How Gary Gulman Turned Depression Into Comedy Gold | Better in Person

Summary

Freakonomics Radio: "How Gary Gulman Turned Depression Into Comedy Gold | Better in Person"

Release Date: July 29, 2026
Host: Stephen J. Dubner
Guest: Gary Gulman (comedian, author, former accountant)

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Episode Overview

In this rich, wide-ranging interview, Stephen Dubner sits down with comedian Gary Gulman to explore how Gulman transformed his decades-long struggle with depression into a unique brand of brutally honest, deeply human, and often hilarious comedy. They discuss Gulman’s creative process, family, the intersection of mental health and humor, and the personal journey behind his celebrated HBO special "The Great Depress." The conversation is candid, funny, and full of insights into resilience, creative honesty, and the power of talking about what hurts.

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Key Discussion Points & Insights

1. Making Comedy from Pain: Gulman’s Personal and Creative Journey

• Gulman’s Background: Former accountant at PricewaterhouseCoopers, fired for expressing irreverence ("I was fired for saying, what are they gonna do, fire me?" — Gary Gulman, 03:30)
• Discovering Comedy: Began stand-up in 1993, gradually transitioning as comedy became his main pursuit.
• Transforming Depression: Gulman describes years of cyclical depression interrupting his life and career, and how coming out of a major episode revitalized his creative output.
  • “For the past seven years, I’ve had uninterrupted mental health and I've written, I think, three specials, a one person show and a... book, a memoir.” — Gary Gulman (09:04)
• The Turning Point: After recovering from a severe depressive episode, Gulman created "The Great Depress," a comedy documentary blending humor, autobiography, and mental health public service.

2. Honesty and Vulnerability in Craft

• Opening Up On Stage: Gulman initially hesitated to discuss mental health publicly. As he started, new comedic material emerged from raw experiences, like being recognized in a psychiatric hospital:
  • “You were recognized in a particularly interesting way. Right. Didn't the guy say, are you Gary Goleman or am I crazy?” — Stephen Dubner (15:28)
  • “It was so great because it's the lowest you can get...yet part of my relentless ego was like, oh, look at me getting recognized.” — Gary Gulman (15:35)
• “Fail Better”: Gulman drew inspiration from Samuel Beckett’s quote: “Ever tried, ever failed? No matter. Try again, fail again, fail better.” It became his mantra while returning to the stage post-hospitalization.

3. Balancing Mental Health and Creative Ambition

• Vigilance: Recovery is ongoing and depends on maintaining healthy habits—exercise, medication, therapy, sleep, and social activity.
  • “I need to stay so vigilant and prevent the relapse because the relapse is actually part of this entire conundrum.” — Gary Gulman (11:46)
• Financial/Logistical Barriers: Unstable finances early in his career affected his ability to access therapy and medication.

4. Making “The Great Depress”

• Process and Collaboration: After recovery, Gulman pieced together his live show at the Comedy Studio in Harvard Square, integrating stand-up with deeply personal storytelling. His manager suggested documenting it as a hybrid stand-up/biographical special, bringing in director Mike Bonfiglio and producer Judd Apatow.
  • “What if we did a hybrid of a documentary and a special?” — Brian Stern, manager (17:54)
  • “In the meeting...he said, do you mind if I ask my friend Judd (Apatow) if he would like to work on this?... and then we shot it in June. It aired in October.” — Gary Gulman (34:49, 36:02)
• Public Impact: The special has become a touchstone for people struggling with mental illness, providing language and validation for viewers.

5. The Intersection of Family, Origins, and Comedy

• Critical Household: Gulman details a loving but highly critical family environment as comedic and personal fodder.
  • “Some of the most unimpressive people, and yet so critical. It astonishes me that people this average could be so critical about every aspect of everyone.” — Gary Gulman (28:28)
• Repercussions of Memoir: Sharing family stories—like his mother’s past stealing greeting cards—led to temporary estrangement.
• Economic Realities: Gulman's upbringing in a low-income household influences his worldview, feelings of guilt, and generosity (references to Peter Singer and effective altruism).

6. Creative Process and Writing Methods

• Notebook as Creative Lifeline: Gulman reveals his densely-filled notebook, sticker-covered and crammed with setlists, ideas, and joke premises.
  • “A lot of it is just trying to make connections between things that aren’t connected.” — Gary Gulman (43:18)
• Memorization Strategies: Uses the Pomodoro method, mnemonics, and visual storytelling to memorize intricate shows.

7. Influences, Heroes, and Stand-Up Philosophy

• Comedic Influences: Jewish-American comedians like Garry Shandling, Richard Lewis, Steven Wright, as well as Carlin and Pryor. Lenny Bruce less so due to lack of personal resonance.
• On Specificity: Gulman cites Ralph Waldo Emerson: “The specific is universal,” and crafts detail-rich art that strives for deep relatability.
• Smiling and Joy in Performance: Strategic smiling relieves tension and is an authentic expression of excitement about great jokes and audience reactions.
  • “...with most of my jokes, I feel the way Springsteen must feel when 'Badlands' is next.” — Gary Gulman (27:14)

8. Resilience, Reinvention, and Self-Acceptance

• Handling Anxiety: Anxiety in sports and on stage is similar—sometimes paralyzing, but can be overcome by recalling past successes and “failing better.”
• Rediscovering Basketball: Playing basketball—a lifelong passion—became a personal therapy and part of recovery. Letting go of ego and reclaiming joy are vital.
  • “I had to come to terms with the fact that I would never dunk again...but that's also a great lesson, which is to curb your ego.” — Gary Gulman (41:51)

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Notable Quotes & Memorable Moments

• On Showbiz Hyperbole:
  "What do you have to understand about show business is the hyperbole is at such a high level that if they love you, it means they don't want to work with you, but they think you're pretty good..." — Gary Gulman (00:57)
• On Being Recognized in the Psych Ward:
  "Are you Gary Goleman or am I crazy?" — A fellow patient, relayed by Gulman (15:35)
• On Progress & Failure:
  “I had to realize, and it was a quote that I put on my bedroom wall at my mom's house from Beckett... 'Ever tried, ever failed? No matter, try again, fail again, fail better.'” — Gary Gulman (16:06)
• On his Mother’s Criticism:
  “I don't like how I feel about myself when I'm around these people.” — Gary Gulman (30:11)
• On Mental Health Public Service:
  "Part of the reason I am so vigilant about staying well is that I am concerned that I will let certain people down...who will tell me how The Great Depression resonated, how...they were able to watch it with a family member and the family member was able to understand better what it's like." — Gary Gulman (32:00)
• On Identity as a Comic:
  “I became better known...the depressed comic. But now grown beyond it to some degree. Although many people, I'm sure, still know you for that.” — Stephen Dubner (37:03)

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Timestamps for Major Segments

• [00:57] — Gulman on show business hyperbole
• [03:00] — Gulman’s background as an accountant
• [07:27] — Meeting his wife, Sade, and her role in his recovery
• [08:33] — Coming through depression; productivity returns
• [10:54] — Description of how cyclical depression derailed career opportunities
• [13:42] — “The Great Depress”: Hybrid of comedy, documentary, and public service
• [15:28] — Being recognized in the psychiatric hospital
• [16:06] — Adoption of Beckett’s “fail better” as a guiding principle
• [17:54] — Collaborating with manager and Judd Apatow to make the HBO special
• [22:05] — Anxiety before shows; comparison to sports performance
• [28:28] — Describing his critical family of origin
• [34:49] — Final steps in producing "The Great Depress"
• [42:35] — Show and tell: Gulman's notebook as his creative repository

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Memorable Show and Tell (41:20–45:52)

• Gulman presents his most recent notebook, filled with stickers and creative ramblings. He shares the process of working out jokes, e.g., the failed promise of microwaves to make toast (“Microwave popcorn button was a diversion from the microwave company's inability to get it to make toast.”).
• Punchlines often arrive spontaneously on stage and evolve over time, such as:
  • “We’ll always have bathtub suicides...Tell me they’ve outlawed dead-end jobs and loveless marriages. Then I’ll start panicking, because as long as there’s despair, we will sell toasters. The man was a psychopath.” (44:23–45:39)

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Tone and Atmosphere

The conversation is earnest, funny, warm, self-deprecating, and peppered with both stand-up wit and thoughtful reflection. Gulman’s openness about vulnerability is the foundation—he mixes dark humor with hope and honesty, while Dubner provides understanding, research-minded questioning, and camaraderie throughout.

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Useful Takeaways

• Honest discussion about struggle is not only viable in comedy; it can be a lifeline to others.
• Vigilance and structure—health routines, therapy, medication, socialization—are crucial for mental wellness.
• The process of creative reinvention often involves failure, humility, and collaboration.
• Comedy can serve as a bridge to understanding, not just entertainment.

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A must-listen for fans of comedy, mental health advocates, and anyone interested in the art of turning life's toughest moments into something universal and healing.

Transcript

[Stephen Dubner]

This episode of Better in Person is presented by ChatGPT. Put ChatGPT to work on your most ambitious ideas and projects. Download the new ChatGPT desktop app today. Hey there, Stephen Dubner. This is the third episode of a new video interview show we're making called Better In Person. Today's guest is the comedian Gary Goleman. You are going to love him, I guarantee. If you want the full video experience, go to the Freakonomics YouTube channel. It looks good on your phone, but it looks great on a bigger screen. You can also watch it on Apple Podcasts. Just search for Better in Person. But we also made this audio version for the Freakonomics feed in case you don't want to be distracted by the video we aimed. Please. As always, thanks for listening and now thanks for watching too.

[Gary Goleman]

What do you have to understand about show business is the hyperbole is at such a high level that if they love you, it means they don't want to work with you, but they think you're pretty good. If they're obsessed with you, they'd like to work with you. But if this fails, it's all over. You'll never hear from them again. And then I don't know what the next level will be. I want to chop you up in a Cuisinart and drink you like a smoothie. And that will mean that they would

[Interviewer/Assistant]

like to make your project.

[Gary Goleman]

This is Better in Person with Stephen

[Stephen Dubner]

Dubner and Gary Goleman. Gotta choose one word to describe the comedian Gary Goleman. It might be kind, which is not a word you associate with comedians very often. He's also tall, 6 foot 6, which helps make him good at basketball bank. He's also smart, he enunciates beautifully, he's got an amazing vocabulary, and he wrote a really nice memoir called Growing up awkward in the 80s. And yes, he is wickedly funny. Consider his first HBO special, the Great Depress.

[Gary Goleman]

I still see a therapist. I believe I broke him on Monday. Yeah, I was leaving his office and I was shutting the door and I heard him go.

[Stephen Dubner]

A show about one man's depression should not be funny. But this one is. And it's also deeply human. Goleman's honesty makes his fans love him even more. And now I also love him. Gary Gullman. I mean it. That's not hyperbole.

So I make this podcast, Freakonomics Radio, which is very research intensive and my producers for this show have been telling me that I need to back off, that I get over prepared and I get a Little paralyzed. So for you, I've done zero. Okay, I know your first name is Gary. That's all I got. You're an accountant, I understand.

[Gary Goleman]

I was an accountant. That was what I studied in college. So my profession is accountant. But then I've taken this side gig, starting in 1993, where I tell jokes and I wrote a book and I act occasionally, but it's just something if the accounting doesn't pay off.

[Stephen Dubner]

Did you ever do any accounting?

[Gary Goleman]

Yes. Yes. I worked for two and a half years for what is now PricewaterhouseCoopers, and I was fired for saying, what are they gonna do, fire me?

[Interviewer/Assistant]

You did.

[Stephen Dubner]

Now, I really said that.

[Interviewer/Assistant]

And

[Gary Goleman]

it's the only time that somebody has read back to me a quot and it didn't make me happy. Usually when somebody. You said this. Oh, that's really great. But this was like. And I will say this. I just said, yes, I absolutely said that. And that was that. They said, okay, well, yeah, I'm glad.

[Stephen Dubner]

I mean, I'm glad it worked.

[Gary Goleman]

Years later, the woman from HR and her husband came to my show. So all was forgiven. But it was.

[Stephen Dubner]

Was all forgiven. Are you a grievance holder or a grievance flusher?

[Gary Goleman]

I've been grinding certain axes with people over the years, and it's really something. I'm reading the autobiography of Nelson Mandela right now. One reason, because I admire him, but also, this has to be one of the most forgiving.

[Stephen Dubner]

Comic,

[Gary Goleman]

funny man. But he's gotta be, like, the most forgiving man in history.

[Stephen Dubner]

And you're thinking, what am I doing with my.

[Gary Goleman]

Yeah, what am I doing with my stupid things? Of.

[Stephen Dubner]

Do you punish yourself?

Period?

[Gary Goleman]

Question mark? Do I punish myself? No. But I have a lot of guilt over. For instance, my wife would love a bigger apartment than we have. But I see how certain people are living, and I think, well, it's not right that I should have so much more than the average person. So I think we do need a bigger place, because now I have three storage units, which is way too many. It's insane. Like, just filled with one of them is just a library, right? It's just all these books that I don't have room for, and also my childhood baseball card collection. I want to get a bigger place, but it has to fall within this range of not too ostentatious, where I would feel guilty because I read this book by Peter Singer, the most good you can do, where if you live within certain means and give away a certain amount, you can save lives. And so there's a lot of arithmetic involved in life.

[Stephen Dubner]

That was the Sam Bankman Friedman model. You remember him?

[Gary Goleman]

Yeah, but wasn't he disgraced and.

[Stephen Dubner]

Yes, he was. Yeah, yeah, yeah, yeah.

[Gary Goleman]

Such a good philosophy.

[Stephen Dubner]

It's a great philosophy. Effective altruism. Effective.

[Gary Goleman]

Effective altruism. Yes.

[Stephen Dubner]

Your wife's name is Sade?

[Gary Goleman]

Yes.

[Stephen Dubner]

How did you meet?

[Gary Goleman]

But she's not the Sade. I wouldn't have a small apartment if I was the heir to the smooth operator royalty stream. We met at the back table at the Comedy Cellar. She was visiting her friend who was a hostess there or a host. And the Comedy Cellar, the back table has. The tables are made out of slate, so people draw in chalk. And my wife, Sade, was drawing out the formula for the golden mean on this table. And also, she's this beautiful woman who knew a lot about physics and math. And so I said, wait, are you an intellectual? And she said, maybe. And then she would come in every other Friday, and I would make it so that I would work every other Friday. And then we became friends, and then we got lovers. And then, you know. And then we became lovers. I took her on as a lover. And that was in. We got married in 2020 during the pandemic. But we'd been together since 2014.

[Stephen Dubner]

Right, because when you were sick, she was.

[Gary Goleman]

Yeah, when I was sick.

[Stephen Dubner]

Yeah.

[Gary Goleman]

We had been dating for about six months, and then I went fucking crazy.

[Stephen Dubner]

Yeah.

[Gary Goleman]

And. And sometimes I would beg her. I would be like, you really got to get out of this. It's not. It's not going well.

[Stephen Dubner]

I've heard you say that in your act, that you begged her to leave you because you didn't want that for her because you were that sick.

[Gary Goleman]

Yeah, because I didn't think I would ever get out of it. But she believed, and she did. She would do research, and then at one point, she grew psilocybin mushrooms. She tried to get me into a study, and I wasn't able to get into the study. And then she just sent away from mushrooms and made them in our apartment, risking it like a felony.

[Stephen Dubner]

Wow.

[Gary Goleman]

To try and. Because she had.

[Stephen Dubner]

The statute of limitations, I'm assuming is.

[Gary Goleman]

I hope so. But the issue is that I don't think it's legal now, but they are still in tests of psilocybin mushrooms. Michael Pollan wrote that book, how to Change youe Mind. And it was. It's very influential.

[Stephen Dubner]

So I would love to talk about. If you feel like it, you're being sick. I mean, it's a lot More fun to talk about now that you're. Cause you seem awesome.

[Gary Goleman]

I feel awesome.

[Stephen Dubner]

You look great. You seem great.

[Gary Goleman]

Thank you. I'm so grateful. And everything is just so much easier from the other side. And I always used to say this. I would say if I could, if I could stop getting depressed every six to nine months and losing three to six months of productivity, I could really be good at this thing that I've put all my time into.

[Stephen Dubner]

But that's exactly what happened then, right?

[Gary Goleman]

And then finally, for the past seven years, I've had uninterrupted mental health and I've written, I think, three specials, a one person show and a. And a book, a memoir and. Yeah. So I.

[Stephen Dubner]

So your engine, your creative and comedy engine, it seems, was running as hot then before you were sick, like you'd always been hardworking, disciplined, productive.

[Gary Goleman]

Yes.

[Stephen Dubner]

But it's just like when you would get sick, then everything is back to zero or minus. Is that the way it would work?

[Gary Goleman]

Yeah, because I would lose momentum. I couldn't. For instance, if somebody had come to me in 1998 and said, we want you to make a one person show, I would say, well, that's going to take about a year. And at some point within the next six to nine months, I will fall apart and I will be out of communication and I won't be working. And then I'll spend time trying to get back on track through medication and exercise and everything else so that I wasn't dependable and I couldn't trust myself to make such long term.

[Stephen Dubner]

We worked together in, I think it was 2017, and looking back now, I think you were not well then.

[Gary Goleman]

No, no. But I would accept offers all the time because I didn't, I didn't want to. I didn't want to give in. And so I could put. I could put it together. But if you knew me, you knew I was not myself.

[Stephen Dubner]

I just remember thinking, like, he's really not very fun. Like, you didn't seem like you were having fun at all.

[Gary Goleman]

Yeah, that makes sense. I was probably incredibly anxious.

[Stephen Dubner]

I thought that was just who you were. But then I would watch your comedy and it seemed like a different.

[Gary Goleman]

Yeah.

[Stephen Dubner]

So did I just catch you on a night where you were feeling like, how many nights were there like that that you were just not.

[Gary Goleman]

I mean, it was every night from the spring of 2015 through the fall of 2017. So it was two and a half years. But also when I was working off a script of jokes, I could be much more compelling than I was in an interview and it's very hard to think when you're depressed. My psychiatrist said that a lot of people have called it faux dementia, where depressives are having a hard time making memories and keeping memories and also accessing words. And so your brain is telling you while you're in it that you'll never get out of it, and then when you're out of it that you'll never go back in it. But then you learn and you realize that, or in this case, this final case, that I need to stay so vigilant and prevent the relapse because the relapse is actually part of this entire conundrum.

[Stephen Dubner]

What does vigilant mean?

[Gary Goleman]

Exercising every day, eating right, getting enough sleep, taking on projects that keep me busy and accepting invitations. So getting out of the house and talking with people.

[Stephen Dubner]

So that all sounds sensible, but.

[Gary Goleman]

And then taking my medication every day.

[Stephen Dubner]

Oh, okay.

[Gary Goleman]

Yeah, all good.

[Stephen Dubner]

But I'm wondering, weren't you trying to do all that stuff before when you were cyclically getting sick?

[Gary Goleman]

I was not as disciplined about the exercise component.

[Stephen Dubner]

And

[Gary Goleman]

I'm lucky to have a really good therapist. I didn't always have a therapist because I. In some cases I couldn't afford it or I didn't have the insurance for the medication. So it happened. This last one happened to come at a time when I had insurance and enough money saved up that I could take a few months off to go into the hospital and get my head straight.

[Stephen Dubner]

So the special that you made. Right, we call it special. Yeah, The Great GPS Special. The Great gps. It's a great title, by the way. It's a great. It's a great. No, I'm sorry, I meant to say it's a great show, but the title is also.

[Gary Goleman]

The title was.

[Stephen Dubner]

It's a great title.

[Gary Goleman]

Yeah, thank you.

[Stephen Dubner]

What's so interesting about it to me is that it is the only hybrid. I know, like you said at some point that you are excellent at monetizing mental illness. And I think you're the world champion. Like, I can't think of anybody like Proust, if he had had the movie made or something, but he didn't really get that far.

[Gary Goleman]

Right.

[Stephen Dubner]

But. But it's an amazing piece to me because it's very funny, it's very moving, it's a great biography. It's like a documentary. It's not just a stand up, but it's also a public service announcement about how to treat mental illness.

[Gary Goleman]

Yeah. I never started telling anybody about my mood difficulties back then and I didn't start telling people close to me until this past year when I started talking about it on stage.

[Stephen Dubner]

I mean, it really is. You go through science, and some segments of it are not at all entertaining or funny. Right. So it hit me hard. I just thought it was a great piece of work, and I want to know how you made it really okay.

[Gary Goleman]

So I was recovering from my hospitalization in Massachusetts. I was living in Massachusetts, living at home with my mom.

[Stephen Dubner]

In your childhood.

[Gary Goleman]

In the childhood bedroom. I would go to this club in Cambridge in Harvard Square called the Comedy Studio. And it served two big things, which was to get me out of the house and around people and then to eventually. And it wasn't right away, but a few months after I got out of the hospital, I would go there and I would do jokes. And it became clear to me that everybody who was familiar with me would know that something was off. And also that if you didn't know me, you might think that I looked disheveled and I didn't look well. And so I felt that I had to address it. And it was most comfortable for me to address things by being funny with it. And so I would. One of the things I started saying was how I had been recognized in the psych ward, and I would say, has that ever happened to anybody? Which is kind of an old formula of comedy.

[Stephen Dubner]

You were recognized in a particularly interesting way. Right. Didn't the guy say, are you Gary Goleman or am I crazy?

[Gary Goleman]

Or am I crazy? Yeah, in a cynical word, yeah, that actually, yeah, it was so great because it's the lowest you can get, really, in my lifespan, which is to be in pajamas at 6pm and with socks with treads on the bottom. And yet part of my relentless ego was like, oh, look at me getting recognized. Like, it gave me a shot. It gave me a shot of dopamine. And also, it was just funny that he said, am I crazy? And now when I was in the hospital, I remember.

[Stephen Dubner]

But wait, then you would watch with this guy, the Office.

[Gary Goleman]

Oh, yeah, The Office would come on. The Office is always on. And the Office would come on, and I would. I don't know why I said this, but again, my ego, you know, I auditioned for that part. Jim. I auditioned for the role of Jim. And the man said. And he had to have been joking, but it was a perfect joke. He said, did you get it? And of course, the response to that, always in show business is, I haven't heard back yet. They never tell you that you didn't get it you just see the. You see the show in syndication. The interesting thing is that in the moment, I had to. I recognized if I ever get back to doing standup, if I'm ever able to talk about this, these are things that I will say and God willing, people will laugh. And so I had to realize, and it was a quote that I put on my bedroom wall at my mom's house from Beckett that said, ever tried, ever failed? No matter, try again, fail again, fail better. So fail better became my mantra. I've heard that expression has been co opted by Tech Bros. And shame on them. Because it was so helpful that even when I was bombing on stage, I could feel, no, I'm making progress. Because I'm talking about this thing in depression and treatment that isn't easy to get laughs off of. So my manager who kept in touch with me.

[Stephen Dubner]

What's the manager's name?

[Gary Goleman]

Brian Stern. And at no point did he say, when are you gonna get back on stage? But when I did start to get back on stage, he said, what if we did a hybrid of a documentary and a special?

[Stephen Dubner]

Had you done a special before?

[Gary Goleman]

Yeah, I had done three specials and it was actually the previous special that I had done that I felt was, what's a trigger? It was a trigger for this episode of depression. I don't think it was everything but the fact that I had made a special in 2014 or 15 that I felt was the best work I could do.

[Stephen Dubner]

What was that special?

[Gary Goleman]

It was called It's About Time. And it had a joke that's since gone viral about abbreviating the States. How are they gonna make a 98 minute documentary about a task that couldn't have taken more than six minutes to complete? Started off, they thought it was gonna be easy because Alabama lulled them into a false sense of security. They said, Alabama, Al. Holy crap, this is easy. We're gonna finish before they stop serving breakfast in the hotel restaurant. And they got back to abbreviate and they said, what's next? They said, Alaska, Everybody cool with Al? And it had a joke that also was very popular about me role playing with my wife. And I'm a professor, but I take it way too seriously. And she's a student who's failing my class. So I'm a professor at a prestigious New England university and my girlfriend is a senior in my Intro to Western Civilian.

[Interviewer/Assistant]

I know, why is she a senior in the intro?

[Gary Goleman]

And they couldn't sell it. A production company paid for the special. Nobody wanted it. And I Said, but this was the best I get and I can't even sell it. And it was much easier to sell specials back then. And it just devastated me and was sort of part of a number of different things that happened to me. I lost my dad, and so all these things sort of came together to keep me from getting out of the house and getting out of bed a lot of days. So my manager, Brian said, what if we did a hybrid of a special with a documentary? I just worked with a documentarian. His name is Mike Bonfiglio. And Mike had just worked with Judd Apatow on the Avett Brothers movie and a couple of 30 for 30s. And the Garry Shandling. The Garry Shandling documentary. And he later did the George Carlin.

[Stephen Dubner]

You liked Garry Shandling, I'm guessing.

[Gary Goleman]

Yes.

[Stephen Dubner]

Yeah. Right.

[Gary Goleman]

Yeah. He was one of my heroes. Him and Richard Lewis, I think were the two. And David Brenner also.

[Stephen Dubner]

But only Jewish comics. Right.

[Gary Goleman]

It's okay. It's interesting because I also loved Richard Pryor and George Carlin, but the two that I saw myself in were Gary,

[Stephen Dubner]

Steven Wright you liked a lot as a kid.

[Gary Goleman]

I loved Steven Wright, yeah. Yeah. But I didn't. I didn't think I could pull off that style. It was too smart and too hard. And so did you like Lenny Bruce a lot? No, I didn't. I didn't understand. I didn't understand the context. I think Lenny Bruce is all about the context and how brave he was. There were certain Lenny Bruce jokes that I liked, but for the most part, I just think of him as somebody who other comedians were standing on his shoulders. Pryor and Carlin and Richard Lewis types. Yeah.

[Stephen Dubner]

All right. Sorry I interrupted. So you're.

[Gary Goleman]

This is how a conversation works.

[Stephen Dubner]

This is how a conversation works. Yeah, I agree.

[Gary Goleman]

But I must have at some point read somebody saying that you should write the book you want to read. And I extrapolated that to being the comedian I would want to see. So Emerson in Self Reliance said that the specific is universal, which seems impossible, but I have found that the more specific an art is, the more it resonates with me.

[Stephen Dubner]

What's your mental state before a show? Are you excited? Are you anxious?

[Gary Goleman]

I'm really excited.

[Stephen Dubner]

Excited.

[Gary Goleman]

I'm anxious in the same way that I used to get excited before a basketball practice or a game. I can't wait to go out there and play. Although there were times in basketball where my confidence was so lacking that I was nervous, anxious, afraid. And that's happened in comedy, but that's very rare.

[Stephen Dubner]

Is the anxiety or the loss of confidence in sport, you think greater than or less than performing?

[Gary Goleman]

Almost identical. It's so interesting.

[Stephen Dubner]

It's almost paralyzing.

[Gary Goleman]

Yeah. And in sports, it affects your fine motor skills, so it can really affect your shooting. And in comedy, the audience can sense that the comedian is nervous.

[Stephen Dubner]

And you're a good basketball player, we assume.

[Gary Goleman]

Yes, for somebody who doesn't play basketball.

[Stephen Dubner]

But you were good when you were.

[Gary Goleman]

If you don't play basketball, you'll think it's like magic. Like, a magician can tell whether a magician is good, but a layperson can't tell. So you would say, like, sometimes I'll play with people and I'll make so many shots, they'll be laughing because they think it's absurd. But if I play with a real basketball player, they're like slow and can't jump, and if I get too close to him, he'll miss.

[Stephen Dubner]

So since I don't really. I haven't played basketball since I was probably 16, so.

[Gary Goleman]

Oh, we should definitely play.

[Stephen Dubner]

Yeah, we'll definitely.

[Interviewer/Assistant]

I would love it.

[Gary Goleman]

Okay.

[Stephen Dubner]

Gary says that over time he has developed a strategy for when he loses confidence in himself, whether it's in basketball or in comedy.

[Gary Goleman]

Whenever I'm working on a project, I think of another project where I was ready to throw in the towel and I stuck with it and I was able to finish it. And that goes with this other thing that I've learned, that any project, it's a pretty good sign if at some point you feel over your head because it means you're stretching your comfort zone

[Stephen Dubner]

and you're, what are you doing now? That's stretching for you.

[Gary Goleman]

The one person show was something that I wrote. I probably finished writing a year ago, and now I'm touring it and I did it.

[Stephen Dubner]

This is grandiloquent.

[Gary Goleman]

I did it off Broadway. I did Grand Eloquent off Broadway. I think. 36 shows. And about three weeks into rehearsal, I said to my wife, I've bitten off more than I can chew and this opening night is going to be a disaster. I can't memorize all these things that I wrote. And. But then I thought, oh, well, failing is part of the whole thing. And there's really no artist who's never failed at anything. And I was able to figure it out and memorize it. It requires staying up way past what I am comfortable with.

[Stephen Dubner]

How do you do that? Just yourself or do you have Sade run lines with you Just by myself?

[Gary Goleman]

I use a lot of the Pomodoro

[Stephen Dubner]

method setting the timer for whatever.

[Gary Goleman]

Yeah, and writing it out and a lot of mnemonics so that there was a story, and then there was this weird story in my head that connected all these things. And there's one line where I say my mother would use Yiddish in the house to heckle me. And so it felt like I was being heckled by my ancestors. And then that went into the next joke, which was about babysitting. So I pictured an ancestor, which is this. When I tell you my mother's mother was one of the most unattractive people I've ever seen in my life. She looked like Madam from Solid Gold, like the Wayland Flowers puppet with that long chin and she had a bun on her hair. And so I picture her babysitting with me, which, if you grew up in my house, you knew this woman would never be allowed to babysit. She had babysit my brother Max once when he was 2 or 3, and he had swallowed an entire bowl of grapes hole. And they had to, like, take him. They had to rush him to the er. So she was never allowed to babysit.

[Stephen Dubner]

But it wasn't a grapefruit.

[Gary Goleman]

Yeah, I have this. So I have this image of my grandmother, and that relates to the high cost of babysitting in the 1970s. My mother bringing me everywhere and then that. So, yeah, it was interesting to memorize it so that next time, and there will be a next time when I'm over my head, I will say, yeah, you said the same thing about grandiloquint.

[Stephen Dubner]

You smile so much. Is it strategic?

[Gary Goleman]

Yes, because it's part of certain punchlines and it relieves some tension.

[Stephen Dubner]

They say it's also good for you.

[Gary Goleman]

Yes, but also, I can't tell you, Jeff Garland asked Bruce Springsteen, what does it feel like when, you know, Badlands is next in the concert? How does that feel? And I thought that was such a great question. And with most of my jokes, I feel the way Springsteen must feel when Badlands is next. I'm like, oh, you like that one? What do you hear this one? Because I really worked at this one.

[Stephen Dubner]

That's a great feeling.

[Gary Goleman]

I would imagine it's such a great feeling, but that's where the smile comes from.

[Stephen Dubner]

It's also a great feeling that you get for two seconds. That reflects 30 hours of working on your own earlier. Right?

[Gary Goleman]

30 hours is. No, I mean, the abbreviating the States joke started when I was 6 years old and found a book in which they listed the abbreviated for the States. And because there was no Internet, I just Memorized it because it was something I can.

[Stephen Dubner]

You still do that joke? Do you still do it?

[Gary Goleman]

I don't do it anymore because comedy, fortunately and unfortunately, isn't like music where you want to hear the hits, but. Yeah.

[Stephen Dubner]

How long would it take you to get it back if you had to?

[Gary Goleman]

I could listen to it on a subway ride and be able to remember it.

[Stephen Dubner]

Yeah. Do you feel your memory is freakish?

[Gary Goleman]

Yeah. It's unusual to remember so much from a childhood, because I was reading something today where somebody was saying that they couldn't remember their elementary school teachers. And I'm like, I remember the custodians and the nurse and the teacher's aides.

[Stephen Dubner]

Yeah.

[Gary Goleman]

But because of my depression, I lost a lot of memories.

[Stephen Dubner]

You did?

[Gary Goleman]

Yeah.

[Stephen Dubner]

Do you want to just quickly describe your family that you grew up in?

[Gary Goleman]

I mean, some of the most unimpressive

[Interviewer/Assistant]

people,

[Gary Goleman]

and yet so critical. It astonishes me that people this average could be so critical about every aspect of everyone. Judgmental. My mother. I brought a girlfriend home one time, and within a minute, the woman made the mistake of being far enough away from my mother where she couldn't hear what my mother said. My mother said, oh, so homely.

[Stephen Dubner]

Oh,

[Gary Goleman]

and it just.

[Stephen Dubner]

Was your mother pretty?

[Gary Goleman]

No. There were pictures of every old lady where they were young and their wedding pictures. She was a beautiful bride, but she had no right to be denigrating anybody's appearance. And it's just such a tacky, gross thing to be as somebody who comments about people's physicalities. And anytime somebody came on TV with bad teeth, which is half the people who want to be interviewed for the nightly news, my mother would say, ugh, get your teeth fixed. Or sometimes she would go, ugh.

[Interviewer/Assistant]

Like that.

[Gary Goleman]

When somebody would come on, like she. Like the most critical. And then my brother's big thing was to criticize me. Everything about me under the auspices of, well, we don't want you to get a. A big head. But it was just. It was diminishing and belittling, and it just. It got to the point where. And I could never put it into words until this sentence that came to me one day. And it's so simple. I don't like how I feel about myself when I'm around these people.

[Stephen Dubner]

So did you cut your family off? How'd you deal with it?

[Gary Goleman]

I cut them off from time to time. Or my mother didn't speak to me after the book came out. She didn't speak to me for six months.

[Stephen Dubner]

Yeah, she doesn't come off so, well.

[Gary Goleman]

Well, the thing is, she didn't mind that anything really in the book except that I had told these stories of her stealing Hallmark cards in the 1970s from the greeting card store she worked in. And she was just devastated by that. I didn't do it for any kind of revenge. I just thought it was really funny that we had a lot of things in our house between my mother and her twin brother who was a burglar, that we had.

[Interviewer/Assistant]

We had.

[Gary Goleman]

We were poor people, we were on food stamps and free lunch and welfare and public assistance, and yet one time we had a pinball machine in our house, had a gumball machine from a grocery store in my bedroom, and nothing we had in our house that cost more than $100 had a receip.

[Stephen Dubner]

You're well now.

[Gary Goleman]

Yeah.

[Stephen Dubner]

And that's awesome. And I'm just wondering if when you're working now, if you think about being not well one day and if anything you're doing in your work may kind of lead you to that by the specificity, because you're just bearing. To me, it feels like you're really baring your soul, but because you're funny, it's delicious. It's not painful, but it's very, very specific. So I feel like you've X rayed yourself from every direction and put it out there. And I just wonder how you feel about living with those specificities down the road, perhaps.

[Gary Goleman]

It's an interesting question. One thing, and I think this maybe is just a corollary to this, is that part of the reason I am so vigilant about staying well is that I am concerned that I will let certain people down who. There are so many people who will tell me how the Great Depression resonated, how. I mean, one of the best things that I can hear is that they were able to watch it with a family member and the family member was able to understand better what it's like because that was always the most frustrating part of life in general. But specifically depression was being able to describe what was going on inside you. And the fact that this special was able to allow people to share how they were feeling. That was a great compliment to me. So I feel there is something above just feeling well for myself, tied up in me being vigilant about feeling well, that I don't want people to feel like, oh, what hope was there for me, Gary, was my.

[Stephen Dubner]

I mean, do you feel like you've become a standard bearer not just for comedians talking about their own mental health, but like for all humans? Who?

[Gary Goleman]

No, no, but amongst. But for comedians, I guess I just. It was always a fantasy of mine that my suffering, I would be able to make people feel a little bit better in the way that I had been.

[Stephen Dubner]

But isn't that a little weird to use your suffering to make other people feel better?

[Gary Goleman]

Well, I guess what I'm saying is that. That when, for instance, quarterback Terry Bradshaw and Bruce Springsteen, these men's men came out and said, we are suffering. We've been depressed. Somebody said to Terry Bradshaw, but you're Terry Bradshaw. And I'm sure I probably would have said, but wait, you're Bruce Springsteen. And so I figured out that I was, in a way, a similar voice to certain people, that they would say, well, I thought I would be happy because I was a comedian and I was successful, but it wasn't like that. And I thought, oh, I just haven't gotten successful enough. And then you hear Bruce Springsteen and Michael Phelps, for instance, and you realize, oh, it has nothing to do with achievement. This is chemical. And it lets you off the hook, which I think is such a great. A great service that comedians can provide. But it works the other way too, I always think, because they let you off the hook also for being racist and sexist and homophobic. So you gotta be careful.

[Stephen Dubner]

I think you have some show and Tell. It looks like you brought. What did you bring?

[Gary Goleman]

But before I go to show and Tell, for the people watching who are obsessive compulsive, I wanna fill in the last piece of how the. How the special got made, which was in the meeting where I met Mike Bonifiglio. And he said, do you mind if I ask my friend Judd if he would like to work on this? And it was Judd Apatow, of course. And I said, yes, yes, yes, you may. Right? And then I did an audition where I did the whole show. And a couple days later. But I will say one interesting thing was that I had to be very careful because I knew a rejection could throw me off track. And I remember my wife, in the interim between me auditioning and them saying, yes, my wife said, this is really unfair because I am going to have to live with their decision. But I had said, I will be disappointed. I will keep touring the show, and if it doesn't wind up on hbo, I'm fine with that. And of course, then it happened. I never had to really live with it, but that's how it came to be. And then we shot it in June. It aired in October.

[Stephen Dubner]

Where'd you shoot it?

[Gary Goleman]

Changed everything. In Brooklyn at a place called Roulette. Yeah.

[Stephen Dubner]

And it changed everything. Meaning what?

[Gary Goleman]

Meaning I was able to write a book based on people who watch that. And then I've had great success in touring my act since then. So the three hours that I've written since then, I've been able to tour every year or two.

[Stephen Dubner]

Does any part of you think that, oh, if only I'd been well the whole time that I could have elevated myself or advanced in a even different way?

[Gary Goleman]

Sometimes, but only because I sometimes tell myself, man, it's a good thing you went crazy, because you would have run

[Stephen Dubner]

out of material otherwise. Well, I mean, it's good material. It's really good material.

[Gary Goleman]

And also, just doing really good observational jokes didn't really bring me the following that I have now.

[Stephen Dubner]

So you're saying you became known.

[Gary Goleman]

I became better known.

[Stephen Dubner]

The depressed comic.

[Gary Goleman]

Yeah.

[Stephen Dubner]

But now grown beyond it to some degree. Although many people, I'm sure, still know you for that.

[Gary Goleman]

Yeah, but there were people before that who just knew me as an observational.

[Stephen Dubner]

I knew you as the. The two letter state.

[Interviewer/Assistant]

Yeah, yeah, yeah.

[Gary Goleman]

It was the same abbreviation. Yeah, that was my Born to Run.

[Stephen Dubner]

Yeah, it was your Born to Run. I'm so glad you're back.

[Gary Goleman]

Me too.

[Stephen Dubner]

I'm so glad you're back.

[Interviewer/Assistant]

Me too.

[Stephen Dubner]

This episode of Better in Person is presented by ChatGPT. ChatGPT work moves beyond answers into getting real work done. It's a new experience in ChatGPT for bigger multi step projects across web, mobile and desktop. You can give ChatGPT work goals and have it gather context, choose an approach, create the output and continue iterating all while you stay in control. It can help turn messy inputs into useful outputs like briefs, spreadsheets, dashboards, presentations, prototypes, landing pages and workflows. You can even ask ChatGPT work to take on entire workflows with a single request. Here's an example. It can turn customer research into a campaign brief. Use that brief to create marketing assets and adapt those assets for different markets, carrying context through every step. Put ChatGPT to work on your most ambitious ideas and projects. Download the new ChatGPT desktop app today. On any day that it's above 40 degrees Fahrenheit in New York City, Gary Goleman plays basketball outdoors to help maintain his mental health. One day when it was maybe 43 degrees, I tagged along. He was shooting baskets on a court up in Central Harlem. There was no one else around.

[Interviewer/Assistant]

Nice.

[Stephen Dubner]

All right, I want to ask. Do you mind if I ask you questions? While you shoot?

[Interviewer/Assistant]

No.

[Stephen Dubner]

All right, here's what I want. Before every shot.

[Interviewer/Assistant]

Yeah.

[Stephen Dubner]

I simply want you to tell me one thing that you love about basketball.

[Interviewer/Assistant]

Okay. Larry Bird. The Boston Celtics.

[Stephen Dubner]

Nice. What about for you? What is, what does it do for you?

[Interviewer/Assistant]

Oh, basketball is good for the heart. Basketball is an anti anxiety.

[Gary Goleman]

Gary Goldman.

[Stephen Dubner]

So you were very good at basketball when you were a kid.

[Interviewer/Assistant]

Yeah.

[Stephen Dubner]

But you ended up playing not college basketball, but college football. What happened with you and basketball in there?

[Interviewer/Assistant]

Well, I would say part of it was I didn't believe in myself and I didn't value the enjoyment of it. I wanted to get a scholarship and I didn't value how much fun I had and how much I looked forward to it. And at the time, they were giving literally 10 times the number of football scholarships than basketball scholarships, bigger teams, because they had 100 players at the time. I had the intersection of a bad coach. In my book, I refer to him as Ron Bitter. He was a very short man who didn't teach us anything about basketball. He was just. He took everything he had learned about Bob Knight except these skills and technique. Chair throwing, the cruelty, the chair throwing, the swearing. And I would, I was discouraged. And when some football coaches showed me the type of enthusiasm that I deserved in basketball, I immediately was hooked on that type of feeling. And ultimately they were able to get me a four year scholarship to college. So it worked out in some ways. But I think I would have been happier had I reached my potential in basketball. But I will tell you that when I. What I've decided to do is apply that type of love to my comedy and my writing. And that's been very satisfying.

[Stephen Dubner]

I'm happy for you that basketball is, again, a fun part of your life. But I also think it's a good lesson for anybody watching. Like the thing that you love, you gotta remember to keep the love in it or it turns into a different thing.

[Interviewer/Assistant]

No, I know, I know.

[Gary Goleman]

It's just.

[Interviewer/Assistant]

And I, I feel so grateful that I was able to rediscover it, actually, after I started to feel better from my depression.

[Stephen Dubner]

Was it a big part of your getting better?

[Interviewer/Assistant]

Yes, absolutely. Because I always used to take for granted that there were so many aspects of basketball that were antidepressants. I think the thing that people get put off by is when they're not immediately good at it or if they're not as good as they used to

[Gary Goleman]

be when they were younger.

[Interviewer/Assistant]

That was part of it. I had to come to terms with the fact that I would never dunk Again. And that I would be shown up by much younger people frequently. But if you can. But that's also a great lesson, which is to curb your ego.

[Stephen Dubner]

I've been asking my guests on Better In Person to bring some show and tell. The architect Bjarke Ingels brought some synthetic moondust. As you'll hear later in the season, the rocker and writer Warren Zanes brought in a piece of Beatles memorabilia with a heartbreaking story attached to it. So what did Gary Gallman bring? A big notebook with stickers on the COVID and every page absolutely crammed with joke ideas and much more.

[Gary Goleman]

All right, so this is my most recent notebook. And the first thing is I make a collage.

[Stephen Dubner]

Yes, you do.

[Gary Goleman]

Of stickers and photographs. This is my favorite actor, comedian Chris Elliott.

[Stephen Dubner]

Oh, yeah.

[Gary Goleman]

The back is a lot of set lists and transcription.

[Stephen Dubner]

Can I see a set list?

[Gary Goleman]

Yeah. So here's a set list. Yeah, Just walk us through that. August 27th gen X wave traffic. The Gen X is the last generation that will wave to you for letting them into traffic. Microwave popcorn button was a diversion from the microwave company's inability to get it to make toast.

[Interviewer/Assistant]

And the same thing happened to aliens

[Gary Goleman]

where they were able to make the ufo, but they couldn't figure out how to manage the last 10ft, so they put out a ramp. And that's. And so that's the interesting thing that I love about comedy, is a lot of it is just trying to make connections between things that aren't connected. And so that's fun. Now that you've said it.

[Stephen Dubner]

The toast failing seems large to me now.

[Gary Goleman]

Shouldn't it have been like, yeah, of course it can make toast and it cannot. It can make a turkey in 11 minutes and it can't make toast. But then it also has a diversion. Not a diversion, a digression. Where the toast people are frantic over the microwave oven's prospects for toast making and pushing them out of business. But then the man who runs the toast. And the problem with this joke is it feels too much like the abbreviating the States. But the man who runs the toast consortium says will always have bathtub suicides. Like, that's. And to me, that's the

[Interviewer/Assistant]

bottom.

[Gary Goleman]

That's the bottom line of capitalism. That's the way they think. I don't know.

[Stephen Dubner]

We'll always have bathtub suicides.

[Gary Goleman]

Yeah.

[Stephen Dubner]

Do you remember writing that line?

[Gary Goleman]

I remember thinking of it on stage.

[Stephen Dubner]

Oh, yeah.

[Gary Goleman]

Yeah. So then I wrote it down afterwards because it got tough.

[Stephen Dubner]

Did it work the first time?

[Gary Goleman]

It got such a reaction. It got such a reaction. Like it was similar to what happened here where people are like, ah. Cause it's really especially for a depressive to talk about, to talk about bathtub suicide.

[Stephen Dubner]

Also, I could imagine you trying to have toast in the bath somehow, right?

[Gary Goleman]

But then I also followed up with cause this is where the real writing comes in. So you have that line where he says, we'll always have bathtub suicides. But then I thought of something that he says after that, you want to frighten me? Tell me they've outlawed dead end jobs and loveless marriages. Then I'll start panicking because as long as there's despair, we will sell toasters. The man was a psychopath.

[Stephen Dubner]

Really. I'm so glad you came by. It's great to see you and I'm so glad that you're doing well, see

[Gary Goleman]

each other and spend this time together.

[Stephen Dubner]

Thank you. And I think that you're. I really think you're an inspiration to a lot of people. So. Well, well done, man.

[Gary Goleman]

Oh, that's so nice to hear. Thank you.

[Stephen Dubner]

All right. Thank you, Gary Goleman.

I hope you enjoyed this audio edition of Better in Person with Gary Goleman. But remember, this is a video show and you can watch this episode on the Freakonomics YouTube YouTube channel or on Apple Podcasts. Let us know what you think. Our email is better in personreconomics.com or you can also write to [e-mail] we will be back soon right here with more Freakonomics Radio. Until then, take care of yourself. And if you can, someone else too.

[Gary Goleman]

Beautiful. It's so decadent to have somebody have somebody lint roll you.

[Interviewer/Assistant]

Oh, my gosh, what a life.

[Stephen Dubner]

Thanks again to ChatGPT for sponsoring today's episode of Better in Person. ChatGPT can help teams move from goals to real outcomes. Put ChatGPT to work on your most ambitious ideas and projects. Download the new ChatGPT desktop app today.