Josh Gondelman: I Kind of Got Bullied Into My Career
In Conversation with Will Schwalbe on But That's Another Story
But That’s Another Story is the new podcast about how books change our lives, hosted by Will Schwalbe, bestselling author of The End of Your Life Book Club and Books for Living. In this episode, Will talks to comedian Josh Gondelman about David Foster Wallace’s Infinite Jest, his comedy career, and the value of goodness over niceness.
Will Schwalbe: Hi, I’m Will Schwalbe, and this is But That’s Another Story. I’ve been thinking a lot about biceps recently, in part because spring is finally here. It was a long winter with three—yep, three—Nor’easters on the east coast. We just had our first nice day and many of my fellow New Yorkers are already out on the street showing off their buff biceps. I guess I know where they spent the winter—hitting the gym, lifting weights. That’s the thing about biceps. You need to work hard to get and keep them. I may have some work to do there.
I’ve also been thinking a lot about empathy. Now, I can’t prove this, but I’m pretty sure that the most empathetic people in my life are all readers. When you read, you’re really listening to another person. You can’t interrupt. You can’t change the words on the page. And listening to someone else, page after page, chapter after chapter, is like walking many miles in their shoes. Reading helps you exercise your capacity for empathy. And the harder you work at it, the stronger it grows. I like to think about it this way: libraries are really gyms for the soul, and books are the free weights that help you build empathy instead of muscles. So from now on, when I say I’m going to the gym, I’m going to leave it a bit ambiguous. Maybe I’m going to pump some iron. Maybe I’m going to crack some books. No matter which, I’ll come out stronger. And recently, I got to talking about the empathy muscles you can build through reading with today’s guest.
Josh Gondelman: Hi, I’m Josh Gondelman. I’m a writer, stand-up comedian, and a comedy writer for Last Week Tonight with John Oliver.
WS: It’s pretty likely that Josh Gondelman has made you laugh before. Whether making jokes on Twitter or for the New Yorker, he does the kind of comedy that makes you laugh but also makes you think, wow, what a nice nerd. That’s a characterization that has hung around since he was a kid growing up just outside of Boston.
JG: I had a Screech from Saved by the Bell kind of vibe in that I hung out with people and had friends while having like big, curly hair and being generally a dork. I think it was a friend’s mom started calling me that, and then it just stuck. Like, when grown ups are giving you your mean nicknames, that’s like, a rough moment as a kid when you’re being bullied by adults.
I played sports because I think it’s mandatory in the greater Boston area regardless of your aptitude. It’s like, well, what else would you be doing?
When I was young, like young young, I would read all the time. I would read when I was walking places. My taste was like, all over the place. I wouldn’t even call it taste. It was just like, what was there. My mom has a ton of books, and so I started reading like, Lord of the Flies and Catcher in the Rye really young, and then for some reason I got into Stephen King, even though I was terrified of all his books and I didn’t like that feeling, but I liked the stories.
WS: That enthusiasm for stories only grew as Josh got older. In high school, he performed in school plays and even wrote a play that he submitted to the state drama festival. And his more theatrical inclinations would come in handy in one of his first jobs after college.
JG: So, when I was 24, it was 2009 and I was a professional preschool teacher. I worked with three and a half to five year olds, we’re the pre-K II class, so right before the kids would leave for kindergarten.
We would do a holiday play every year and a little graduation ceremony that I think we kind of scaled up when I got there, because I was like, oh, this is something I could bring to the table. Because I wasn’t—I’m not crafty, and so there’s a lot of preschool that’s like, let’s turn this egg carton into a caterpillar! And I just didn’t… I wasn’t good at that, like innovating those kind of things and so I would do kind of like drama stuff and it was a lot of fun. I really enjoyed it.
WS: And Josh was also enjoying exploring something else that he was good at: comedy.
JG: My friend Joe Smith, which sounds like an alias but is his actual name, had started doing stand up and mutual friends had been like, you should also do it! Like, Joe’s doing it, why aren’t you doing it? You want to do it. I uh, I got bullied into my career.
So when I was teaching, this would be kind of like a typical day. I would get up, often exhausted from being out late doing stand up the night before. So I would, on my worst days, when I was like, I can’t believe I’m driving myself in, I would put on a shirt and tie and then everyone would go, wow, you look great today! And I’d be like, I don’t! But uh, tricked ya! Then a couple days a week, I would bounce out of there and drive to the suburbs and tutor high school entrance exams, SATs for a couple hours in the afternoon, and then do shows most nights.
It was just a lot, burning the candle at both ends and then creating a third wick in the middle. I really enjoyed teaching. I enjoyed the day to day but I was kind of like, I was starting to get this feeling. It was coming on where I was like, I think I can do more with this other stuff, with the comedy stuff and the writing ambition that I had. And I was like starting to get a little itchy to see—to kind of take a shot at that.
WS: Was there a day that you woke up and said, I’ve got to give this thing a try?
JG: I think it was just kind of was blossoming little by little and I had friends that were kind of succeeding more. I had friends that had moved to New York, friends that had moved to LA, and 2009 was kind of like the exact middle between professional and recreational.
WS: Josh decided to take a road trip across the country with a comedian friend. A sort of research and development mission for his comedy career.
JG: I wasn’t like, making a lot of money on this trip. I think the one weekend that I got paid for, um, I lost the check and then by the time I went to deposit it, it was like, no longer valid. It was mostly an investigation.
WS: To save up money for the trip, he moved back in with his parents briefly and found himself with a bit more time on his hands than usual.
JG: On thing I really like but I never make the time to read is like, just giant books.
WS: And there was one book that had been recommended to him over and over again: David Foster Wallace’s Infinite Jest.
JG: I saw it in a bookstore, there was like a big paperback edition with a foreword by David Eggers, whose work I liked, so that kind of hooked me in. And the foreword, I was very intrigued by it.
David Eggers wrote, I’m a writer, so normally when I read a book, even if it’s something that I would never have thought to write or didn’t have technical ability to write, I would view it like a mechanic looking at a car. Like you have the general ability to understand what makes it work and open it up and put it back together. When I read this book for the first time, it was like peering under the hood of a spaceship. It was like, I don’t what makes this go, but it’s like a wondrous thing.
WS: When we come back from the break, Josh goes for a ride in that spaceship.
WS: Josh Gondelman was 24 years old and embarking on a career in comedy when he picked up David Foster Wallace’s Infinite Jest. And though the book had a significant impact on him, he has no illusions about the novel’s reputation.
WS: When we asked you to choose a book to talk about, a book that changed you, or moved you or affected your life, you were a little hesitant to choose Infinite Jest.
JG: Yeah, well, it feels like such a cliche. Just like, such a bald white guy with glasses… like of course I like that and of course I’ve seen They Might Be Giants live in concert several times and of course my Jewish friends and I were very into the Wu Tang Clan in our early teens… It just feels like one of those things that’s like, oh, yeah, obviously.
WS: The novel is a sprawling, story set just outside of Boston, near where Josh used to live. There are many intersecting plots—there’s a tennis academy, there’s a residential drug and alcohol treatment facility, there’s some radical Canadian politics—but it’s perhaps best known for its elaborate endnotes. But Josh says those aren’t what he remembers most about Infinite Jest.
JG: I think a lot of the things that people like about David Foster Wallace’s writing are not necessarily my favorite parts. I think people get really into how much a virtuoso he is, which I think is true, and I think it’s like really dazzling, but the way that people get wrapped up in that is maybe what gives it the kind of ugh, of course he’d say that. But there’s like so much heart and heartbreak in Infinite Jest that people don’t talk about as much, and it really like, moved me.
JG: I really think it made me, by ten percent, a better human person. I just think that the way addiction and depression were described in that book… it was just a way that reached me really specifically and was a kind of descriptive experience that I hadn’t had as much exposure to.
WS: Growing up in the late 90s and early aughts, Josh says he received the typical Just Say No spiel in health class.
JG: It was kind of practical. There was a lot of, don’t do drugs, which is fine. And there was still like, this is what drug addiction looks like, and it ruins your life and you do things you wouldn’t otherwise do, and it destroys your body. I remember seeing, you know, you’d get pictures of brain scans, and you’d be like, after you’ve done ecstasy once, your brain has giant holes in it. And you go, oh, that’s scary.
I had friends that were drinking underage, and I was just like, oh, no, I’ve been told that’s bad. Like I didn’t really drink until my mid-twenties. Partly because I drove everywhere for stand up, but partly because I was just like, well, I don’t need to get mixed up with this!
WS: And though those fear-based health classes may have worked on him, Josh says the education was incomplete.
JG: I was very fortunate not to have worse information from my health classes. I think so many people grow up just getting the worst urban legend, whatever you want to call it experiences and descriptions of that where you get no kind of compassion from it. You know, you don’t want anything bad to happen to people, but you get that sense of, oh, that guy’s kind of a fuck up, and that’s something that happens sometimes. And it’s unfortunate when it happens, but you don’t get the sense of what a tragedy that is on an individual basis.
WS: But reading Infinite Jest changed that for Josh.
JG: I definitely knew people who were struggling with drug addiction and drug use… but it just was the kind of thing where you’d go, oh, it’s such a shame that that happened. Right, like, oh, I feel bad that their life is in a bad place because of this, and hopefully they can get it right. And that’s like… a totally fine, to me, a totally fine start. Right? That’s not the be all end all though, though. It’s like, oh, shoot, what they’re up against is not a series of bad choices necessarily, it’s a pathology that’s biological and psychological, and it must really hurt to feel like you’re fighting and failing all the time. Or to not even see that that’s a possibility, to fight against this.
Infinite Jest was, I think, the first time that I really was immersed in a work of art that made me go, oh, in addition to the physical degradation and the danger of depression, there’s also a lot of pain… so that, it kind of expanded my understanding of that whole arena. There’s just a compassion that it engendered in me—not like I was a callous person before, but I knew so much more. It was the emotional side of that education.
WS: And that education has also had an effect on Josh’s career.
JG: I definitely think that the book informs the work that I do, the comedy and writing that I do.
I’m often described as a nice person, and actually, I think nice is fine. I value niceness. But now, as a grown person, I value goodness above that. Because niceness doesn’t change anything and goodness changes things. But it’s not like I’m like, well, I can be kind of dickhead as long as I’m giving to charity and going to marches. You know, that’s not something I believe about myself, certainly. But I think this book, Infinite Jest, blew the lid off what I saw as my potential for myself, even. Because I think my jokes were nice and I was—they were probably cleaner, back then, when I started, I probably cursed less and talked about sex less or, you know, adult themes. But I think that… reading Infinite Jest was part of the progression from going from clean, to, like, more sincere and more open-hearted comedy.
I think it just made my work a lot richer too, to hold that as a value instead of, like, oh, “nice clean jokes about nice fun things.” But to me, to instead be like, oh, “jokes that try to demonstrate goodness more,” and—even if that ta—there’s a little more edge to it or a little more grit to what I’m talking about. Um, because just being nice and polite you sometimes avoid getting into the guts of what’s real, and I think there’s a value to all different kinds of things, but, like, it showed me that more was possible.
If it seems daunting and the reputation is that it’s opaque and there’s no point of entry—I think it’s a very pleasurable reading experience and a very worthwhile reading experience. In a heart way and not just a masturbatory intellectual like, I read the longest book with the least satisfying storylines. You know, I don’t have a lot of stake in that, I like when things kind of… I want everything—I told my wife this recently, I was like, I just want everything to be “Born to Run.” Like, I just want everything to be like big and full of feelings and it gets stuck in your head and fun. And this book pushed all my buttons in a way that people don’t give it credit for being those things.
WS: So this is the Bruce Springsteen “Born to Run” of novels.
JG: Yeah, it’s big and everything’s in it and—saxophone—yeah, like, and the bells, you’re, like, “Who does bells?”
WS: But That’s Another Story is a production of Macmillan Podcasts. Thanks to Josh Gondelman. You can find him on Twitter @JoshGondelman and hear his jokes every Sunday on Last Week Tonight with John Oliver. If you’re enjoying our work, please be sure to rate and review the show on iTunes — it really helps others discover the program. And be sure to subscribe on Apple Podcasts, Stitcher, or wherever you listen. If there’s a book that changed your life, we want to hear about it. Send us an email at AnotherStory@macmillan.com. We’ll be back with our next episode in two weeks. I’m Will Schwalbe, thanks so much for listening.