Transcript

Gary Gulman (0:00)

You made it with. You made it with. You made it with.

Pete Holmes (0:04)

Oh, yeah, you made it weird.

Gary Gulman (0:08)

Yes, you did.

Pete Holmes (0:12)

You made it weird with Pete Holmes. What's happening, weirdos? This is the return of Gary Goleman, his third time on the show and by far it's my favorite appearance of his. He is one of the best stand up comedians to ever do it. He. He's also one of the best writers in the world and he's written an incredible book called Misfit which is available now. I'm currently reading it. It is heartfelt, it is insightful, and it is deeply, deeply funny. It's as funny as his standup, which is an incredible achievement. So reading it is kind of like having a personal Gary Goleman standup show in your living room. So check it out. It's incredible, honestly. Misfit by Gary Goleman. I have a couple things. I have a couple things to plug up top too. Let's see. I'm gonna be at Largo in Los Angeles this month on Saturday, October 14th. Go to largo-la.com for tickets to that. I'm also going to be in Salt Lake City after that. Bloomington, Indiana. Those will all be on peteholmes.com Hope to see people out. Thanks to everybody who came out in Raleigh. Raleigh, am I saying that correctly? Raleigh. So tour dates are all@peteholmes.com and you guys know I only ads for products that I actually use and actually love. And I actually was just writing. Actually a lot of actuallys. Actually I was just writing and I was rocking my latest Pete's Pick run. Don't walk to this one. This app is brought to us by our friends at Brain fm. So I was sitting down to write, to work, and how am I going to cue my brain that it's time to sink in, to settle in and get in that flow state? Well, turns out music is a huge, huge part of that. And Brain FM has been how I get that into my daily creative routine for years now. And I'm so happy to be partnering, partnering with them. Every morning I sit at that computer behind me, I throw on these headphones, hit focus on Brain fm. On the app, I hit focus, I hit creative flow. Lo fi is my favorite genre and boom, I'm in the pocket and ready to work, create and focus. Without this specially designed lyric lesson flow state scientifically dialed in music, I find it so much harder to complete tasks. I procrastinate. I have a hard time meeting deadlines. But with Brain fm, I'm signaling to my brain literally that it is time to get things done. And it works. What is it? On the surface, Brain FM seems like an app that gives you the perfect background music for creative work, study, reading, meditation, relaxation and sleep. And that's true. But it's incredible music. It is to work, read, meditate to. But under the surface, it is so much more than that. Brain FM's composers work hard to create amazing sounding music that doesn't distract and uses their patented audio technology to boost your mental states. On demand audio signals get your brain dialed in. It's incredible. Brain FM's scientists and composers add patterns to their music that change the patterns in your brain, creating increased blood flow and electrical activity in your brain and increasing focus in as little as five minutes. Regular music is designed to be distracting, so you're constantly being interrupted, having to skip songs that are pulling you out of that flow. But not with Brain fm. Sc stop. Stop the skipping. Brain FM has a wide variety of sounds and genres, from natural soundscapes to lo fi electronic music. To get you in that zone almost immediately, but without having to pick the perfect playlist, it takes no thought. I never skip songs. I love them all. They help me dial in. And it's science backed. Brain FM actually has the scientific research to back up their claims through close collaboration with neuroscientists and a wide array of field experiments and testing. But even better, their music is made by not made by computers instead, multi instrumentalist composers. That way the soundscapes on Brain FM still have the warmth of real people. So give it a try. It's a huge part of my routine, has been for years. Great way to support your brain and support the show. Go to Brain FM. Weird. To get 30% off one year of Brain FM and start getting more done with less effort and unlock your best self on demand. Experience the difference that the right music can make in your life. Brain FM. Weird. Support the show. Support. Support your noodle. Also, I, for years, years, decades never washed my hair. Hate shampoo. I hate looking like a bale of hay that just got out of the dryer. Crispy, hard to control, horrible looking hair. So I just didn't wash it until Kat, my hairdresser, she was like pete, this is disgusting. You need to wash your hair. Yuck. I was with her. I know. I just didn't know a better way than. Thankfully modern mammals has come to the rescue. It's the only shampoo that's like a non shampoo that somehow cleans your hair so the comb goes right through it. Super clean, but leaves it perfect. It's not going to frizzle it. It's not going to fry it. You're not going to have to wear a hat for three days or hope no one takes your picture. You get a perfect hair day on demand. It has structure. It still has some of its natural moisture. It doesn't dry it out and it stays in place and looks incredible, giving your hair that wave, that flow that I am looking for after a wash. It looks like how my hair used to look if I wash it with regular shampoo and waited four or five days. But now I can have a perfect hair day just whenever I want on command. Now my hair regimen is the opposite of what it used to be. I used to not wash it when I wanted to have a good hair day. Now I use it. Modern mammals when I want to have a good hair day. So over 40,000 guys have switched to this instead of traditional shampoo. You got to see the reviews for this product. They're insane.

Summary

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]