2007_06_david_rakoff.jpgDavid Rakoff is the author of the hilarious and best selling essay anthologies Fraud and Don't Get Too Comfortable, countless articles that have appeared in publications such as Vogue, GQ, and Salon, and has contributed to NPR's This American Life. Gothamist sat down with the writer to discuss his genesis and his moments of doubt.

Why did you start writing and how did you pursue it?
It all comes out of a bullying and narcissistic blabbermouth tendency, I'm afraid. A conviction that I should be heeded, in some way. I think that characterizes the impulse to write for most everyone, although sometimes it's couched in more charitable terms as "having something to say." What I really wanted to be was an actor, although it was so frowned upon in my family that I only ever pursued it in a half-assed way. I did downtown theater wiith friends while at the same time, I was also writing freelance (and working full-time in book publishing for well over a decade. So much energy. Now it takes a full day to get the cereal bowl over to the sink). It's a great privilege and almost narcotically pleasurable to be listened to. Eventually, the worked accumulated to the point where I was able to make it my day job, which happened nine years ago, which seems both an instant and an age.

What sort of writing did you do in your youth and how dedicated were you in terms of writing growing up?
Having expunged my childhood from my memory (my upbringing was charmed and lovely, but I myself was awful and neurotic and unpleasant and best forgotten, so...poof, Gone!), it's pretty much conjecture on my part. I was always up to something, although not dedicated, I don't think. I had many hobbies, all artistic and faggy, to be sure. I still do little art projects. If you opened my closets and saw all the supplies, you'd think I ran a kindergarten (that, plus all the five-year-old children with duct tape over their mouths...).

What were your reading habits like growing up?
I think I read a fair amount, but who knows....When I was very young, I do remember that my two favorite stories were "The Little Girl Who Trod On A Loaf," by Hans Andersen, and "The Happy Prince" by Oscar Wilde, both of them grim tales of sacrifice, privation, death, beauty, and a creeping Christian moralism. They both preached a kind of abstemiousness that left me with breathless with penitential rapture. In the first story, for example, a proud girl defiles some bread-the staff of life-by stepping on a loaf of it floating in a puddle in order to protect her pretty shoes, and so, vain and venal creature that she is, the loaf sinks down to hell with her on it! The Happy Prince is about a swallow who falls in love with a jeweled statue. The bird picks the gems and gold leaf off the prince and distributes it to the poor of the town and, her work completed, freezes to death. Loved that.

What was the first piece that you ever had published?
Again, I always thought that I would remember such a thing with absolute clarity but I'm embarrassed to say that it's a bit foggy. I think (I think this is right) it was a piece about Merchant-Ivory whose "Slaves of New York" (a major bomb based on the Tama Janowitz stories, starring Bernadette Peters) was about to come out and they spoke at the NYU Business School. The piece was for some internal newspaper at the university. I was never an NYU student, but my friend's mother edited the school's, ahem, organ, and pushed some work my way in order to augment by about fifty bucks my annual salary at that time, which was $13,000, a sum that really only makes sense if it's 1938, which it emphatically was not. So, I think that was it, but I also vaguely remember telling myself that it didn't count as first-piece-published because people couldn't buy the periodical (I can always find a reason to downgrade something).

Was there ever a moment, or moments, when you'd doubted your own abilities as a writer and how did you work through them?
I've written one book called "Fraud," and another called "Don't Get Too Comfortable." I think the question is more properly posed as, Is there ever a moment when I don't doubt my abilities? Almost never. Retrospect has turned out to be a less fevered state, I'm happy to say. With a little time and distance, I've been able to stand reading what I've written, but in the moment, never. It's all shit.

What are some projects that you're currently involved in or contemplating?
A film script with my friend Dave Hill, and the dreaded prospect of a third book. Plus various little freelance assignments. I'm writing a piece right now for Radar Magazine about tween culture. I just watched High School Musical and now I want to put my head in the oven.
The premise for the film script is that I am an author named David Rakoff, touring for a book called "Don't Get Too Comfortable," a collection of humorous essays about our culture of excess and our lovely First World Problems. Dave Hill is the publicist who escorts me on said tour and I am a passive-aggressive, high-maintenance monster throughout (a character I don't have to labor even one second to access, I am sad to say.) As for the status of that project, who knows? The film world is a hugely foreign country to me. Things seem to be proceeding apace but it's all so theoretical.

Please share your strangest "only in New York" story.
I always wanted to do a parody of the "Metropolitan Diary" that runs every Monday in the Times where those quintessential "only in New York" anecdotes always seem to revolve around class and privilege: precocious children having to be taught that pudding is not dissimilar to mousse, altercations in the salmon line at Zabar's, etc. I can't really think of any of my own, alas. I have lots of stories of being the keeper of many terrible secrets or beiing an observer of many instances of infidelity and how small a town this really is, but that's hardly a New York trademark, I don't think.

Which New Yorker do you most admire?
I have a lot of New York heroes: Dick Cavett, Grace Paley, Gail Collins, Woody Allen (a cliché, but what can I do), Meryl Streep, Isaiah Scheffer up at Symphony Space, public school teachers, doctors who take insurance, librarians.

Given the opportunity, how would you change New York?
All my dreams are incredibly naive. I have a child's understanding of market forces and real estate, but I've been despondent over the city's extreme affluence. I understand how hospitable New York can be to the aspiring hedge funder, but I cannot for the life of me figure out how young people with dreams of making art are even managing to come here any more. And without them, the city will become like everywhere else. More subways, fewer cars, maybe? Affordable housing, blah blah, perhaps a more mindful approach before we efface the neighborhoods and districts that provided specific services and made the city unique and perfect and replace them with open-plan loft condos all sporting the same Wenge-cabinetry kitchens, for god's sake. New York is breaking my heart. I've often said that it's like having a really interesting boyfriend suddenly becoming really, really into wine, and having to have endless conversations about it.

Under what circumstance have you thought about leaving New York?
It's always a fairly terrible scenario involving family tragedy and elder care. Otherwise, I can't imagine living anywhere else. I don't think people would like me anywhere else. They don't even like me all that much here, as it turns out.

What's your idea of a perfect day of recreation in New York?
I'm a cheapskate and obsessed with the city, so I like things that comprise being free and New York history. Take the Staten Island Ferry just before dusk. Free, first of all, and there and back gives a breeze and a view and kills an hour and you return as the sky is turning navy. Walk up through the Wall Street area past Fraunces Tavern, Stone Street, and India House, past Federal Hall, then go to Chinatown for supper. I've lived here twenty-five years and still look up like a tourist. I keep on meaning to go back to City Island for a cheap lobster one of these days, ditto Coney Island before they tear it down and turn it into-surprise, surprise-open-plan loft condos all sporting the same Wenge-cabinetry kitchens. But if I had unlimited funds, maybe the perfect jewel of the Neue Galerie, the German-Austrian art museum on 86th street, followed by a drink at Bemelman's bar in the Carlyle Hotel.