You Made It Weird with Pete Holmes

Guest: Jay Jurden

Release Date: June 25, 2025

Episode Overview

This episode features comedian Jay Jurden in a wide-ranging, quick-witted, and candid conversation with Pete Holmes. Together, they dive into comedy craft, fashion, masculinity, queerness, adolescence, sexuality, X-Men, spirituality, and the universal human need for connection and self-acceptance. Both comedians share deeply personal anecdotes alongside cultural observations, all with a spirit of curiosity, warmth, and irreverence.

Key Discussion Points & Insights

Fashion, Identity, and “Ugly Shoe” Trends

• Gorpcore and Fashion Co-Option

  • Jay and Pete discuss the rise of “gorpcore,” where outdoor and utilitarian clothing becomes trendy in streetwear, and how fashion cyclically appropriates workwear like carpenter pants.
  • Jay: “There is this beautiful sort of like event horizon that happens with what I kind of just call unassuming white guys and fashion... you want what you want. I want like any kind of unassuming older white guy to have like a happy fashion accident.” (03:00)

• Color and Perception

  • Viola Davis’s yellow dress becomes a springboard for discussing how fashion, color, and skin tone intersect with cultural perceptions.

Stand-Up Comedy Craft

• Comedy Styles and Overwriting

  • Jay explains his tendency to overwrite, then scale back jokes for optimal laughter—a trait he shares with other punchline-focused comics.
  • Pete admires Jay’s “Gatling gun” of jokes and how he brings audiences beyond surface premises:
    • “Most specials I watch and I go, that’s it? ... When I watch you, I’m like, oh, this dude, you figured it out.” (08:18)

• Inspiration from ‘Crashing’

  • Jay credits Pete’s work on the show “Crashing” as formative in his early NYC stand-up, paralleling his own journey.
    • “You as a character on Crashing, and then also as a comedian... if I ever get the chance to tell people—so then when I did Corden and we met, I was like, that’s right, enjoys it.” (09:34)

• The Quirks of Late Night

  • They reflect on the complexities and freedoms of doing stand-up versus panel, the differences in censorship, and the pressure of late-night TV.

Body Image, Sexuality, & Media

• Hollywood Beauty & “Rat Summer”

  • Jay and Pete joke about discourse around unconventionally attractive leading men, how handsomeness, “bird face” (Ryan Gosling), and unique features become desirable.
  • Jay: “Now, do you remember what happened? ... there was rat summer. So every leading man was—they were like, these guys kind of look like rats.” (06:18)
  • The discussion drifts into the eroticization of “the interesting,” and the recurring theme of “dead hot”—the allure of former stars, old porn, and nostalgia.

• Secret Adolescent Sexuality

  • They swap stories of childhood and teenage experiences of horniness, longing, shame, and makeshift erotica—Playboy hidden in the bed, History Channel’s “History of Sex,” comic book characters dressed provocatively.
  • Jay: “My argument in regards—and connected to that is—that’s also why some people still love tan lines. Some people still love amateur stuff... that’s why people are still looking at the classics.” (24:27)

• AI Porn vs. Human Connection

  • Pete and Jay express discomfort with AI-generated sexual images, noting the enduring erotic power of real, flawed, and even “gone” people.

• Queerness in Pop Culture & Trickster Archetypes

  • An exploration of how queer energy, crossdressing, and ambiguity have appeared as “trickster” elements in myth and pop culture—Bugs Bunny, Loki, Little Richard, Divine, Prince.
  • Jay: “So that devious sort of duplicity, secretive nature... every trickster deity is still connected to the way they look at the devil currently now.” (34:15)

Comedy, Vulnerability, and Community

• Male Loneliness & the Need for Intimacy

  • Pete observes the persistent loneliness many men face, the cultural barriers to male-male emotional connection, and the ways toxic online communities have filled the void.
  • Both reflect on their own adolescent and adult need for homosocial closeness, the “male loneliness epidemic,” and the value of nonsexual, soul-bonded friendships.
  • Jay: “If you have a relationship with someone who you care about and you don’t have sex, but you do have moments where you go, I love you so much... that doesn’t exist as much for guys, young guys right now.” (60:30)

• Homosociality, Initiations, and Shame

  • They dissect the awkward rituals of adolescence—youth group meetings about “lust,” locker-room bravado, even hazing rituals like “Limp Biscuit”—and frame them as proof of societal attempts to “forged by the fire... and still follow the rules.” (50:36)
  • Pete: “You can go into the fire and come back. ... You won’t be tricked by the gay ass, but you’re not scared of him.” (50:52)

Fluidity & Acceptance in Sexuality

• Queer, Bi, “Homo-flexible” Identities

  • Jay talks frankly about his bisexual identity, open marriage, and the expanding definitions of masculinity and queerness among gay men—“the coldest bi’s” and “homo-flexible” as evolving terms.
  • Jay: “For a lot of gay guys... sometimes jerking off or giving a blowjob, it feels very much like a handshake... it’s just skin, we’re kind of just being naked together and everyone's destigmatized.” (112:05)

• Fire Island and Sexual Norms

  • They illustrate the open, communal, and sometimes chaotic sexuality in contemporary queer spaces (like Fire Island), contrasting the more guarded, rule-bound dynamics of straight couples—often with great humor.

Spiritual Reflections & The Meaning of Life

• Entropy as Oneness
  • Jay eloquently ties his spiritual view to the concept of entropy:
    • “There is a beauty in entropy... at the end of all this... I will be reduced back to whatever components and elements I came from... It’s not nothing, it’s everything—but just in such tiny little parts that we're going to be spread out amongst it.” (117:45–119:20)
• Universal Connection through Service
  • Jay reflects on his mother’s loving, inclusive form of Christianity, rooted in service, and the value of enjoying embodiment:
    • “Of course my mom’s God is real ... serving people while you’re here is such a beautiful and selfless act...” (121:41–124:39)

Notable Quotes & Memorable Moments

• On Saturn Returns in Fashion:
  “There is this beautiful sort of like event horizon that happens with what I kind of just call unassuming white guys and fashion...” —Jay (03:00)

• On Adolescence & Sexuality:
  "I can still remember. I was a freshman. There was a senior girl. She wore a T-shirt... at that point, you’re like, forget it." —Jay (43:30)
  “I was hard 70% of high school.” —Pete (43:19)

• On Comedy Craft:
  "Most specials I watch and I go, that’s it? ... When I watch you, I’m like, oh, this dude, you figured it out.” —Pete (08:18)
  “I have a tendency to overwrite... Let me scale it back to peak laugh. But I have more if you ever want it.” —Jay (07:55)

• On Tricksters and Queerness:
  “So that devious sort of duplicity, secretive nature... every trickster deity is still connected” —Jay (34:15)
  “Pan was a horny goat god. He was a god of horniness... Well, that’s why they call pansexuals. That’s it.” —Jay (35:13)

• On Male Friendship and Loneliness:
  “All I was doing was competing with them and kind of like bragging ... that’s not relationship.” —Pete (66:04)
  “If you have a relationship with someone who you care about and you don’t have sex, but you do have moments where you go, I love you so much... that doesn’t exist as much for guys, young guys right now.” —Jay (60:30)

• On X-Men, Mutations, and Puberty:
  “It’s connected to what we talked about earlier. It’s puberty. So a lot of X genes manifest at puberty. So you're going through the most stressful time ever.” —Jay (104:38)

• On Meaning of Life & Spirituality:
  “There is a beauty in entropy. ... At the end of all this... I will be reduced back to whatever components and elements I came from.” —Jay (117:45–119:20)
  "If we're the lens, the light that shines through us, the prism that's created, that's your relationship with the divine." —Jay (127:41)

Essential Timestamps

• Fashion & Gorpcore: [01:27–05:08]
• Comedy Craft & Influences: [07:55–10:58]
• Queer Artistry, Tricksters, and Camp: [31:23–37:20]
• Adolescent Sexuality, Nostalgia, Old Porn: [24:19–26:20]
• Male Friendship & Homosociality: [48:09–61:11]
• Loneliness, Emotional Vulnerability in Men: [65:17–69:22]
• Fire Island & Queer Sexual Norms: [112:04–116:38]
• Meaning of Life - Entropy & Oneness: [117:45–121:41]

Episode Vibes & Tone

The conversation flows with Nick Offerman-level warmth, classic Pete Holmes goofiness, and Jay’s affirming, investigatory humor. Both comedians are open about vulnerability, confusion, and desire for connection—never shying away from taboo but always centering joy, curiosity, and the fundamental weirdness of being human.

For New Listeners

If you want a masterclass in honest, progressive, laugh-filled conversation about everything from adolescent shame to comedy nerd craft, from gay orgies to the meaning of life, this episode is a wonderful entry point. Jay Jurden’s and Pete Holmes’ openness makes even the weirdest topics accessible and humane.