You Made It Weird with Pete Holmes

Episode: Gary Gulman #3

Date: September 20, 2023
Host: Pete Holmes
Guest: Gary Gulman

Overview

In this deeply personal, hilarious, and reflective third appearance, Gary Gulman returns to "You Made It Weird" for an episode devoted to the secret weirdness of life, family wounds, creativity, comedy culture, and the subtleties of New England upbringing. Pete Holmes and Gary, both renowned for their honesty and warmth, share stories about their evolving relationships with their parents, discuss Gulman's acclaimed memoir "Misfit," and peel back the layers of what it means to be original––and to hope for unconditional acceptance. The episode is filled with signature improvisational riffs, philosophical tangents, and emotionally resonant moments on vulnerability and the artistic life.

Key Discussion Points & Insights

Comedy Beginnings & The Boston Scene

[07:08–18:52]

• Pete recounts seeing Gary perform as a young aspiring comic in Boston. Seeing Gary’s unique, non-aggressive style made Pete realize there was room in comedy for originality, not just brash personas.
  • Pete: “When I saw you, I was like, oh—oh. Like, you can come up with that. You don’t have to be that hot.” [08:15]
• They reflect on how the Boston scene was dominated by aggressive, blue-collar-style comics, but there was also an influence to "first be original" from legends like Barry Crimmins, Bobcat Goldthwait, and Steven Wright.
• Discussion on how being original often set them back with audiences conditioned to expect loud, abrasive comedy, but ultimately enabled longevity and distinction.
  • Gary: “You don’t have to sound like any of these guys... all I had to do was, well, I don’t have anything about being arrested for drunk driving. I don’t have anything about hating my wife.” [09:38]
• Analogy of comic clones: “photocopy of a photocopy of the originals” (Chris Gethard).

The Challenge of Earnestness & Family Dynamics

[11:10–22:37]

• Comics often misread as sarcastic by cynical New York audiences; struggle to express genuine affection or enthusiasm on stage.
  • Gary: “A lot of my takes are... Well, I love this thing...[but] they laugh because they think I’m being sarcastic.” [11:29]
• Hilariously recall their parents’ motto ("What are you, gay?") as the unspoken ethos of their high school/class – a joke about the performative and limiting masculinity of the era.
• Both discuss how growing up in unpredictable, sometimes cold or chaotic family environments prepared them for the toughest club crowds.
  • Pete: “Felt a little like, you know, I'm at home with this... I can win these very irregular, unpredictable people over.” [20:41]

The Drive for Parental Approval & Childhood Lessons

[22:37–35:14]

• Both comics reveal deep-seated childhood wounds and ways these shaped their hunger for attention and need for affirmation, especially from parents.
  • Gary (on family hierarchy): “The pecking order in my home was anything on television, anyone calling on the phone to my mother, then maybe me.” [21:48]
  • Stories about Gulman’s father making him repeat a grade for potential sports advantage, and the subtle traumas of unmet parental expectations.
  • Riff on Malcolm Gladwell: admiration for his writing but outrage at Gladwell’s dismissal of stand-up as easy—“He has no respect for stand up comedy.” [23:41]
  • Pete uses Gary’s story as a segue into the need for creative witnesses—people to see and validate your journey (“looking for a reporter at Waterloo Station,” a nod to the Bourne series).

Navigating Artistic Families & Writing Memoirs

[35:14–50:36]

• Gary discusses writing "Misfit," his mother’s reaction, and the uniquely Jewish maternal skepticism and botism.
  • Gary: “Her immediate response to me handing the book was, ‘Who’s the publisher?’” [38:24]
  • The difference between reactions from his wife’s family (“We are blessed”) vs. his mother’s nitpicking and undermining.
  • Pete shares his own journey of making peace with his mother, recognizing how both were “golden boys of single mothers.” [34:30]

Recognizing Family Limitations and Setting Boundaries

[50:36–60:36]

• Sade (Gary’s wife) offers critical wisdom—don’t expect deep psychological conversations from someone with a simple, literal perspective; adjust your expectations accordingly.
  • Gary, about his mother: “She knows good, bad, like, dislike. Pretty, ugly... You are bringing in 30 years of therapy... all she knows is that she didn’t like your hair.” [53:36]
• Both discuss strategies for seeking validation, disappointment with “fact-checking” families, and the persistent hope for emotional acknowledgment that rarely comes as desired.

The Pain and Acceptance of Parental Shortcomings

[55:16–104:24]

• Pete discusses the Byron Katie concept: “For me to be safe, I need my father or my mother to understand and see me in a way that I understand being understood and seen. Is that true? It's absolutely not true.” [104:10]
• Sade/Val’s view: Some parents’ neutral or evasive comments are their version of “I love you” (“Was that programmed?” or “I would never want to hurt you”).
• They debate whether their parents “did their best,” or simply defaulted to inertia and never pursued growth, contrasting that with the host/guest’s own self-development efforts.
  • Gary: “If you're a doctor, you have to keep up with [new] information... yet as a parent, not doing any of the things to become a better parent. And everybody would say they did their best.” [98:02]
• Acceptance comes from recognizing limits—sometimes it's healthier to limit contact rather than seek impossible closeness.
  • Gary: “I don't have a lot of time for them anymore.” [101:04]

Memoir Writing, Family Fact-Checking, and Storytelling Truth

[66:10–86:17]

• Both discuss the anxiety of family members reading their books and fact-checking stories.
  • Gary: “I could have gone harder. It could have been worse. Just be grateful.” [67:21]
• Pete references the Anne Lamott quote: “If people don't like how you wrote about them, they should have been kinder.” [67:25]
• The creative tension between literal truth and emotional or storytelling truth.

Creative Inspirations & Joy-Stealing Family Members

[80:17–85:10]

• Gary recounts childhood moments when his self-esteem or joy would be undercut by family members (“joy vultures”).
  • Gary: “There were a number of things... but that one was a real, like, holy, I'm not the same as I was before he said that.” [81:52]
  • Stories about getting no recognition for big achievements; family never matches enthusiasm.
• They riff on "fourth wall them"—don’t always engage combative audience members/family; sometimes talk “to the heavens” instead.

Parenting, Mr. Rogers, and Generational Healing

[88:52–107:44]

• Pete and Gary reflect on parenting, delight, and unconditional love, using Mr. Rogers and Father Greg Boyle as inspirations.
  • Pete: “We are like children drawing bad crayon drawings and God puts them on the fridge.” [90:09]
  • Gary: “That's what they never tell you about being a parent, is that it's important... to enjoy them.” [88:52]
• Stories about forgiving parental shortcomings, wanting their kids (or themselves as kids) to feel safe, loved, and accepted. Pete shares the repeated affirmation he gives his daughter: “You’re good, you’re safe, you’re loved.” [105:59]
• Riff on religious and cultural upbringings; the “Don’t be like that” energy and differences among Jewish/Christian family cultures.

Humor and Childhood Riffs

[116:33–121:06]

• Gary shares his hardest or most joyful laughs as a kid, highlighting the comedic genius of his childhood friend, Billy Mamion (“Did your dog make it?”) [119:33], and the simple pleasures of kids' jokes and camp culture.
• Pete and Gary riff on kids' pool jokes (e.g., “Thank you for coming to our ool…” [120:12]) and dissect the deeper comic structure of such childhood humor.

Notable Quotes & Memorable Moments

• Pete (on Gary's originality):
  “When I saw you, I was like, oh—oh. Like, you can come up with that. You don’t have to be that hot.” [08:15]

• Gary (on distinguishing himself in comedy):
  “There was this vibe... with the Hippocratic oath, first do no harm; theirs was first be original.” [08:57]

• Gary (on family hierarchy):
  “The pecking order in my home was anything that was on television, anyone that was calling on the phone to my mother and then maybe me.” [21:48]

• Pete (re: seeking validation):
  “For me to be safe, I need my father or my mother to understand and see me in a way that I understand being understood and seen. Is that true? It's absolutely not true.” [104:10]

• Gary (on his mother reading his memoir):
  “Her immediate response to me handing the book was, 'Who’s the publisher?'” [38:24]

• Gary (on lesser compliments):
  “You sucked that lucky feeling right out of me.” [82:54]

• Pete (on unconditional love):
  “We are like children drawing bad crayon drawings and God puts them on the fridge.” [90:11]

Timestamps for Important Segments

• [07:08] – Memory lane: Pete’s first impression of Gary on the Boston scene.
• [11:10] – The challenge of earnestness in comedy audiences.
• [22:37] – Childhood wounds and drive for affirmation.
• [23:41] – Gary's Malcolm Gladwell grievance.
• [35:14] – Navigating memoir writing and family reactions.
• [50:36] – Learning to accept limited parental understanding.
• [67:21] – How to respond to family critiques of memoirs.
• [80:17] – Joy-stealing family moments and resilience.
• [88:52] – Parenting, delight, and the legacies of love.
• [104:10] – Acceptance mantras: Letting go of the hope for full understanding.
• [119:33] – "Did your dog make it?" — Gary's childhood laughing fit.
• [120:12] – The “ool” joke and nostalgia for juvenile comic wit.

Tone & Style

• The episode is a freewheeling, digressive dialogue—switching between sharp comedic riffing, soulful honesty, family systems, and comedy shop talk. Both men communicate with a blend of wit, self-effacing vulnerability, and philosophical curiosity.

Final Thoughts

This episode is essential listening for anyone tracing the overlap between family-of-origin wounds, artistic creativity, and the earnest hope for recognition in adulthood. It explores the generational limitations of parents, the imperative and the pain of being unique, and how, for comedians especially, deep family weirdness is as much a gift as it is a challenge. If you love comedy that’s as introspective as it is side-splitting, and if you’re interested in the “why” behind our secret weirdness and desire to be seen, this is an all-timer.

Gary Gulman’s memoir Misfit is available now. Sign-off catchphrase: "Keep it crispy!" [121:38]