The Rumpus Interview with Dan Kennedy

While many readers are familiar with the melancholy persona he’s adopted—and despite having written a new novel about a life falling apart—author Dan Kennedy is finally ready to admit something to the lit crowd, here and now: he loves mainstream American comedy, films like Ghostbusters and Wedding Crashers. Not only that, he has plans to write those types of movies. There’s one underway, in fact. And as Kennedy points out, he essentially grew up in a mall and he isn’t going to hide it from us, anymore, the way he hid Purple Rain behind his Nick Cave records. He can run lines for Fletch on the spot. He can dissect the central premise of Meet the Parents and suddenly you realize that it’s not just broad comedy, that themes of love and loneliness and aging and fear of the unknown run through it.

This passion for the genre of comedy that defined his formative years goes beyond the work he’s widely known for, which includes his prolific, oftentimes dark writing for McSweeney’s Internet Tendency and the stories he tells onstage at The Moth. In the thirteen years since he started seriously writing humor, Kennedy hasn’t really explored work with happy endings. His most frequent target is himself and the stories are somewhat bleak. Granted, in that same timeframe, he has written three books, numerous magazine articles, and a seemingly endless array of memorable humor pieces, all while hosting a popular weekly podcast and live storytelling events. His novel will be released in May. For many, that would be enough. But Kennedy has a defined goal (which is at odds with his nature): just keep moving forward.

I first became aware of Kennedy’s work in the early 2000s, while he was busy making a name for himself on the McSweeney’s website, banging out piece after hilarious piece. He easily ranked among the funniest writers out there, whether he was offering up his failed attempts at flirting, some new Jelly Belly recipes, intentionally bad stand-up comedy, or an advice column that promised to solve your “problems with paper” (generally by deviating into every other possible subject). And, while it’s tricky to choose a wholly representative piece, I would personally suggest that you read “Silly Things My 3-Year-Old Said That I’m Certain the Rest of the World Would Find Sweet and Cute,” right here, before we go any further…just so you know the mind we’re dealing with.

Around the same time that Kennedy discovered McSweeney’s, he was handed a postcard advertising The Moth, the true-life, no-notes storytelling series that originated in New York and is now staged around the world. Kennedy attended an early Moth performance and something clicked for him, he says. After cold-calling the organization’s offices, he began performing at Moth events in 2000. Fast-forward thirteen years and Kennedy is now the host of The Moth Podcast. He also emcees many of the live Moth StorySLAM events in New York and routinely travels with the show. The night before this interview, he’d been in Detroit, storytelling in front of two-thousand people.

As mentioned, Kennedy’s writing has also smoothly made the transition into book form. In 2003, he opened with the very funny Loser Goes First: My Thirty-Something Years of Dumb Luck and Minor Humiliation, a collection of essays detailing his “painfully awkward youth and painfully awkward adulthood.” A couple years later, Kennedy wrote Rock On: An Office Power Ballad, hilariously skewering his year-and-a-half at Atlantic Records, at just about the same time that the music industry was collapsing under its own hubris and inability to cope with the times. And Kennedy’s latest project is the aforementioned novel, American Spirit, described like this:

When Matthew, a forty-something media executive, finds his job, health, and marriage crumbling, he goes native: Lives in his car. Dips his toe in drug-running. Contemplates song lyrics. Takes a really good pottery class. Before long he’s on a stumbling, agonizingly funny vision quest that takes him from a strip-mall parking lot to Yellowstone National Park to a Bali medical clinic, from an unlikely romance with a Hollywood agent specializing in hot young vampire roles to extreme RVing with a disgraced Wall Street trader.

Kennedy admits that a handful of his real-life exploits ended up in the novel. More on that in a second.

I first met Kennedy when I worked at 826 Valencia, a nonprofit writing and educational center in San Francisco. He was on a panel I was hosting, where he helped teach fifty adults how to write humor. I remember him being incredibly funny about being funny—not an easy task. Relatedly, his expertise was featured in the 826 National guide to memoir-writing, The Autobiographer’s Handbook.

Kennedy continues to write for McSweeney’s and GQ Magazine, among other outlets, and, as reported, is now immersing himself in screenwriting, both for television and movies. For this interview, we talked by phone for about two-and-a-half hours. While he was on very little sleep, having just come off the road, Kennedy was lively and engaged. We laughed a lot, while covering a good amount of territory.

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The Rumpus: Let’s talk about your new novel, American Spirit. What was it like to jump into a novel after all these years of writing nonfiction and essays and short humor?

Dan Kennedy: Pretty scary. I started this book before I started Rock On, and I just wrote twenty pages of it and was like, Oh, man, I’m in over my head. I can’t write this character. There’s no way I can write this character. Huh. All right. Better figure out something to do to eat. And so I put that in the drawer and wrote Rock On instead, because it was way more within my range at the time. I think it was 2006. Weirdly enough—five or six years later—pretty much all of the stuff that I was in over my head with, with that character, happened to me. And I was like, Oh. Okay. Wow.

Rumpus: So you had an idea for a guy whose world had collapsed and he needed to rebuild his life, and then you went through your own crises?

Kennedy: Yeah, put it this way: there was a chapter where this character [Matthew] is reading his own X-rays against the light in his kitchen and determines, even though he’s not a doctor, that he’s going to be dying in four months. And two scenes later, he’s waking up in an airport lounge in Taipei, trying to figure out what happened. And that all just seemed stupid and over-the-top. But then I was losing a lot of weight and reading my own X-rays by the kitchen light, going, “Oh my God, do you see that right there? That’s not normal. Look, it’s not on the other side.” And then waking up in an airport lounge in Taipei. The logical argument is just, well, you probably made a certain amount of stuff happen, didn’t you?

Rumpus: Is that what you think? That you made it happen? Did you figure out what that weight loss was coming from?

Kennedy: I had been eating less. It just kind of came down to, Well, you’re eating a lot less. I traveled a whole bunch in that particular year and usually, when I travel a lot, I just forget to eat a lot while I’m traveling, so…

Rumpus: Right. I think we’re the same, in some senses, jumping to the worst possible conclusion. Not too long ago, I had a day where my fingers were tingling and I Googled “tingly fingers,” and it indicated that I’d probably had a minor stroke. So I convinced myself that it was true.

Kennedy: Yeah, Google is the biggest symptom. It’s amazing what happens when you get on there. Just before I left town the other day, I was cold and literally Googled “constantly cold.” And I was trying to find what terrible thing was going wrong with me. And it was like, I just need to put on a fucking jacket. Really, my girlfriend was like, All you’ve been wearing is that T-shirt. No hat or anything. And I’m like, Oh. Okay. Let me get off Google here and go get my jacket.

Rumpus: Right. So when you’re reading your X-rays in the kitchen and trying to diagnose yourself, was she trying to talk some sense into you? Or were you pretty convinced that it was something bad?

Kennedy: Just go read this so-called novel. Oh man.

Rumpus: So a lot of your freakouts actually made it in there?

Kennedy: There was a slightly larger-scale version of what we’re talking about, where you’re convinced that something’s gone so terribly wrong and your doctor’s basically just like, “You’ve been eating not nearly enough food for about three months straight. And it looks like you might possibly have a kidney stone, as well. So that’s the dull pain and the weight loss. You really have to eat more than one meal a day when you’re traveling.” And I was like, “Oh. Can I just show you this one thing I saw on the films?” I actually referred to them as the “films,” instead of my X-rays. You know—technician by proxy.

Rumpus: He’s thinking, “Oh, the films. This guy definitely knows our jargon. I’d better take a closer look.”

Kennedy: Yeah, exactly. He’s like, “You know what? I wasn’t going to take him seriously, but I don’t know—apparently, he went to eight years of school, too.”

Rumpus: Right. “It seems like he’s been doing some research under a kitchen light.”

Kennedy: Yeah. And then, waking up in Taipei was just…I guess I won’t talk about what’s real, what’s not real, what was sublimated, how it was sublimated. But yeah, there was basically this assignment I took and I had to leave pretty late at night and make a weird connection up in Alaska to another plane. And then go down to the other side of the equator. And part of that was this three-hour layover in Taipei, where I just totally conked out in the airport lounge and just woke up, and I was like, “Holy shit, I’m in a Tarantino film. What happened? Am I doing drugs again?” Then it was like, “Oh right, the thing. I said yes to the thing I’m going to write about.”

Rumpus: Do you find that it’s interesting to write about somebody in the middle of a crisis? And that maybe you needed to create these things in your own life in order to know what it’s like to go through it? Obviously with the job at Atlantic Records [which Kennedy detailed in Rock On], the crisis was beyond your control. But in scenarios like waking up in Taipei and not knowing where you are, or by diagnosing yourself in your kitchen, you’re sort of manifesting problems that don’t actually exist.

Kennedy: Yeah, maybe. For a while there, I was taking writing assignments that were totally creating that sense of desperation and urgency, because I have a pretty comfortable middle-class life now. So there was definitely the types of writing assignments where it would be like, “Okay, a messenger is going to come to the door at 11:30 tonight. You’ll have a hard copy of the boarding pass. I’d like you to take that right away and go to JFK and then you’ll be in San Pedro Sula by 6 a.m., and then get down to Roatan by 10 a.m., and then by the time you finally pass out from the all-nighter, you’ll be waking up in the back of a gypsy cab at a roadblock with machine guns. Because these guys in camouflage with machine guns are convinced that there could be cocaine in this cab and maybe you have it.” It was a really weird period.

Rumpus: So the opening of the new novel is that a guy is fired from his job and he starts living in his car in an upper-class neighborhood. It seems like the theme of rebuilding your life continually pops up in your work. There’s also that theme of time passing, being ten years older and not having much to show for it.

Kennedy: How can you not be a little bit freaked out by years slipping by? When you’re little, summer is a lifetime. You get older and the scale of things changes. A year goes about as fast as summer break now. It just takes so long to put anything together.

I had a conversation with a handful of people recently, where you really look at life and what you’ve gotten done to a certain point. There’s a huge thing in America where, basically, your forties start at twenty-five. And people want to be famous by the time they’re thirty, and accomplished by the time they’re thirty-one. We all have these weird timelines, or drives, or whatever. If you really break down an average life, the first eighteen years are almost a write-off in terms of getting anything done, because you’re learning everything from how to walk, to what word to say for something to eat. You know? And so much of that time is a sort of a write-off. And then adolescence is just crazy time. At least from my adolescence, I would’ve been higher functioning if I was just on LSD every day. Hormones and indecision and uncertainty were harder to navigate than psychotropic drugs.

So you kind of have to write that stuff off. You can’t really find your work and find your stride and find your pace during those years, because you’re doing all this other stuff, and everything feels like the end of the world, and the future is totally uncertain, and you have no reference points. You start looking at how much time you’re wasting. Like, when does the show really start? The doors open around twenty-seven, twenty-eight, and the show really starts around thirty-four. You know? When you start looking at life that way, you’re like, Okay, and how long are we here? I have a couple of projects I’m really excited about, but they’re kind of hanging in the balance. Those kinds of things you tell your best friends about and maybe you’ll make ’em happy twice: once when you give them the news, and once when you give them the news that it fell through. And I’m sitting there thinking, Oh, I hope that thing comes through, the thing that we’ve been talking about. That would be really exciting and cool. And then my next thought is basically, While we’re all figuring it out, another year is going to go by.

Rumpus: Right.

Kennedy: It’s just a different economy when all of a sudden, it’s not like, I’m just going to go to the lake and swim out to somebody’s houseboat and drink beer on top of it. It’ll figure itself out over the course of summer. Some nights, it’s like, Let’s all just take our time and see if we’re comfortable with the project. Because god knows, time’s not racing by or anything!

Rumpus: So you feel like a lot of time has already been wasted and things are suddenly more urgent.

Kennedy: Yeah. Kind of. I’m glad we kind of figured out a little bit about getting the hang of this stuff. How much of this can we make happen in six years? That’s really what we’re looking at.

Rumpus: And does this all tie into that story you told onstage at The Moth about your therapist dying, about getting the advice to always move forward, to always choose activities and say yes? Were you consciously trying to throw yourself into purely going for a while, just to see where it would lead?

Kennedy: Yeah, I think I probably was. Because what terrifies me—and this is something I was discussing with [Kennedy’s former therapist] Milton during the period before he died—is my capacity to not take a step forward. Apparently, I just have some kind of low-grade mental disability of some sort. Just some garden variety, unflattering diagnosis, like not eating enough. I’m sure it’s like, Oh, you’re just not that smart. You don’t have to leave the apartment if you don’t have to that day. But it is rather unsettling that I will walk outside one day and be like, “Oh, weird. I guess I haven’t been outside since Monday. Fuck, that’s not super good, is it? Is that normal?” My sister has the same thing. We’d talk on the phone and she’d be like, “Oh my gosh. Apparently I just have no problem living amongst my litter of candy and fast food and watching really bad movies for ninety days.”

Rumpus: That’s so interesting, because it just seems like there’s a real dichotomy in you—you can do that thing where you stay inside for long periods of time, but then you’re also hyperaware of time passing.

Kennedy: Oh, yeah, yeah, yeah! No, completely. Bizarrely. And I don’t know why. God, man, if I would’ve had me as a kid, if I was born even ten years later, I just would’ve been diagnosed out of whatever career I’ve made for myself. I would’ve been medicated right out of it. But I did have that time-passing-by thing from an early stage. I used to go catch tadpoles at a public park pond in Southern California, and put them in a little fishbowl and put them in my room, and I would just watch them turn into frogs and get sad.

Rumpus: Oh, man.

Kennedy: Yeah. If you walk into your kid’s bedroom—which, by the way, he hangs out in eighty percent of his time, staring out the window—you walk into the bedroom and he’s looking into a glass bowl, for hours on end, and you ask him what’s going on, and he looks at you and says he’s just kind of depressed because the legs are starting to come in now and it won’t be long. But god bless ’em, they were just kind of like, “Eh, it’s all good. He’ll be fine.” They gave me, like, a Smothers Brothers record and some books to read.

Rumpus: So your early influences were tadpoles turning into frogs and the Smothers Brothers, basically?

Kennedy: Basically. And just wanting to talk to my dad about death, nonstop. And then listening to [Bill] Cosby or [George] Carlin.

Rumpus: Speaking of your dad—I forget where I read this, but was there a time that you found out your dad’s real name in the middle of a phone call from a stranger?

Kennedy: Yeah! Oh my god. I thought that was a family secret. That was a weird fucking day, too. It was late to find out my dad’s name. This guy called the house, and he was an insurance guy, and he was like, “Is Bill there?” And I was like, “Who?” And my dad’s name is Russ Kennedy. And he was like, “Is Bill there?” I’m like, “Well, no, there’s no Bill in our family. What’s the last name?” And he’s like, “Kennedy.” And I’m like, “Bill Kennedy, huh? Nope. You have the last name right, but there’s nobody in our family named Bill.” And then I hung up.

And then he dialed the number again in two seconds and I picked it up and he was like, “I’m calling for Bill Kennedy.” And I’m like, “Yeah, it’s Dan Kennedy again, we don’t have a Bill.” And he was like, “Are you sure, I just met with him the other day. His street address is blah blah blah.” So I say, “You’ve got our phone number. That’s our last name. That’s our address. But there’s no Bill here.” And the guy was just silent. I don’t know if he thought he was on the verge of belying some huge family secret.

And then my parents were like, “Who was calling?” And I said, “Somebody looking for Bill Kennedy. I just told him we don’t know a Bill.” And my dad was looking at me and he said, “Well, if my name is William Russell Kennedy, would somebody maybe call me ‘Bill’ if they weren’t familiar with me?” And I was like, “Ohhhhhh! Seriously? Oh, right, right, right! Oh, weird! Okay, well…your insurance guy called and you need to get back to him.” And it was this major thing of not really quite looking at my dad in the same way after that. It was like, Bill, huh? Do you tell people you’re called Bill? Do you introduce yourself as Bill to some people?

Rumpus: Yeah, are you just Russ in the kitchen with me?

Kennedy: Yeah! Exactly. Who’s Russ? And who’s Bill? How many lives are you leading? Thank god I’ve been able to put something together because I was just on the fast-track for managing a drugstore in rural California.

Rumpus: So you feel like if you were brought up in the age of more rampant medications, they could’ve really diluted some of this stuff you were able to mine from your life and turn into humor?

Kennedy: There’s like seriously no question. My friends who are parents will talk about testing and syndromes and daydreaming and how they’re worried. I don’t even know what they would’ve done with me in today’s youth culture. Put me in a straightjacket, the hospital, I don’t know what. I definitely would’ve been medicated out of whatever it is I put together for myself.

Rumpus: I’ve noticed over the years that you have a ton of honesty in your writing, but that you oftentimes write pretending to be something you’re not.

Kennedy: Yeah, I’ve definitely got that. What’s the old line? “The biggest lie I tell is that everything’s just fine”? I think I got that. I grew up lower-middle-class and that was a big thing in the suburbs for middle-class and lower-middle-class. It’s like, “Everything’s fine. No need to look twice. We’re normal and everything is great. We are happy.” And I think I might have a bit of that—not knowing how to react honestly in certain situations. If I see somebody in the hallway, I generally don’t go, “Hey, how are you? How’s it going? You know what I like? Weather!” However people do that. I tend to think, Well, what would a person say? It just feels like a part you never quite got the script for. What do people say in the hallway? Do they just keep walking? Is it just people talking? Why don’t I say, “Hey!” No, don’t say, “Hey.” That’s weird. You never say, “Hey.” My first instinct is always try to fit in or something, but that’s starting to change. I’m starting to just not give a fuck, for lack of saying it in a more positive way. But I think you get a little bit older and you’re just kind of like, Oh, I get it. It’s a totally solo show? And we’re all going out at this point? Sweet. No, I really don’t want to go to fucking Thanksgiving with you. But I like you.

Rumpus: Right. So do you feel like, in writing, that’s where you get to be honest in a more blunt, straightforward way? I read something where you said that indulging in the “dark truth” is always funnier. Is it just easier to tell the truth while you’re writing, rather than walking down the hallway?

Kennedy: Yeah. But I’m not really convinced anyone reads it. I mean, even these books, I know people buy them. But do they really read every word? I think about that old saying: “The best place to hide a secret is in the middle of a book.” I think you could probably put your deepest, darkest, most honest thing in there and folks would still come up to you and go, “That was pretty funny! I like the part where you stumble in the hallway.”

In my first book, there’s a suicide letter, written out of spam e-mail headlines. I remember thinking, “What if I killed myself and what if the letter I left behind just copied and pasted all these weird-ass spam headlines—this weird poetry about why it’s impossible to go on. And just leave that behind.” Not that I’m suicidal, or that I’ve ever really seriously considered that. It’s really easy for me to hide behind a really downer, dour thing, but I’m the biggest, excited geek about being alive. My girlfriend is like, “Reel it in.” But I remember that being in there and I sort of thought, I don’t know, maybe that’s kinda screwed, because a lot of young people read this stuff and maybe that’s not so funny, or cool, or whatever. But then no one ever brought it up. You know? Every single person you talk to and every single interview you do is like, “Oh, that was funny. Hey, man, I can’t believe you fell off the window at your house. That was hilarious.” Which is cool. It’s fun. But you read a review that’s like, “It’s funny, but it’s too bad the guy can’t approach anything heavier than humor.” And you’re like, Definitely go to page 178. Because there’s a suicide letter.

Rumpus: Do reviewers actually miss that undercurrent? To me, it seems apparent in your writing that you’ve probably struggled with some degree of depression over the years.

Kennedy: Yeah. It’s probably true. I mean, I used to drink what they call “the alcohol.”

Rumpus: I’ve heard of it.

Kennedy: Yeah, it’s a beverage. And that doesn’t help with the depression. I’m not a super-depressed guy. I’m fond of pessimism. I find it funny. I think a pessimist is basically an optimist with a sense of humor and a heart. You know? I’m working on this script that definitely has this dour wit to it. And I’ve been on this bender of watching Sunset Boulevard and Barefoot in the Park and Philadelphia Story. The dialogue in those movies is so funny and so dark. I mean, the mother visiting Jane Fonda and Robert Redford in Barefoot in the Park—after doing the five-flight walk-up—her opening line is, “If the hardware store downstairs had been open, I would’ve bought something to kill myself with.” Jokes like that are awesome. And these days, it just seems like the cardinal sin in American culture is to play one dark note. It really is. Which is just bizarre to me. And a little bit scary. It’s a big thing in mainstream America. Always be happy, always be happy, always be happy. I think that freaks me out. There’s still points during the week where I will literally think, “That’s right, a lot of other people are on pills and wine and stuff to stay happy. Maybe that’s why that conversation with those three people felt weird. Because I’m not on anything and I’m also not drinking.”

It’s like when you graduate from high school or college, and somewhere in the back of your mind, you’re like, “Well, I guess they’re going to start shutting the high schools and colleges down because I’m done. No one’s ever gonna graduate in, like, 2010. What a weird year to graduate in.” You have that in the back of your mind—I kind of think that about drinking and drugs. I had a beer in August of ’99 and somewhere in the back of my mind, I’m like, “Oh, drinking kind of went out in the summer of ’99.” So then I will literally have a conversation with someone and halfway through the conversation be thinking, What a weird thing for that person to have said. I wonder what that means. What’s the subtext of that? And then I’ll be like, You idiot. That’s a drunk. You’re at a party. They’re drinking. Right, right, right. People do that.

Rumpus: I think that’s a really important thing to remember: that some people have their own hangups and they’re bringing those hangups to the conversation. It isn’t actually you in that case.

Kennedy: Yeah. It probably doesn’t help that…

Rumpus: …you’re analyzing it.

Kennedy: Or that I have lipstick smeared violently around my mouth, with a wig on crooked.

Rumpus: Right. So it’s funnier to talk about death and loneliness and depression and addiction because we never really talk about those things?

Kennedy: Yeah, I think so. And I really have fun with that stuff in writing. People have been disappointed in meeting me before, where it’s like, “Ooh, shoot. I was sort of hoping you’d look like a character out of a Nick Cave song, and live in a dark, tiny room, and you were seventy pounds.” But I say the kind of corny shit that could be in a Coldplay song. I literally look at my girlfriend and I go, “I am just so blown away with the fact that I get to be on Earth. That I get to see things. And see light. And just, like, get to be here.” She’ll just be like, “Oh. Well…good!”

Rumpus: So people must get the wrong idea if they’ve only read your books or your McSweeney’s stuff and expect you to be a guy who only ever talks about dark things. You’re not that guy.

Kennedy: No. It’s funny, if we go to the movies, we’re gonna go see whatever the big comedy is. I mean, my girlfriend is Scandinavian, so she’ll watch Scandinavian movies. You know? And I’ll just be like, “Okay, you watch that, I’m gonna go to the gym. But when I get back, we’re gonna watch Beverly Hills Cop again.”

Rumpus: That’s a common thing, though, right? I think I have an element of this too, where you don’t want to look at things that are going to bring you down. It’s so easy to feel depressed as it is.

Kennedy: Oh, yeah, I totally don’t. Although I will say that one time we went to a [British artist] Lucian Freud show and looked at Freud’s paintings, and they were all so sad that we were cracking up. And we were the only two people in the museum who were laughing. It was so bleak that it seemed like satire. And I will say that I got a real kick out of that. That was just fun. I think, at a certain age, I would’ve been thinking, I have to get out of here. It’s a cloudy day in London and we’re looking at these sad paintings and I feel like I’m gonna freak out. I think I definitely turned a corner somewhere where, if something is so sad, I’ll just crack up. I’ll just be like, Jesus. Really? You created that level of sadness? I mean, there’s so much sad stuff on Earth. You know? Just the fact, like, everyone you love is gonna be gone is enough. And then you spent how many years…what’s this one…it’s a starving dog on a shitty bed next to like a woman who looks lonely, with these weird, tiny breasts? It’s so nuts, it’s funny. It’s fun to crack up.

But then, you read something like Man’s Search for Meaning. You’re sitting there going, “There’s heavy stuff on Earth, and it’s just beautiful and heartbreaking. What are we doing and why are we like this to each other?” But I think that’s what cracks me up about someone saying, “I’m going to make some super-duper-duper sad paintings. Watch this one: I’m gonna start here with a starving…what should it be? Cute puppy, maybe? A starving cute puppy?” There’s something hilarious about that to me.

Rumpus: So you’re a fan of the big comedies like Beverly Hills Cop and you’re immersing yourself in classic comedies. Can you talk a bit about the screenwriting you’re doing now?

Kennedy: Occasionally people will call or e-mail and be like, “Would you be up for taking a meeting and talking?” And usually the general meeting is like, “Would you ever consider writing a comedy screenplay?” And I wonder how I got pegged as the weird Sleepy Hollow character who sits in a little garage, refusing to come down. Yes, let’s write a comedy! I grew up on this stuff.

I was with a friend who wrote a few really huge comedies, and we were at a Yankees game and he just turned to me, wondering if I would ever reconsider. He was like, “Would you ever consider writing a mainstream comedy?” I was like, seriously? I guess to some end—maybe it’s the McSweeney’s stuff, or something—but I definitely went through this period where I was like, “I’ve been trying to do this work for a long time and now you guys are coming to me asking if I would ever consider it, or if I’m too cool for that.” It’s very strange.

Rumpus: I remember seeing something you said about humor needing “higher stakes.” Maybe that’s where these people are coming from, wondering if you’d ever write a farce or a madcap caper or something.

Kennedy: Maybe it is. At least, maybe that’s how they see the question they’re asking. But the truth is, what’s good comedy? Good comedy is about how something funny happened to you on the way to the club. Great comedy is about love and death. So I don’t know. I’ve watched the most mainstream comedies of the last twenty years and I still go, “Yep, love and death, there it is, right there.” I was watching Meet the Parents again yesterday, a favorite. And I was like, Fuck, this is huge: time is slipping away. I’m trying to learn how to love somebody by whatever standards are outside of my head. I’m a male nurse in a family of doctors. And every time I turn around, I’m offending one of these people who—more than ever—I need to befriend, so I can marry their daughter, the only person who has mattered to me.

I think it’s a hilarious movie and it’s one of my favorite comedies. But I don’t see that as not having a vein of darkness to it. It’s a classic. Every single solitary person has felt as alone as that character, while trying to maintain some sense of suburban civility at a family dinner. I see a lot of that stuff as windows start to close. You start trying to step up to the plate and not spend your life alone and you get in those situations where you’re like, Let’s face it—I’m a total alien, a complete mutant. And the harder I try, I push people away that I want to be close to. And I think you could point to ten really good mainstream American comedies that people would probably pretty easily just go, “Oh, yeah, that’s just a cute, breezy movie.” But what are the themes here?

Rumpus: Maybe people are just asking if you think you could write something with a happy ending.

Kennedy: Yeah. I’m not crazy about third acts that just bang you over the head, just clobber you and then play the hit single. But having said that, I like to see the guy get the girl. And I like to see everybody wanting to live happy. You know?

Rumpus: So you’re actively working on scripts now?

Kennedy: Yeah, I’m working on one script. And I just got an e-mail out of nowhere about this TV show I really like, so we’ll see what happens with that. But I hate to say it, because if we all had as much of that stuff happen…none of us would have the time to talk to each other.

Rumpus: You seem like a natural fit to scriptwriting for a lot of reasons. Something I’ve noticed about your writing is that you have such an amazing ear for dialogue. Many of your McSweeney’s pieces and some parts of your books are written in straight dialogue. Where does that come from?

Kennedy: I think it comes from growing up on TV and movies, and joking around with my sister. We would always just take a three-line exchange and repeat it and start cracking up. I think it probably comes from a suburban living room. I think a lot of those McSweeney’s pieces were sort of me, not knowing much about structure yet. Eight years ago, ten years ago, I didn’t know tons about structure, so I literally would just write dialogue scenes. Like: what if a guy was trying to write about sex for a magazine and he had to call four girls and they all went wrong. You know?

Rumpus: Right.

Kennedy: And I think I hadn’t yet learned to be like, Who’s that guy and why’s he trying to do that and what’s the bigger story? It’s not an act and it’s not a story. And I think all this time at The Moth has finally paid off in story arts and stuff like that. I’ve been telling stories and hosting shows with those guys for about thirteen years now, and I think it’s finally just hit this tipping point where I’m like, Oh, wow, well that didn’t take long. Just over a decade and now I get three-act structure. I think most people literally go to a six-month program at UCLA and they’re like, Yeah, I get it.

Rumpus: But there is something really appealing about those straight dialogue pieces, too. Like in your failing at flirting with the hot girl piece, where you can just see the flirting going downhill, instantly. We’ve all had that experience, so we all know the story. And maybe it’s just that the pieces are super bite-sized and readable, but there really is something enjoyable about the straight dialogue in those.

Kennedy: I think one of the best pieces of editorial feedback I ever got was basically, “Take out your description of everything. Get to the scene. Stop spoon-feeding us all of the peripheral observations. Just get to the funny.” I think it might’ve been one of the very first things I tried to submit to the McSweeney’s site, like ’99 or 2000. I had all of these parenthetical observations. And that one really stuck with me. It’s a little precious to be like, “Here’s what I notice about the office where the hot girl is sitting. Before we get to the funny part, allow me to paint a portrait.”

Rumpus: Just get to the funny.

Kennedy: Yeah. Don’t bore us, get to the chorus.

Rumpus: I read an interview where you said you didn’t write much humor until age twenty-six. Was that for McSweeney’s?

Kennedy: Yeah. I mean, I remember it was just a weird time. I lost my dot-com job, I stopped drinking, and my girlfriend and I broke up. So it was like, I really gotta find an outlet. “What am I going to do from 6 p.m. to 2 a.m. in the apartment?” I must’ve seemed institutionalized to those guys, or something. They must’ve thought I was in jail. I was sending them, like, nine things a day. It was the end of 1999, I think, and I had somewhere to put my energy.

Rumpus: And did McSweeney’s lead to other things like The Moth? Was that the progression?

Kennedy: It was weird. Everybody was kind of linked to everybody at that point. The second date that I had with my girlfriend, she showed up at my apartment with a postcard for The Moth. And then another person that I think I met through The Moth was like, “You should check out this McSweeney’s website.” Everybody was weirdly interconnected.

Rumpus: I don’t know if this is still how you feel about it, but I was rereading some old interviews with you, and in one you said that you had never been able to necessarily crack McSweeney’s editorial code. I thought that was really fascinating because, to a lot of people, you’re the gold standard. Whether or not it was a goal, I feel like you’re a guy who has set the direction of a lot of humor on that site. Do you still feel the same way about the editorial code? Are you still trying to figure out what they want?

Kennedy: Well, it’s funny, I think the only reason I ever got stuff on there is because it’s the only place I didn’t try to figure out. Like, I tried to crack it for a little bit and I had tons of stuff rejected. Dozens and dozens and dozens of things. And then I think I got to that point where I just literally had nothing going on in my life. And it was just like such a country song: my girlfriend’s gone, she took the furniture because it was hers, I’m gonna stop drinking and I don’t have a job anymore. And I’m living in downtown New York.

Rumpus: Right.

Kennedy: And I was sending in so much stuff and it must’ve been all getting rejected, I think. And then, I don’t know—something happened. But the short answer is: I still feel that way. I don’t know what the code is. And I never do. For a while at GQ, they were calling me with assignments and sending me all over…and sometimes I would totally stick it and it was just hilarious, how quickly it would run. And other times, it would be two years of just going, “I don’t understand. I don’t understand what you want.” Anytime I stop to try to figure out the house voice of something, I’m just dead in the water. And for some reason, I just got lucky with the McSweeney’s site and never stopped to try and figure out what it is. And if I could do that with everything, I probably would be a lot better off. But when I was writing the HBO pilot for my last book, I definitely fell down that rabbit hole of, What do they want? What do they want? What’s HBO? What are they looking for here? Once you go down that slope—I don’t know about you or anybody else—but I’m dead in the water. As soon as I go down that hole of, Let me try to figure out what they want. I’m sure there are better writers or more astute writers who can go, “Let’s take a minute and try to figure out what they want,” and just nail it. You know? I’ve never been that guy.

Rumpus: Well, it’s also a way of not being super derivative, right? Like, if you’re trying to appeal to what you think the HBO voice is, you’re probably going to end up writing an HBO show that’s already been written.

Kennedy: It’s precisely what you end up writing. And then you end up with a huge conference room looking at you going, “We’ve done this show twice. It was a huge hit for us each time. Once it was called Sex and the City, once it was called Entourage.” And you think, Wow, I really should’ve done what I do. There’s no shortage of the thing that you’re decoding. Maybe the reason that they came to you is that you have another code.

Rumpus: So what’s the status on that show?

Kennedy: It’s one of the more expensive paperweights that a TV channel has ever bought.

Rumpus: Is that paperweight paying your rent now, at least?

Kennedy: Yeah. Obviously, I would’ve been much more thrilled had it been made. But I got to write with a really great guy that I really enjoyed working with, Brian Burns, who is Edward Burns’s brother, who was a producer on Entourage. It was great. I had a lot of fun goofing around with him, and I learned a lot about writing from him in terms of scripts and pace and all that stuff.

Rumpus: I would imagine that all of this helped in your ongoing scriptwriting projects. Does it seem easier now?

Kennedy: It totally does. It seems to be a whole different world. Again, it’s just as simple as, do what you do. It sounds so corny. It sounds like an apron in SkyMall or something—but just don’t try to be anybody but yourself.

Rumpus: Right. By the way, my favorite thing in SkyMall is a little transparent bubble that you put in the middle of the fence, allowing your dog to peer through and see the neighborhood.

Kennedy: That’s such a compassionate item.

Rumpus: Oh, it’s great. It’s for dogs who don’t get to roam too much, but they can look out through the fence.

Kennedy: So sweet. What makes it even more compassionate is that it’s totally in a landscape of self-centered indulgent items, like, how would you like a chair that massages you and prepares a drink at the end of a long, hard day? It’s all these completely stupid, office-based alpha-male, hedonistic items, for the most part. And then, Here’s something that lets a creature see more of the world. Here’s the ultimate heartstring-puller on page whatever.

Rumpus: Have you ever ordered anything out of SkyMall?

Kennedy: No, I haven’t ordered anything, but I’ve always taken great comfort in catalogue copy. With the Internet and everything, I guess it’s more of a thing of the past in a lot of ways. But growing up, I could read catalogue copy forever. Doesn’t catalogue copy make it seem like your wildest dreams are just around the corner? It’s like, I should get a professional-sized popcorn trolley. I have no idea the life that awaits me.

Rumpus: Totally. The girl who got away ten years ago will realize that you have that trolley, which means that you’re really doing really well for yourself. And then maybe she’ll come back.

Kennedy: Yeah. Exactly. It’s like poetry for that American delusion. I was talking with somebody after this Moth show in Detroit last night, about that idea that, in America, you might accidentally wake up wealthy. You’ve been told that for so long. It’s hilarious. The myth since the Industrial Revolution hasn’t been, Do something you’re really good at, something that is really valued at a high amount of pay, and get good at that thing. That hasn’t been the message so much as, Do anything, even if it’s completely menial and dead-end. As long as your misery is at a certain level, you might wind up living on the hill. The most backwards thinking. But catalogue copy reminds me of poetry for that myth. You know? I’m sure I buy into it, too. Like, should I get an electric necktie carousel? I mean, what if I do end up in a life where I have to choose quality neckwear and a large assortment that I don’t have time to manually go through?

Rumpus: It’s like that final thing that you need to actually be happy. It’s amazing that it still works that way. But that’s all you’ll need, that one little thing. It’s kind of like that one pill that will finally make you feel normal.

Kennedy: Yeah. I think it is a big missing piece thing.

Rumpus: You’re right, though. Catalogue copy really is very comforting.

Kennedy: And I don’t know where that comes from. But it does have sort of a mild narcotic feel, right? It’s like someone telling you, “Don’t worry, this world’s not gonna eat you alive. The future holds nothing but comfortable, luxurious surprises.”

Rumpus: Right! I mean, I see that in your parodies of those things, too. It keeps popping up in your work. It’s almost like you have a deep appreciation for that type of writing.

Kennedy: I do. How can you not be kind of a little bit secretly in love with the idea that maybe there is an item that can take away pain? Maybe it’s as simple as a cone for your dog to see stuff, or a popcorn trolley. Somewhere in my heart—and it’s a pretty simple heart—I thought, No, I didn’t feel any pain over my divorce. I have a towel-warmer.

Rumpus: I had an ex-girlfriend get me a machine where you put tap water into it and you push down twice and it fills with Co2 and makes carbonated water on the spot. And then we broke up. And I was like, Well, at least I got this sparkling water machine.

Kennedy: Did you find it an exemption from pain at all?

Rumpus: It was a good distraction, at least. Also, it really works.

Kennedy: That’s awesome. I find that so comforting. It’s really strange. I definitely have that part of me where I’ll often think, What are the most painful things that are going to happen to me in this life? Just make sure that you’re in a first-class seat when you go down. It doesn’t even fucking matter. You know? Like, your father died but no worries! You’re in international first-class! No, it’s still going to be one of the hardest days of your life.

Rumpus: You’ll just have a good place to sit for it.

Kennedy: Yeah, but there’s definitely this part of me that’s like, Would it be as difficult in a good car service?

Rumpus: I think this all nicely ties into your job at Atlantic Records. I’d imagine that there’s something comforting about going to work in a luxurious high rise and working for a record company. Kind of like catalogue copy. There must’ve been something so fun about pretending to be something you’re not for a while, in that it seems different than a typical freelance writer’s day-to-day life, writing in squalor.

Kennedy: Hugely. I mean, it’s again that little piece of me that’s like, Listen, there’s something good here that’s gonna make everything okay. As long as we’re in here, nothing painful can happen. Because look! There’s an espresso machine! And lots of fancy tables and stuff, a cool view, this is happy times! Nothing bad can happen in here!

Rumpus: And it’s not the real world’s problems. The biggest problem is trying to figure out what to write for Phil Collin’s 25th anniversary [an assignment that Kennedy was given and he wrote about, hilariously, in Rock On].

Kennedy: Yeah. But when people say, “It’s cool that you realized it’s not for you.” It’s like, dude, I don’t have any willpower. Are you serious? I’d still be there. I’d be fat, I’d be happy, I’d be saying, “I should try to write a book someday.” I mean, the only thing that saved me is that they laid off 1,100 people. Do you ever think I would’ve walked into my awesome, cool, gorgeous boss’s corner office and said, “Listen, I kind of want to get out there and just try to do my creative things now”? There’s just no way. I would’ve been like, “No, I don’t think I need to go out there and do that. I think we got cool stuff, here. Free things. And neat food. And we all do our fun stuff. We have that meeting where you can see Central Park. That’s neat. I don’t really need to do creative things that much.” When I was walking out the door with a box full of stuff, I was like, Yeah, that’s cool, because it’s time for me to get out and do my creative stuff, anyway!

Rumpus: How long were you there?

Kennedy: A year-and-a-half. I mean, that’s when I was on staff. But I freelanced for Motown and PolyGram and Atlantic since ’98, or something crazy.

Rumpus: So, when things crashed down around you, that’s when you thought you might have a good book on your hands.

Kennedy: Oh, yeah. I’ve said it before, but I got into writing out of financial necessity, which is the biggest irony in the world. But I wrote the first book because I lost my dot-com job and I was like, I need to figure out how to get a check. And I had just done my first show at The Moth. And I was like, Well, I met some people who asked if I ever write this stuff. Maybe I should try to write it down, these stories. That’s the easy version. Of course, it was a year of trying to figure out how the hell to make it work, and I finally fell in it. And then the same thing — when I got laid off at the record company, I knew how long my severance would last and the first thing on my mind was, What happens on this day? When [the severance runs] out? I need to think of something right now. I’ve always just had that sort of blue-collar hustle, or whatever you call it. Even just growing up in the suburbs, I was always the kid who found a way to [say], “How can we make enough money to go to the beach and have lunch after we’re at the beach all day? There’s gotta be some way to do it.” Some hustle.

And so I still think like that. In New York, where it’s so expensive, if I lost my day job at the record company, what’s my go-to plan? All that writing stuff kind of worked. And I’ve said this before, but it’s kind of a weird sadness [about the record industry]. This stuff’s disappearing. I just felt this weird need to record it. This is a really important signpost in American popular culture and I don’t know if people in their living rooms realize it, but this stuff’s just going away. They’re going to make the studio where Stevie Wonder recorded Songs in the Key of Life into condos. You know? And they did. Let’s try to get as much of this stuff on paper as we can.

Rumpus: You did a really great job showing how long people can lie to themselves and others about how things are apparently just fine.

Kennedy: Yeah. Which is weird, too. I had a meeting at Sony Music recently, and I haven’t been up to anybody’s offices since 2004. I had this meeting about a TV show. They’re a music company. And we’re both sitting there going, “Is this right? We’re at a music company. Okay. This is about that TV thing, right?” But I have a friend up there who’s one of the cooler guys I met when I was working in the record business, and I was going up into the Sky Lobby at 550 Madison [the Sony Tower], and I just got up there…and it’s been awhile since I’ve been in those settings and it’s just like, Man! You still have a three-story ceiling on the marble lobby with Mies van der Rohe chairs, and this is amazing. This business made enough cash in its peak that it’s still got enough reserves to be coasting through a decade of diminishing returns. To still have a lobby like this that you have to take an elevator to get to. That’s the only structural thing that that elevator services: Sky Lobby. It’s amazing.

And then I read, two weeks after that meeting, that Sony Japan is selling that building for $700 million. They’re selling 550 Madison. I don’t know—it’s definitely this pang of sadness, of like, God, man. Really? I don’t know. I don’t have a tongue-in-cheek, ironic-guy stance on this thing falling apart anymore. And now it’s actually gotten to the point where I actually have this soft spot where I’m like, Man, don’t sell the buildings now.

Rumpus: Isn’t there a part of you that thinks they just didn’t get it? They still have the elevator to the Sky Lobby. You’d think they could cut back, even just a little bit, and put that money somewhere else. It’s interesting that the old guard is changing and they’ll not recognize it until the building is sold.

Kennedy: Pretty much. But I mean, in fairness, if you or I had a decade-and-a-half of a two-thousand percent profit-margin, or whatever it was, I think we’d probably make damn sure that that’s never going to happen again. As a matter of fact, I would just say, hang on to whatever you have. And if this thing’s sinking, we’ll get off once the water’s up to our chin. Because if there’s one chance in hell that we can ever ride that wave again, let’s try to do it. I’m sure that’s what that business was thinking.

Rumpus: And you get used to a certain way of life that’s probably difficult to give up.

Kennedy: It must be an amazing feeling to hit something out of the park that huge. And just be like, “Oh my gosh, we’re selling these things for $18.99 each? And people will buy it to get two singles? Really? And they’ll buy ten million of them? Wow.” Jesus, that must’ve been a heady thing to have been a part of. How do you walk away from that after the fact? You or I, it’s probably easy to go, “Okay, this isn’t working or that’s not working, let’s branch into that.” But when you’re coming from that era, that’s when you’re just like, I made $180 million gross per release. I don’t know…

Rumpus: Let’s talk more about your involvement with The Moth. I read an interview where you said you just lucked into it. Didn’t you call them out of the blue and the executive director called you right back, even though she was basically calling nobody back?

Kennedy: Yeah, well, it’s the second date I had with my girlfriend. She showed up with this postcard and asked, “Have you heard of this?” And I said no. It was just starting out, I think. And it was at this club on 14th. We walked in and watched this thing and I was naive enough to be like, “I’d like to call those guys on the phone and say that I’d like to try it.” I’m just some guy who worked at a dot-com job. So I just called them up and they had just gotten an office in Tribeca at that point—and I called them and was like, “Yeah, I’d like to try it. I’d like to try the thing you do.” And they’re like, “Well, who are you calling for?” They asked if I wanted to leave a message for the executive director. And at the time there were four people who worked in the office—it wasn’t what it is today. And I think the first mainstage show I did, in like ’99 or 2000, there were maybe seventy-five people there. Last night in Detroit, there were 2000.

Rumpus: Wow.

Kennedy: So, it wasn’t this thing they do all over the country and all over the world. Anyway, it was like a week and they didn’t call back, so I followed up. I was so naïve and weird. It just gets back to that thing of: how many years do you write off to learn how things work in the world? And so I would literally follow up and be like, “Hi, it’s me calling.” And they’d be like, “Who are you again?” And I’d be like, “My name’s Dan.” And then I got a call back, two weeks later or something, and it was the executive director. And one thing led to another and I sort of found myself doing this. And I found out years later that she said at the time, they were getting really, really popular. She would have tons of messages to return. She would have forty, fifty, eighty, one hundred messages a day to return. And she’s talking to her therapist and saying, “It’s overwhelming, and I can’t do a good job at it, and I’m starting to get popular, and we’re in a few magazines and everyone’s wanting to book a show, and I have a hundred messages I haven’t even returned.” And her therapist said, “Just take one call a day and return it and it will make you feel better. You don’t have to be a perfectionist and return them all in a day. Just do one little step per day.” So the one call she returned that day was mine.

Rumpus: That’s insane.

Kennedy: Just that dumb of luck. Now it’s thirteen years later and you’re doing a gig in the south of France and you’re going, Man, it’s fucking weird that she picked that one to return that day because her therapist told her to try it.

Rumpus: It’s amazing. So, with The Moth, was it a good fit for you because of the community and also because of the instant reaction that you’ll get from an audience, that you might not get when you’re writing for the page?

Kennedy: Yeah, I think both of those things. I think it was right around that time where I was just changing up a lot of stuff in my life. And New York City’s a really big city, too, and somehow just right off the bat, The Moth became…I probably don’t make friends that easily, and suddenly I had a community. It’s like the only family I have here, really. All my family’s out West, in California. And every day, it’s just amazing that I’ve met people like this all over the world. It’s pretty cool to be that far from your little apartment and have someone that you feel that close to.

Rumpus: And you said it helped you learn structure. What are your favorite Moth stories, in terms of what they do?

Kennedy: They have a beginning, a middle, and an end. Especially through hosting for the last eight or nine years—I listen to ten stories a night at every show. And even if I’m on the bill at a mainstage, telling a story, I’m still sitting down and listening to everybody else’s story, so you just reach this weird point where you realize…there was a week, not too long ago, where I realized between Seattle, Portland, Cambridge, Boston, and Seattle again, and then doing the podcast, I had listened to forty stories or something. It was like, wow, something is definitely starting to sink in about how a story works. How it works or doesn’t work. A beginning, a middle and an end, all the basic stuff that you’ve heard—but to have a front row seat to watching it work beautifully, or not work, that many times in a given month, has been a really great lesson. And also being on stage and feeling where it works and doesn’t work has been incredible.

But the biggest thing that happened to me at The Moth was the first time I ever told a story about some huge failures in my twenties, about going to Austin and trying to be a singer/songwriter and having it just blow up in my face. I couldn’t really play guitar or write a song—that was kind of the hugest problem there. And I just remember telling it onstage that night and it was getting so many laughs, and I remember thinking that it seemed like this kind of alchemy that could save your life. You could take the things that you were most ashamed of, the things you feel like the biggest loser about, and say them out loud to a bunch of people and hear people laugh. It’s kind of like rehab. There’s definitely this process of: you share the shame, you hear people laughing and identifying, and you leave that night feeling better and not so bad about yourself. And I was like, Oh, maybe I’m not such a lost cause.

Rumpus: I know that The Moth is noteless. Did you have to cultivate a good memory like you cultivated good storytelling techniques?

Kennedy: We do it in day-to-day life. When something happens in your day-to-day life that you find hilarious, or strange, or compelling, or transformative, or whatever it is, you’ll tell your girlfriend, or you’ll tell your best friend, or you’ll tell two people at work and then you’ll do that story, kind of note-for-note, the same way. If you have six friends, you can’t wait to tell all six friends about it. Have you ever noticed that thing in families—where you’ve eaten what you’re gonna eat, you’re done with dessert, you’re having coffee and everyone tells their stories? “Remember the time Dad thought he was lighting the fireworks in the street?” There’s always these greatest hits in groups of friends or family.

Rumpus: What advice would you give to somebody who’s going to present a story for The Moth?

Kennedy: I think the biggest thing is: just try to do the thing you do. When it feels like you just bumped into two friends at a bar or cafe and you have to tell them about something, I think that’s when you’re in the right area. When it feels like you’re hanging around a dinner table an hour after you’ve finished dessert with people you love, that’s probably when you’re in the right area. Tone-wise, feelings-wise. I think the worst thing you can do onstage is just kind of become the medium, the flourish of like, “Allow me to hold my hands aloft to emphasize a tale for you.” It’s just so bad.

And there’s two kisses of death: a lot of times, I see somebody go up and just sort of close their eyes and take a minute to get into a place and then open their eyes and deliver the first line. That’s always an “oh-no-no-no-no-no-just-be-yourself” type of moment. Or the other one is if they come up, and the first thing they do is take the mic off the stand and do that breezy thing where they lean on the mic stand and sort of bob their head with the microphone at chest level to start the story in a laissez-faire sort of fashion. That’s always another “oh-no.” So actually, at a certain point, five or six years ago, we used gaffer tape to tape the mic to the stand. For a while, I would announce it at the start of every show: “Remember, please keep the mic on the stand and please don’t take it off, because we’re trying to record for the radio show and the podcast, and just be yourself and stand and tell a story.” And then it just occurred to us that people would still occasionally do it. And then usually performers who were just showing up to, like, There’s a thing in town that I need to do and get on my resume. So it just to occurred to us to put four feet of gaffer tape around the mic. That saves an announcement. Perfect.

Rumpus: And what about the writing aspect of it, people specifically writing stories for The Moth? Do you encourage them to not write down every single word? Just make an overview, basically?

Kennedy: It’s people like Maggie Cino and Sarah Jenness and Catherine Burns who are really the directors when it comes to the creative side of that. But every time I work with someone on a story, it’s never, “Write this out.” It’s about, “Drop on by and we’ll run it through.” Or, “Give us a call and we’ll run it through, once.” I think that’s the biggest thing, that it should feel like one of those moments where you step out to go get coffee and this hilarious thing happens, and that first person that you have to call and be like, “Oh my god, guess what just happened. I was walking down 4th Street and all of a sudden…” You know, that’s the moment right there. Not so much like, “Allow me to craft a story about a guy I bumped into on 4th Street. Darkness was there. I am walking.”

Rumpus: I would imagine you’ve heard your fair share of that over the years. People just trying way too hard.

Kennedy: I mean, we’re all the biggest dorks at The Moth. It’s not like we’re the cool kids and we know anything that someone doesn’t know. So that’s why I think it’s particularly disenchanting. It’s not, We’re too cool for school and you’re doing it wrong. It’s more like, No, you don’t have to be like that. We’re all just hanging out. Tell your funny thing! Just be you.

Rumpus: Let’s talk about your workday. Have you set up a routine, a place where you go? Do you have certain hours that you work, or is it just all over the place?

Kennedy: It’s all over the place. I tried a lot of that stuff over twelve or thirteen years. I used to keep a space downtown, a desk over at The Writer’s Room, which is kind of like the Grotto. I tried that approach for a while, and it was pretty cool for a bit, and I think it probably jumpstarted some productivity. The ritual. Then it started feeling too cramped and dull and strange and like an office job or something. Then I tried just going through the thing of when you have a couple hours to kill in a hotel on the road, just find a pad of paper and start working on it there. And everything in between.

But you know, when I’m on it, I’m really on it. Like right now, I’m working on this script—I’m on it. I know where I have to be, by what date. I don’t care where it happens. There’s a laptop in the three or four places I could wind up sitting on my ass, killing time in this apartment. So I’m a little less like, “I have to sit in my area and do my thing.” Just open one of these things and start getting stuff down. And there’s pads of paper, and there’s slips, and there’s one big chalkboard wall here that’s got a handful of riffs that will occur to you at three in the morning when you wake up to get a drink of water. I’m just always trying to grab whatever’s around. My life is kind of erratic. I mean, I have weird little OCD rituals that I can’t live without. It’s like, No I have to wake up and walk over and get my coffee at that place. And on Sunday, we buy one of these. That’s what we do. But when it comes to writing, there’s always those writers, right? There’s always those writers who are like, It’s real simple.

Rumpus: Like John Grisham. Grisham was on NPR a while ago saying, “Yeah, I try to write a novel every six months.”

Kennedy: But just because you can, should you? I’m sure he’s a nice guy, or whatever, but I don’t know. Maybe we all could be writing a novel every month. But is that really a good idea? I don’t know.

Rumpus: Do you have any of that impulse in you at all? Where things need to get done and you can’t move on to other things until they’re finished? That impulse that makes some writers stay at their desk until they have their five-thousand words, precisely ordered?

Kennedy: I remember one time when I had to drop something in the mail on a Sunday. My friend and I were hanging out, and he was like, “Why don’t you just do it tomorrow? On Monday?” And I was like, “No, I have to do it right now.” And he said, “Well, if you do it tomorrow, you can get going right now and still make it to the show.” And I was like, “I have to do one thing! I have to drop it in the mail and I need to do it today. Okay?” And he was like, “I…guess. If that makes you feel better. It’s literally not going anywhere until tomorrow, but if you are literally going to feel better, like you did something that had to be done and all of a sudden, things are right in your world because you dropped something over at the post office in the mail on a Sunday, so it can just sit there for twenty-four hours, then I guess let’s do it.”

I remember thinking that that was the biggest insight for me. And I think that’s how I feel about…I guess, if you want to get those three-thousand words by the time you have your fourth cup of coffee and then you go out into the world, you know—terrific, if that makes you feel better. Of course, they may or may not go anywhere. Maybe there are people who are so gifted and feel the urgency of having that sort of laid out in front of them. But I definitely have to back my way into it.

Rumpus: Do you know what you’re going to be working on that day? Like, when you sit down at one of your numerous open laptops in your apartment, do you say, “Today is a scriptwriting day”? Or are you working on a script and all of a sudden you’re writing a McSweeney’s piece?

Kennedy: Almost every one of those McSweeney’s pieces comes from—I’m supposed to be doing something else and, a lot of times, it comes from, like, I’m feeling kind of sad and weird and I want to write something weird and funny, so I don’t feel sad. Or it comes from having to blow off steam because you’re doing that thing, you’re trying to be that person who shows up and gets X amount of work done by X hour, and you realize you literally spent the last two-and-a-half hours staring at Twitter and seeing if there’s any cool, old Jeeps on eBay. You know? And you’re like, Okay, it’s now one o’clock. You’ve been sitting in this chair in the kitchen for three hours now. And at that point, it’s just fun to remember what makes it fun and to go, “What if somebody had to give a thank you speech to a poetry class, but it’s really kind of fucking bitter.” And you just think, Yeah, let’s do that. That’s the moment you unplug the laptop and take it off the charger and move it over to the couch and get a snack from the kitchen. Like, all of a sudden, it becomes fun. Ten seconds ago, you were the Nicolas Cage character in Adaptation, sitting in a chair, staring at a screen, going, “I’m going bald. Maybe I should just quit trying to fool everybody. Who am I fooling? I need to lose weight.” You know, you’re doing that for three hours, and then the second you have this thing of, I just want to fuck around for a minute and do something that’s fun, even though I probably shouldn’t right now. That’s when it becomes…like, oh, now you’re picking up the computer and going over to the couch instead of at the table. Now you’re going into the kitchen, making another cup of coffee. Now you’re kind of excited. You know?

Rumpus: Yeah. And it’ll be fun and funny and you’ll have an audience. Also, you’ll probably get through the piece that day, right? With the longer stuff, everything about that is the opposite.

Kennedy: Yeah. And first and foremost, it just makes you feel better. Don’t you have to do that? You have to remind yourself of that thing of, I remember when this was fun. Remember the thing that got you into it. Those days where you would cut school and just write insane, weird shit and give it to your friends, and you guys would crack up. You know what I mean? That’s really where it started: where you get to the point where you have a script that’s due by a certain time—that’s not to say that’s not fun and that’s not exciting, because it is—but at the same point, I have to sit in this chair like a studious, industrious person for three hours, and I’m getting absolutely nothing done. What if I kind of cut class and write some smart-ass thing over here on the side? And then you come back to it and you’re stoked. You’re like, Now I totally can face this act break and figure out where I’m going again.

Rumpus: It’s almost like you just have to be flexible and patient and if it’s not coming, do something else and eventually it’ll work out.

Kennedy: Yeah, or do that thing where you go, No dammit. You will come now. You will come and there, I have fulfilled my goal and I’m off to Whole Foods. Yay!

Rumpus: It sounds like it’s still fun. It definitely seems like you’ve found something that you really enjoy, in all its different forms.

Kennedy: Yeah. It still feels like a secret. That’s been one of my biggest problems. It still feels like something I’m not really allowed to be doing. It takes me so long to get things done, but I still think I have this idea like, I don’t think we’re allowed to be doing this funny, smart-ass stuff. I don’t think we’re allowed to make smart-ass stuff, because we’re gonna get kicked out of class. I think work is supposed to be somewhat miserable, so this probably isn’t work.

Rumpus: Right. Yet they’re publishing it and encouraging you to do more.

Kennedy: Yes. Hmm.

Rumpus: And do you know immediately when a humor piece is working? Do you ever make yourself laugh with this stuff?

Kennedy: The only time it sucks is when you’re trying to settle a score. Just forget it, if that’s what’s going on. If I’m using my writing as Yelp, essentially, then it sucks, every time. Thank god I’m smart enough to…I’ll be writing and be like, “Ha ha ha, this will be really funny.” Then it’s like, Eh, maybe put that in a folder because you’re just being a dick about what happened to you over at the store. You know? There have definitely been a couple things like that, where I’m trying to settle some petty score with a friend. You’re like, That’s cool. I’ll just write a fictionalized humor piece called, “He Is a Jerk Because He Controls All the Plans No Matter What We’re Doing and No Matter How Many of Our Friends Are Involved.” It just sucks. But other than that, if that’s not happening, then it’s fine.

Rumpus: In both of your nonfiction books, short humor pieces will appear in the middle of stories or between chapters. I find that really cool and fun to read and it’s a nice break from the longer chapters. Does that come from your extensive background of writing short pieces for the Internet?

Kennedy: I think it became a habit over the years of writing on the McSweeney’s site and stuff like that. Now I hear certain things, or look at a really bad menu or something, and I’ll go, “Could there possibly be any less attractive options for food on this menu? Well, what would those be? Less attractive options for lunch on this menu.” I think it’s a nervous tic. So if you’re writing a story, like in Rock On, I’d just get to those points where it’s like, What other lame things could they possibly be telling us right now? And then you list them out. What would that list be?

Rumpus: So overall, it sounds like things are going really well.

Kennedy: Uh, I think so. I don’t know. Yeah. I’m always the last to know and I never believe it, anyway.

Rumpus: Right. And saying it’s going well is always one of those things you don’t want to say out loud.

Kennedy: Yeah, exactly. You know you’re going to be a Paul Giamatti character in two weeks, remembering when you said it was going great. “Remember when I was talking with Jory and I was like, ‘Things are really awesome!’ Now I’m just soaking wet from the rain and I’m just sitting in this Chinese place, watching that girl regard me with disdain.”

Rumpus: Right. Maybe I’ll check back in two weeks to see if you need any assistance. So, after we get off the phone, what will you do? Am I calling right in the middle of a workday? Or is this a non-writing day?

Kennedy: Yeah, this is one of those got-back-into-town-early-in-the-morning-and-came-to-the-apartment-and-eat-candy days. I spend entirely too much time in my day-to-day life going, Fuck it, this is what people do, right? I mean, I’m doing what people do.

Rumpus: Justifying everything. I’m the same way. Right before this interview, I went downstairs to a café and bought a bag of Snackimals, which is a cookie that they mostly sell to four-year-olds. And I just sat there and stared out the window and ate the cookies and thought, It’s completely fine that I’m the only adult in this building eating Snackimals right now.

Kennedy: That’s so much smarter than me. I had lunch with a friend and I fully just took a hard left and went down the old, You know, let’s get some cake. I talk to Jory in twenty minutes…let’s get some fucking carrot cake and maybe a chocolate chip cookie. Or maybe both kinds of cake that they make there. Those are both good. But my idea of being responsible is that I turned it into two packs of Reese’s Peanut Butter Cups and a Ritter Sport.

Rumpus: That’s the great thing about deciding you’re going to eat cake—whatever you get that’s not cake is going to be better for you and you’ll ultimately feel better about yourself.

Kennedy: You’re right. It’s not even a dessert. It’s just a massive justification tool. I don’t even like cake. I’d just like to be able to stab a homeless person and go, Well, at least I didn’t eat cake.

Rumpus: Yeah, I think my rule of thumb with cake is generally wait until after 5 p.m. or so.

Kennedy: But see, they say that’s actually the first sign of the problem, living like you’re living. Instead of the way I do it, which I don’t think about it. You’ve already got a system and rules and shit. That’s like those people who go to a casino and they’re like, “I never take out more than $500 before 7 p.m.” Once all that shit starts, you’re already on the wrong path.

Rumpus: I hear you. So, other than your obvious problems with cake, it seems like things are going well. You have a novel and books and you’re working on a script and you have tons of great work online. Do you feel like you’re becoming more ambitious with what you want to tackle next? Do you have more novels in you? Or are you always trying to vary it up and see how many different types of mediums you can write in?

Kennedy: I don’t know. I’m kind of honestly a little bit surprised by it all. If I had a plan, that would be terrific. I’m not against having a plan. I’m open to having a plan. I don’t seem to have one. But none of this stuff is what I planned, you know. If I would’ve got what I wanted, I would’ve been so sorry by now. I just wanted to be the keyboard player in Billy Idol’s band, or something.

Rumpus: Right.

Kennedy: You know, I still do stuff where I’m like, How did I end up doing this? Why are young people asking me for advice? Why am I standing in a little corridor in a back of a theater, having someone go, “How do I get to do this?” Do what? Seriously, I just patched this stuff together out of tape and wire.

The biggest thing I think, as much as I’ve loved comedy and movies and TV, I’ve somehow not done a ton of that stuff. I’ve somehow been slow to getting around to doing it. So that’s why, between now and when the book is out, I want to focus on doing more live stuff and, just continue talking with these folks who are cool enough to have called from out West. And try to be a bit more honest and show up and try to do work. I think I’ve always felt like I’d be made fun of, or something, if I did admit that I don’t watch Swedish art films. I love Ghostbusters, I love Fletch, I love Meet the Parents, I love Starsky & Hutch, I love Wedding Crashers, and I think I’ve always felt like everyone in this sort of dot-org/podcast/dot-net scene would like make fun of me for loving that stuff, so I think I’ve kept it under my hat for a long time. So I’m trying to be a little more honest about that stuff now. It kind of feels like when I hid Purple Rain behind the Nick Cave records forever, and all of a sudden, I was so bitter at that turn that alternative rock made at one point where it was cool to like pop music. I was upset with myself for having hidden them. And there were three by Genesis or a Rush album in my stacks of stuff when it was cool to be listening to Sonic Youth. I would’ve been mortified. And so, I just felt like I hid that part of myself, musically. So when it became cool for people to be like, “Oh yeah, I totally like Rush!” And I was like, “What? A guy from The Pixies said we could like that?” So I’m trying to do that with writing now, just be open and talking to people who are interested in having me work on that stuff, and not feel bashful about it. Still, you can hear the trepidation in my voice when I’m like, “Sorry if it’s not cool, but I like it.”

Rumpus: And you’ll just keep moving forward.

Kennedy: Move forward. Yeah. I would love to always be writing stuff on the McSweeney’s site. And I love writing books and I want to do that. But also, I’ve completely hidden this other stuff under the bed and I’m slowly starting to suspect that hasn’t been necessary.

Rumpus: Well, this will be the peg of this whole interview, then—the stuff that you’ve been hiding under the bed is finally coming out.

Kennedy: Excellent.

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