lost relationships.

    “He’s gone. Yes. And John Mayer is not Jerry Garcia. But it’s also great, too.” — Jake (110:42)

  • Jake shares the powerful story of his deal with his father to scatter his ashes at Wrigley Field—and not experiencing the kind of sign or presence so many hope for.

    “The reality is, when I was on the field…I waited. The thing that we said he couldn’t do because he wasn’t there.” — Jake (105:41)

VI. The Audience: Performance, Authenticity, and Who It’s Really For

• For You or For Them?

  • Jake questions the recent shift in showbiz towards “self-indulgence over audience”—citing New Orleans street performers as a better analogy for artists (124:07).

    “If we are anything…we give people a break and we entertain. And I love thinking like that.” — Jake (125:17)

  • Pete and Jake agree authenticity is key—the best work is done for its own sake AND for the connection.

    “Banging my triangle…finally someone went, ‘What is that noise?’” — Pete (126:16)

VII. Comedy, Collaboration, and Finding Joy

• On Making Each Other Laugh

  • Jake and Damon Wayans Jr.'s approach on "New Girl": improvisational, always aiming to crack up each other in scenes.

    “My whole game is I want to make the scene partner laugh.” — Jake (131:16)

• Finale: The Hardest Laughter (136:12–137:55)

  • Jake recalls his brother as the person he’s shared the hardest, longest laughs with—playing their recurring, never-to-be-started “Still Chatting” podcast sketch.

    “Every project…we’ll never start, but we’ll get into ribs…and I’ll just be like…oh, you just made this drive home amazing.” — Jake (137:42)

Standout Quotes & Memorable Moments

• On Gratitude and Drive

  • “If you have gratitude, I do start feeling complacent...[without gratitude] it makes you grind.” — Jake (12:13)
  • “Why I want to do what I have to do will make me start doing the things.” — Pete (15:21)

• On Loss

  • “When you lose, you lose. And it fucking hurts. And it should, because you lost.” — Jake (70:10)
  • “Christianity is a study on how to lose.” — Pete (71:23)

• On Realness

  • “I’m like you…I like goals and focusing on good things…but sometimes I get really overwhelmed with just how fragile we are. We’re dandelions in the cracks of the sidewalk.” — Pete (91:05)

• On Connection, Death, and Paradox

  • “The awareness that your dad was is looking out your eyes right now…your dad was a wave…the wave crests, sizzles onto the beach, gets pulled back. He’s gone. But the water, total water, is still there.” — Pete (107:33)
  • “He’s gone. Yes…And John Mayer is not Jerry Garcia. But this is great, too.” — Jake (110:42)

• On Purpose and Authenticity

  • “At home, I’m a relationship with my wife and my kids. That’s my real life. At work, I am in a relationship with the audience, and they matter.” — Jake (127:14)
  • “I always say, it’s like a bad date when someone’s doing an impression of what they think a date is…But the good date is…you’re being real. Not to be weird—it’s kind of like this.” — Pete (133:03)

Notable Segments & Timestamps

• Podcasting Origins & Media Shift: (01:32–03:34)
• Gratitude vs. Drive, Paradox: (11:44–17:27)
• Gold Mining/Stealing Ideas in Comedy: (05:05–06:09)
• Drunk History & Storytelling Origins: (06:17–08:56)
• On Death, Loss, Spiritual Bypassing: (67:15–76:36)
• The Wrigley Field Ashes Story: (101:43–107:02)
• Debate: Are We Here or Gone? Paradox: (108:44–110:42)
• Art and Audience—Who Is It For?: (124:07–127:35)
• Comedy and Joy: Jake’s Hardest Laughter: (136:12–137:55)

Tone & Style

• The tone is candid, irreverently philosophical, sometimes raw, and always honest—full of rambunctious bits, but also real emotional depth.
• Both Jake and Pete openly challenge each other, “debate club” style, but never lose the heartfelt friendship at the core.
• Despite existential themes—death, loss, the void—the conversation remains affirming, full of playful sidebars and genuine laughter.

Recommended for:
Fans of comedy with depth, artists wrangling with meaning and legacy, anyone seeking an open-hearted, unpretentious conversation about life, loss, and the weird business of making people laugh.

Final Sign-Off:
The episode closes with Jake’s varied renditions of the show’s catchphrase, “Keep it crispy,” in character—from “New Girl” to “Self-Reliance”—ending with Pete’s proclamation:

“Best keep it crispy ever.” — Pete (138:21)

For more, stream or watch Jake Johnson’s “Self-Reliance,” listen to his podcast with Gareth Reynolds, and follow Pete Holmes for more shows and episodes at PeteHolmes.com.