You Made It Weird with Pete Holmes

Episode: Jesse David Fox Returns

Release Date: April 23, 2025
Guest: Jesse David Fox (author, podcaster, comedy critic)
Main Theme: The art, evolution, and future of comedy in an age of digital disruption, authenticity debates, and AI.

Episode Overview

Pete Holmes welcomes back Jesse David Fox, comedy critic for Vulture, host of the Good One podcast, and author of Comedy Book. The episode is a sprawling, energetic dive into the nuances of comedy as an art form and how it’s adapting (or not) to cultural, digital, and technological shifts. They discuss authenticity, the repeating cycles and patterns among comedians, the impact of platforms and algorithms on comedic voices, and the philosophical questions of self-expression, artifice, and meaning. The episode’s tone is playful, self-reflexive, and deeply curious—full of both laughter and intellectual rabbit holes.

Key Discussion Points and Insights

1. Comedy, Artistry, and Perception (03:50–14:36)

• Jesse notes the challenge of being a guest vs. a host on podcasts, emphasizing the importance of taking notes and keeping track, mirroring the discipline required in both comedy and criticism (03:52).
• Pete compliments Jesse’s Comedy Book, observing that comedians are often skeptically impressed by anyone tackling comedy in book form:

  “So many comedians have gone, ‘Have you read Jesse’s book? ... It’s actually really good.’ And that has nothing to do with you. That has to do with the undertaking of writing a book about comedy.” – Pete (06:16)

• Inside comedy “baseball”: Pete recounts a joke about Kumail Nanjiani that he ultimately cut from his special out of sensitivity and concern about its interpretation, highlighting how the context and intention of humor get complicated in public spaces (07:27–09:49).

2. Stand-Up, Mediums, and the “Hotness” of Imagination (10:36–15:33)

• The duo debate the value and drawbacks of supplementing stand-up with screens or documentary footage, referencing Jenny Slate’s special as an example. Jesse feels proving the truth of on-stage stories via cut-in footage can be antithetical to stand-up’s magic:

  “There is something about the need to prove that what you’re saying on stage is true that I find antithetical to the art quality of stand up… I want to see how your brain works and how your brain paints the picture in my head, and not just being like: see, I really captured their voice.” – Jesse (12:03)

• They discuss the difference between “hot” (imagination-engaging, e.g., audio) and “cold” (showing everything, e.g., video/TV) media, with Pete noting that audio-only records like Steve Martin’s allow the audience to imagine and thus become more engaged (13:00–14:46).

3. Titles, Inclusion, and “Chef’s Reimagining” (15:33–18:45)

• Jesse muses on the challenge of titling Comedy Book:

  “I have a Google alert for comedy book. And it is almost never my book… It’s very punk rock.” – Jesse (15:53)

• They liken unique comedians (like Demetri Martin) to “chef’s reimagining” of a classic dish, highlighting how the comedy audience’s desire for innovation rises when the market is flooded with sameness (18:25–18:45).

4. The Cycle of Comedy Trends and the Impact of Audience and Algorithms (22:56–29:32)

• Repetitiveness in comedy: Jesse shares that his early excitement for stand-up faded due to the monotony of material and audience interactions, e.g., being called “Harry Potter” for having glasses by multiple comics (22:53).
• Pete observes that comedy catered to infrequent audiences led to formulaic performances; Jesse points out the shift:

  “Too much comedy or too many comedians gear their actions to people who see almost no comedy whatsoever.” – Jesse (23:47)

• Both lament how the rise of social media and algorithms is narrowing comedic voices, rewarding styles that fit platform templates rather than those arising from authentic exploration (28:25–29:32).

5. Authenticity, Performance, and the Myth Thereof (34:08–38:18)

• Jesse posits that “authenticity” in performance is itself a constructed ideal, not a natural state:

  “Authenticity is not that old of a concept… As a result, authenticity had been fetishized for decades. Even though there are people ... who would be like, ‘Authenticity is a fraud. The idea that you can be authentic: every single person gets up and puts on a shirt. You can’t not decide to put on a ... It's a performance as well.’” – Jesse (34:24)

• Discussion of self-awareness and meta-commentary in comedy—how acknowledging tropes (e.g., “every comedian has a joke about their prostate exam; here’s mine”) has become its own sign of honesty (37:07).

6. Comedy as Connection and Art—Polishing the Mirror (39:41–41:10)

• They delve into comedy’s power as a tool for near-universal communication and emotional resonance, using laughter as proof of mutual understanding:

  “Comedy is great because ... We’re not going for tears or, like, silence. We’re going for an involuntary [response]: ‘I understood you.’ So—has a real appeal to children that felt misunderstood.” – Pete (39:55)

• Jesse frames comedians as polishing a “steel” into a mirror through audience feedback, culminating in a shared experience (41:04).

7. The Threat and Banality of AI in Comedy (50:07–56:32)

• They address the current and speculative roles of AI, from joke generation to content curation. Jesse warns:

  “The dystopia ... it’s just much more boring. AI will get to the point that people use it to write their emails, and then people use AI to read that email and reply to it ... So then, as a result, AI is living a mundane life and we’re doing nothing.” – Jesse (55:24)

• Pete and Jesse agree that algorithm-driven feeds are making comedy (and culture by extension) more homogenous, less surprising, and less human (54:45–56:18).

8. Hedonic Treadmills, Mortality, and Appreciating the Present (58:56–68:13)

• The conversation widens into philosophical territory: how chasing infinite pleasure (food, sex, entertainment) doesn’t satisfy, and real appreciation comes from understanding limits—especially mortality.

  “Literally, all death informs kids’ cake. Death informs all joy—hypothetically, that is the potential that it is limited.” – Jesse (64:52)

• They discuss the human response to mortality, the (futile) pursuit of digital or biological immortality, and the meaning of “being alive” within or outside those quests (68:13–68:19).

9. Spiritual and Existential Wrapping Up (73:17–82:21)

• The episode closes on a reflection of spirituality, uncertainty, and the endless quest to “know what it is”—be it the self, consciousness, or the purpose of comedy.
• Jesse shares lines from the book’s epigraph:

  “Humor is the last stage of existential awareness before faith.” – Soren Kierkegaard
  “Comedy is to make everybody laugh at everything and deal with things, you idiot.” – Joan Rivers (84:16)

• The book’s heart, Jesse reveals, is that comedy (and writing about it) is his way of understanding and communicating how he sees the world (85:25).

Memorable Quotes & Moments (with Timestamps)

• On the dangers of comedic homogeneity:

  “Too much comedy or too many comedians gear their actions to people who see almost no comedy whatsoever.” — Jesse (23:47)

• On “hot” mediums:

  “Valley Heat podcast ... it almost ruins it because the way it comes out, you have to imagine it so that maybe you know this. That’s called a hot medium, meaning you’re engaged with it ... A cold medium is television. It just shows it to you.” – Pete (13:00)

• On authenticity as artifice:

  “Authenticity is a fraud. The idea that you can be authentic… Every single person gets up and puts on a shirt. You can’t not decide to put on a ... It's a performance as well of what they want to communicate. And it's very transparent on stage.” — Jesse (34:24)

• On audience as creative collaborators:

  “The comedian has an observation ... and through audience interaction, it polishes ... it becomes a reflection of the audience because of the audience’s response.” – Jesse (41:04)

• On AI and the end of mutual experience:

  “AI will create a feed for AI to consume and then tell you all the things it did ... The self that is the artist is being removed and the self that is the art consumer is being removed.” – Jesse (56:08)

• On mortality and the appreciation of pleasure:

  “The reason you appreciate chocolate cake is that you know that you will only have a hundred before you die ... Death informs all joy.” – Jesse (64:50)

Notable Segment Timestamps

• On cutting jokes for sensitivity: 07:27–09:49
• Philosophy of ‘hot’ vs. ‘cold’ mediums: 13:00–14:46
• Comedian market trends and uniqueness: 18:25–23:33
• Algorithmic compression of comedic voices: 28:25–29:32
• Deep dive into authenticity and performance: 34:08–38:18
• The banality of an AI-driven future: 55:24–56:32
• Mortality and the value of limits: 64:50–68:19
• Epigraph quotes and book summary: 84:16–85:25

Closing Tone and Takeaways

This episode is a meandering, deeply self-aware conversation about how comedy functions as art, how it’s shaped by and shapes both audience and performer, and how it must adapt (or not) to a changing technological environment. Pete and Jesse repeatedly circle back to the importance of self-knowledge, the inevitability of artifice, and the necessity of appreciating comedy—and life—in light of our limitations.

Final Words:

“Comedy is everything. It’s my way through to everything. Like, it’s how I understand the world. And writing about comedy is how I can communicate how I see the world… The goal is to make people, I think, appreciate comedy differently and to appreciate it as an art form in the hope of them just being able to generally appreciate things more deeply.” – Jesse (85:25)

[End of Summary]