You Made It Weird with Pete Holmes

Guest: Jimmy Kimmel
Episode: Jimmy Kimmel (Re-Release)
Release Date: October 10, 2025

Episode Overview

This special re-release features late-night host and comedian Jimmy Kimmel sitting down with Pete Holmes for a funny, candid, and often heartfelt conversation. The episode explores Jimmy's upbringing, career journey, personal anxieties, thoughts on masculinity, family, comedy, and life itself. The chemistry and shared weirdness between Pete and Jimmy make for a deeply engaging and laughter-filled hour.

Key Discussion Points & Insights

1. Opening Banter & Setting the Stage

• Jimmy and Pete exchange playful greetings, joke about the audio setup, and introduce "Dan," Jimmy's friend visiting from New Jersey.
• Notable Quote:
  "Your microphones sound really good ... the headphones are almost childish. They're toys, is what they are."
  — Jimmy Kimmel (03:09)

2. Big Heads, Heritage, and Sexuality

• Spirited discussion about head sizes among comedians and their families (“Is your wife funny?” “She’s the big head writer.”)
• Playful riff on Irish heritage and its supposed links to hard-headedness.
• The spectrum of sexuality and feeling out of place at Pride events.
• Notable Quote:
  "Maybe we're more tightly wound because we feel like we have to look cool or masculine or something in order to put our penises into vaginas."
  — Jimmy Kimmel (05:41)

3. Masculinity, Permission, and Social Anxiety

• Why men struggle to fully let loose at parades, weddings, etc.—the need for “permission” (often alcohol).
• The burden and performance of masculinity: “We achieve erections — they're achievements.” (06:12)
• Comparison to ritualistic rites of passage for boys and what becoming an adult means in modern times.
• Timestamps:
  • Spectrum/Parade: 04:28–06:16
  • Alcoholic permission: 06:50–07:11

4. Marriage, Growing Up, and Family Dynamics

• Both married young — Jimmy at 20, Pete at 22.
• How marriage forced them into practical adulthood (moving, fixing sprinklers, etc.).
• Reflection on seeing early relationships not as failures but as formative experiences.
• “The thing that really made me a man was...packing a 26-foot moving truck... and driving it from Seattle to Phoenix.”
  — Jimmy Kimmel (07:58)

5. Childhood, Parenting, and Comic Book Nostalgia

• The difference in parenting sons vs. daughters, reliving childhood through their kids.
• Boys’ induction into “the men’s group” and the lack of clear contemporary rituals.
• Comic books, toys, and how economic freedom enables childish impulses (life-size Batman busts, “masturbation castle”).
• Timestamps:
  • Rites of passage: 09:16–10:37
  • Toy nostalgia: 11:11–11:49
  • Masturbation castle: 11:49–12:03

6. Generational Delayed Adulthood & the Value of Struggle

• Extended adolescence in the current generations due to abundance of “fun things.”
• The actual benefits of video games—skeet shooting skills for kids.
• The enduring value of “origin stories” and the warmth of war stories from struggling times.
• The agony of job hunting in early career radio, the Radio & Records magazine ritual.
• Notable Quote:
  "You forget to enjoy it when it's happening ... there was absolutely nothing funny about it."
  — Jimmy Kimmel (19:18)

7. The Burden of Obligations and Scheduling Anxiety

• The dread of obligations, even fun ones (“if it's on the calendar, I don’t want to do it”).
• Relates to dread for social rituals like weekends and scheduled fun.
• Procrastination and pranking his future self with delayed commitments (like nailing bacon to the wall to eat a year later).
• Timestamps:
  • Dreading fun: 24:16–24:50
  • Bacon prank: 26:27–27:40

8. Anxiety, Identity & Late-Night Television

• Jimmy’s anxiety around trying new things and watching the starts of other people’s talk shows.
• The pressure and anxiety of hosting live TV.
• The difference between live, unedited shows and the safety net of post-production.
• Discussion about the evolving authenticity in comedy audiences crave today.
• Timestamps:
  • Late night anxiety: 28:27–30:54
  • Talk show authenticity: 31:10–33:45

9. Comic Pranking, Sensitivities & Boundaries

• Era of pranks: The morality of pranking, the Paris Hilton plane stunt, and difference between cleverness and cruelty.
• Love for long-term targets (Aunt Chippy) and the joy of milking reactions (“ringing one more drop out of a bar rag”).
• Notable Quote:
  "There's nothing I like better than ringing one more drop out of a bar rag."
  — Jimmy Kimmel (38:39)

10. The Heaven/Hell of Talk Shows & Comedic Pressures

• The push-pull of daily creative output—sometimes "heaven," sometimes "have I gotten what I wished for?"
• The unique anxiety of segment-driven comedy (“You have seven minutes to be funny — in 30, I can be funny, but seven?”).
• The value of embracing failure and mistakes on air.
• Timestamps:
  • Segment pressure: 42:01–43:14
  • Embracing mistakes: 31:10–33:45

11. Faith, Upbringing & Meaning of Life

• Both raised Catholic; view church as a foundation for morality and community, if not literal faith.
• The golden rule, Jesus’ “love one another,” and resistance to red tape in religion.
• Pete presses Jimmy on the greater meaning of life — Jimmy references James Taylor’s “The secret of life is enjoying the passage of time.”
• Notable Quote:
  "The secret of life is enjoying the passage of time. And that is something that eludes me in general."
  — Jimmy Kimmel (76:37)

12. Mortality, Guilt, and Being a Good Person

• Jimmy’s honest discomfort with wealth, feeling he “should give more of my money to people” (very Catholic guilt).
• Discussion about performing good acts for intrinsic vs. extrinsic/reward-based reasons.
• Memories of childish fear of adults and the lasting effect of scary priests in Catholic upbringing.
• Philosophical reflections: Afterlife beliefs (“If you're a positive force, your energy goes on as part of a symphony...”) but ultimately accepting not knowing.
• Timestamps:
  • Wealth guilt: 83:09–83:46
  • Afterlife musings: 78:28–79:24

13. Comedy as Coping & Family Influence

• Early experiences making classmates laugh, getting hooked on audience reactions.
• Family wit and mischief, particularly his grandfather and their legendary pranks (putting out cake candles with wet hands).
• The joy in the “predictability” of certain types of humor (e.g., people walking into glass doors).
• Notable Quote:
  "Comedy's supposed to be based on surprise, but it's the predictability is what kills me."
  — Jimmy Kimmel (60:13)

14. Obsessions: Charging Phones, Limes, & Mundane Details

• Deep dive into Jimmy’s organizational anxiety — obsessive about plugging in devices, taking photos of his parking spots, and buying limes in bulk at Costco.
• Amusing tangent about lemons in Mexico and decaf coffee in South America.

15. Fame, Money, and Shyness

• The upside to fame: makes the world “a small town” and breaks the ice for a usually shy person.
• The relief of not worrying about money after years of genuine financial hardship.

16. Lightning Round (Weird Questions & Final Thoughts)

• Last time Jimmy cried: On-air talking about David Letterman retiring—his “nightmare” moment
• Fights: Many as a Brooklyn kid; had a dedicated “fighting shirt”
• Sleep: Has narcolepsy, can fall asleep instantly, sometimes even driving
• Hardest laughter ever: Childhood go-kart collision, church/funeral laughs, and legendary family fights
• Favorite parent: Deeper attachment to mother, more chumminess/video texts from father (who sometimes sends him photos of his own bowel movements!)
• Pete’s closing: You’ve hit the “hard laugh bell” so many times, this is one of the funniest episodes.

Notable Quotes & Memorable Moments (with Timestamps)

• On Pranking & Family:

  "There's nothing I like better than ringing one more drop out of a bar rag. Like, just when you think there's nothing left, you get one more."
  — Jimmy Kimmel (38:39)

• On Obligations:

  "If it's on the calendar, I don't want to do it. ... It's terrible. It's a great, terrible way to live."
  — Jimmy Kimmel (24:16)

• On Struggle & Career:

  "You forget to enjoy it when it's happening ... there was absolutely nothing funny about it."
  — Jimmy Kimmel (19:18)

• On Money & Fame:

  "I do like that part about it because I am generally very shy. ... The idea that that ice is broken with almost everyone I meet is a great relief for me."
  — Jimmy Kimmel (84:07)

• On the Meaning of Life:

  "The secret of life is enjoying the passage of time. And that is something that eludes me in general."
  — Jimmy Kimmel (76:37)

• On Being Good for the Sake of It:

  "There's something wrong with being a good person so you'll be rewarded for it in the future ... that kind of defeats the purpose."
  — Jimmy Kimmel (79:11)

• On Church Humor:

  "Church laugh is really good. Funeral laughs, crazy."
  — Jimmy Kimmel (110:45)

Important Timestamps for Segments

• 03:13 – Microphones & comedy head sizes
• 04:28–06:16 – Sexuality, Pride, and masculinity
• 07:38–08:47 – Getting married young and growing up fast
• 09:16–10:37 – Rites of passage and masculinity
• 11:49–12:03 – Masturbation castle and man-childhood
• 19:08–20:07 – The agony of job hunting in early career
• 24:16–24:50 – Fear of obligations (the “calendar” quote)
• 26:27–27:40 – Future Jimmy’s problem: eating year-old bacon
• 31:10–33:45 – Talk show authenticity and parodies of parodies
• 60:13–60:22 – Laughing at predictable behavior
• 76:37 – The secret of life
• 79:11–79:24 – Afterlife musings
• 83:09–83:46 – Wealth guilt
• 110:45–112:57 – Church and funeral laughs

Episode in a Nutshell

This episode is a warm, wide-ranging, and exceptionally funny conversation that dives deep into Jimmy Kimmel’s quirks, anxieties, memories, and comedic worldview. It's rich with stories about family, friends, pranks, and the pains and triumphs of life in show business. Pete and Jimmy are open, self-deprecating, and philosophical, making it as meaningful as it is hilarious. If you want rare insight into the mind and heart of a late-night legend—complete with tales of limes, prank wars, and the meaning of life—this is a can’t-miss episode.

Ending Catchphrase:
Pete: "And we end the podcast with the guest saying, keep it crispy. It's just the thing."
Jimmy: "Keep it crispy." (117:52)