David Rakoff

Born: Montreal, 1964.
Currently lives in: Manhattan.
Best known for: His books Fraud and Don’t Get Too Comfortable, his work on NPR’s This American Life, and his essays in EsquireGQ and other, more reputable publications than this one.
First job: “I did one night as a delivery boy for a pharmacist on a bicycle. I was twelve. I lasted one night.”
Currently working on: “A book. But it’s not going so well.”

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Feathertale editor Brett Popplewell recently caught up with David Rakoff in a grimy Manhattan diner just blocks from the author’s apartment. The following is an expanded transcript of their conversation as it occurred amidst the clatter of the busy eatery. A condensed version of this interview can be found in The Feathertale Review 4.

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WAITER: What may I get you?

FEATHERTALE: Coffee’s fine and I’ll have scrambled, please. Sausage and the rye toast with butter.

DAVID RAKOFF: Two over easy with home fries, rye toast, butter. And I’ll have green tea.

FT: How long have you been living in New York?

DR: On and off since 1982. I moved here to go to Columbia University. I did my third year at the School of Oriental and African Studies in London. Then I came back.

FT: When did you begin storytelling?

DR: I was about twenty-five. I was freelancing while working in a literary agency for three years and then when I was in HarperCollins, working in their communications. Eventually I started to be able to pay my way writing, but my extrication from “the day job world” was very cautious and very slow.

FT: What was the first piece you ever had published?

DR: I always thought I would remember that indelibly. I don’t remember.

FT: Do you remember the first story you actually wrote?

DR: Yeah. But I’m not going to tell you.

FT: You say you’d be a dancer if you weren’t a writer. What kind of dancer?

DR: I’d say ballet, but I’m forty-four so I would be a retired injured dancer.

FT: Do you have a favourite humorist?

DR: David Sedaris is one of my favourites but he’s one of my best friends. I love Woody Allen’s early essays.

FT: The kind he used to write in Playboy in the sixties?

DR: I know them from anthologies like Without Feathers and Getting Even. Did they appear in Playboy?

FT: I only know this because I wrote a story for the Toronto Star on the history of men’s magazines and I had to go buy a whole bunch of used Playboys.

DR: That’s probably not something you really want to touch.

FT: Yeah, a shrink-wrapped vintage Playboy.

DR: Hmm.

FT: Anyway, Woody Allen was in some of the issues from the mid-sixties, writing humour essays. Have you met him?

DR: It’s weird. I was blogging about a film retrospective of his two years ago, so I was watching his films every day. And then I went to my friend’s book party and he was walking out as I was walking in, so it was like an odd collapse of my world. Like when you have a dirty dream about a co-worker.

FT: What?

DR: Then you see them the next day and it’s like “Oh.” You know?

FT: I . . . well . . . I suppose I know.

WT: Your food, gentlemen.

DR: Thank you very much.

FT: This looks like it will kill me.

DR: Yes, it will plug up your heart immediately.

FT: Did you care about literature as a child?

DR: My favourite stories when I was a child were The Happy Prince by Oscar Wilde, which is a tale about ultimate Christian sacrifice and death. And The Girl Who Trod on the Loaf by Hans Christian Andersen, which is also a tale of ultimate Christian sacrifice and death.

I didn’t know they were about ultimate Christian sacrifice at the time but I knew they were about extreme humility and being brought low by dire circumstance. Children love that sort of stuff.

FT: Kids love tragedy?

DR: Yeah.

FT: You have a definite style and voice in your writing. Did it just come to you naturally?

DR: There were years where I wasn’t allowed to write in my own voice because I had to be a reporter. It’s not like they hired me for my voice. I was a nobody doing stuff for The New York Times magazine. But the thing that really allowed me to have my own take on things was This American Life, the radio show.

FT: You make some pretty off-the-wall jokes on the radio. Are there any you regret?

DR: There was a cheap joke I made in a piece about watching TV where I joke about watching the real housewives of Orange County where I say “it’s like watching paint dry” and then I say “boring, fake-breasted, Republican paint.” And that seemed low and easy and it threw red meat to the public radio crowd. The moment I got the laughs I felt cheap. There must be other lines, but that one comes to mind.

FT: You say you’re not up with pop culture. Does a part of you feel you were born in the wrong time?

DR: I have, three times a day at least, a deep stab of nostalgia and regret that I never got to see New York in the 1950s. But I have no illusions about nostalgia. I’m a Jewish homosexual. There’s no other time in history when it was all that fun to be a Jewish homosexual. So no, I’m not super-nostalgic in that way.

FT: When are you at your least funny?

DR: I run with a fairly funny crowd. Around them, I’m not funny. I’m nice, I’m kind. But I’m essentially Margaret Dumont around them. The funny’s just being taken care of. I can relax. They don’t need me.

FT: Do you find it stressful sometimes when people expect funny from you?

DR: Yes. But I’m old now. I don’t step up in that way. I don’t feel the need to perform like that.

FT: You’re someone who I would say is pretty accomplished. Do you feel that way?

DR: Ha!

FT: Do you feel that you’ve made it as a writer?

DR: On some level I’m completely aware of the fact that my dreams came true. But it’s not in and of itself enough to have written a book or more than one book or to have had it noticed in a certain way or at a certain level. That’s lovely. But it’s ultimately a bit of a paste jewel. It’s not what really matters in life. I think it can be a bit of a trap to hitch your wagon to that particular brand of star. I think it will ultimately prove itself to be disappointing and shallow and you won’t be left feeling good about the world or about yourself. So yeah, I do hold out hope that there’s something I can do that would meet my fondest dream, like to write a play. But I’m too scared so I’ll probably never do it.

FT: How are your eggs?

DR: Oh, they’re cold. But that’s fine.

FT: When people ask you what you do for a living, how do you answer?

DR: I literally go like this (writes with pen on air) and say: “I’m a writer.” It’s as if I’m asking for a cheque at a restaurant.

FT: What’s the response?

DR: “Oh. Might you have written anything that I would have seen?” I never get the “Oh! I know who you are!” Bottom line, people don’t read anymore. You know? I worked in publishing for many years, so I sort of knew that already.

FT: You’ve also done stuff with Jon Stewart. You’re the voice of Benjamin Franklin on The Daily Show, right?

DR: No, Thomas Jefferson.

FT: Oh, he of less repute.

DR: Jefferson is of less repute than Franklin?

FT: Well, he didn’t invent anything.

DR: No, he only wrote the Declaration of Independence.

FT: Yes, but the slave thing is a bit of a blight.

DR: There is that. But you know, he did actually invent things. I just can’t think of them right now.

FT: What’s it like working with Jon Stewart?

DR: I’ve done The Daily Show four times. I’ve been on Conan O’Brien and Letterman. They’re sort of the same.

FT: When you’re on those shows are you conscious that people are watching you from their bed?

DR: It never even occurred to me.

FT: Will it the next time?

DR: God, I hope not.

FT: Do you work yourself up before going on one of those shows?

DR: I work myself up before every public performance. I need that build up of adrenalin to do a good job. That said I’ve always wanted to be that sort of writer who shows up drunk, swears at the audience and sort of gropes somebody. But I think those days are sort of passed.

FT: Do you think they ever existed?

DR: Oh yeah, I think Capote did a lot of that. The interviews are not entirely planned but you sort of know what you’re going to talk around. The least planned ones are with John Stewart and those are my favourites. It’s the most like a conversation and he’s the one whose sensibilities I think are the most in check with mine. He’s a verbal melancholic Jewish guy.

Your tasks on those shows are to speak in full paragraphs and to be amusing. They’re not going to play gotcha with you. It’s a great honour and a great privilege to be asked because God knows, anyone with a book would love to be on those shows but it’s not like they don’t need you to fill up your seven minutes.

FT: Do you watch a lot of late-night comedy?

DR: No, I don’t have a TV. And they’re on too late.

FT: You don’t have a TV?

DR: I have a little one that I keep in the closet.

FT: How would you describe your writing space?

DR: It’s my desk. It’s in my living room. It’s terribly messy. It’s twelve feet from my bed.

FT: When things aren’t going well, do you crawl back to bed?

DR: No, I eat. I call a friend or I take a little nap or I cook something or I do a little arts and crafts project.

FT: Do you work on a schedule?

DR: No, I stay home every day. I get up at about 6. I go exercise, I come back and then try to work. I’m very undisciplined. I can let entire days go by. Certainly lately the writing has been going very badly, so, I would almost not even call myself a writer right now.

FT: When you get a piece published in Esquire or something do you read it when it’s on the stand?

DR: I used to, but not anymore. Once it’s gone it’s gone.

FT: Do you ever get the urge to just lock your door, take a bag and run away and just never come back?

DR: I used to. The quest for that kind of anonymity – I felt it in my 20s. I still occasionally get flashes of wanting to walk down a street where nobody knows me and where nobody speaks my language and just start up a new life that’s still pregnant with the possibility of adventure. Go to some fucking market with a string bag and, I don’t know – but as I’ve gotten older, and I don’t think my experience is unique the quest for anonymity gets supplanted by and overshadowed by the desire for roots. And it’s far more gratifying and important for me that I can’t walk out of my house or do anything in New York City without running into somebody that I know. But yeah, I sometimes just want to fuck off.

FT: You once said that you were probably the worst reporter on the face of the Earth.

DR: I’m better than I used to be. I still don’t like to ask those things that reporters have to ask whose answers seem both intrusive and obvious — like asking somebody standing in front of the charred remains of their house, “How do you feel?” Like, I can fucking guess how they feel. So in that sense I’m not a real reporter, but I feel less scared — which is weird because I’m scared of everything.

FT: Do you find you learn more about yourself when you’re being interviewed?

DR: Occasionally, but I find I repeat myself a lot.

FT: Let’s try something different. Finish this sentence: “David Rakoff and David Sedaris walk into an Applebee’s . . .”

DR: An animal base?

FT: What? No, an Applebee’s.

DR: Ah.

FT: What happens?

DR: Okay, we sit down — wait a minute, why are we at an Applebee’s?

FT: I went to one last night. I’d never been.

DR: Oh, I went to one in Maine once and I had a basketful of pork chops. It was literally a basket of pork chops served with fried potatoes and it was like a deer lick of sodium. It was fabulous.

FT: I tried to pick somewhere you two would stand out.

DR: So you picked Applebee’s because you thought it was too low for my tastes?

FT: Yep.

DR: Well, my tastes run very high but they also run very low. Like my favourite food is actually potato chips. So, David and I walk into an Applebee’s . . . I’d probably look for that basket of pork chops again. We’d probably just eat our meal and talk.

FT: I’ve read some interviews that people have done with you and they always ask you about David Sedaris. Why is that?

DR: Oh, I don’t really mind it. I owe David everything.

FT: Is he the Fitzgerald to your Hemingway?

DR: Here’s where I’m an idiot — why was Fitzgerald instrumental in Hemingway’s career?

FT: Fitzgerald introduced him to Scribner’s Sons.

DR: I had no idea. Yeah, I guess so. Because through David I met Ira, and then Ira started this radio show and we all sort of went in. David was my entry into that whole world.

FT: New York is a big part of your life and your stories. Do you like going home to Canada and Toronto?

DR: I do, but I find Toronto is emotionally trying. There’s a certain kind of earnestness to it that sometimes drives me crazy — a kind of politically correct humourlessness. But there are parts of Toronto that I really love. I like Kensington Market and Spadina a lot. I used to go to the Art Gallery of Ontario a lot. When I was in high school I used to go to the Bloor Cinema like three times a week. My sister lives around Honest Ed’s. I bought a winter coat at Honest Ed’s once for fourteen bucks.

FT: You probably paid too much.

DR: I think I did. It was clearly a Chinese military coat — ugly as sin, but like a hug. Out of curiosity, how did you get here?

FT: Where?

DR: To New York.

FT: I flew American really cheap into LaGuardia. Wait — is it pronounced La-GAR-dee-ah or La-GWAR-dee-ah?

DR: La-GWAR-dee-ah.

FT: The worst I did lately was describe something as “veh-NEER-ah-bul” instead of, you know, venerable.

DR: I used to wonder why all my friends’ mothers had little boxes filled with index cards beside the stove called “re-kipes.” Instead of recipes.

FT: Do you feel somewhat embarrassed when such things happen?

DR: A friend once said he always felt proud of those mistakes because it meant he was a reader. It means you’re autodidactic, that you’re curious. You should be incredibly proud of it.

FT: Perhaps, though I think “veh-NEER-ah-bul” sounds like a disease.

DR: Yeah, “I didn’t sit on that toilet seat because it was completely veh-NEER-ah-bul.”

FT: You walk out of your house. What do you need to take with you?

DR: My passport. I don’t drive so it’s my only photo ID. A tin of mints from Second Cup — best mints on the market. I buy them in quantity in Canada.

FT: Seriously?

DR: Yes, I keep on fucking saying this in Canadian print waiting for Second Cup to send me a fucking box full of fucking mints. But they never do.

FT: What was your first job?

DR: I did one night as a delivery boy for a pharmacist on a bicycle. I was 12 and I lasted one night.

FT: What happened to the drugs?

DR: Ha! I delivered them. But I was almost prostrate with exhaustion and I quit.

FT: What’s your favourite day of the week?

DR: Thursday because that’s when the food edition of The New York Times arrives at my door. Everything seems possible.

FT: Do you have a favourite poet?

DR: I’m an ignoramus about poetry. I love some Elizabeth Bishop poems. Recently I had to have some acupuncture, and like I said, I’m somewhat of an anxious fellow, so they stuck me with the needles, then they were like, ‘Okay, just stay here and relax.’ And so I was like, ‘Oh, what happens if my heart rate goes up and how am I going to do this? I’m going to have an anxiety attack and how am I going to do this?’ Welcome to my life. So, I recited an Elizabeth Bishop poem called “Letter to N.Y.” really slowly about five times and it got me through. I’m very poorly read, though.

FT: Do you have a lot of books in your apartment?

DR: A lot of people just send me books. I don’t know what to do with them.

FT: What percentage of the books in your home would you have read?

DR: That is such an embarrassing question.

FT: I’m probably at about twelve per cent.

DR: I yearn for twelve per cent.

FT: Fifteen years from now, living the same life?

DR: Fifteen years from now I will be almost sixty. I hope it’s largely the same or the trajectory has proven to be not too cataclysmically reversing on itself or horrible. I mean, there will be inevitable tragedies and heartbreaks, and you know, I hope that I am somewhat at peace with myself as much as I am capable of being at peace with myself.

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