leitch_big.jpgThe Basics
Age and occupation. How long have you lived here, where did you come from, and where do you live now?
I'm 28, I co-edit BlackTable.com, write for a financial magazine and am writing a second book. I have lived in New York for just over four years. I grew up in Mattoon, Illinois, which has about as many people as two cars of the F train during rush hour. People still burn their trash there. I live in Boerum Hill, on Smith Street in Brooklyn. If you live in the neighborhood, I apologize; I'm the one playing the tuba all hours of the night.

Three Wishes
1. It is my limited observation that the people who pass for the damaged-beyond-point-of-repair term "hipster" in NYC are actually all from the Midwest. What do you think?
Well, honestly, is anyone here actually from here? Sure, there are a few Bay Ridge stragglers roaming around, but, other than people from Bay Ridge, does anyone consider Bay Ridge New York? I think most Midwesterners here are of the closet variety; when you ask them where they're from, they put their heads down, nod softly and wait for you to go away. I believe Midwesterners here should be prouder. At least we didn't grow up in New Jersey. Anyway, your question: No. I think people who pass for "hipster" are all from New Jersey. Or maybe Connecticut.

2. "Life As A Loser" - is it ready to be a movie or TV series? Who would play you?
What a frightening thought. Didn't they already make "Herman's Head?" I think I would be played by Kate Bosworth, or maybe that surfer lady with the one arm. Lysette Anthony, or possibly Blair Underwood. Actually, Peter Dinklage could pull it off.

3. Digging through your archives I was happy to find you share my confusion for the band Phish. Can we really win against these people? Will future generations be safe from this crap by the time they reach college?
We are winning. I mean, aren't those guys, like, 60 by now? And it's never a good sign when your bassist is taking secluded "art photos" of nine-year-old girls. (Now that, my friend, is Strong Weed.) These guys have an enemy in the Hell's Angels. All we have to do now is just sit back and watch. Here's some popcorn.

Proust-Krucoff Questionnaire
Please share a personal (and hopefully interesting) NYC taxi story.
I once shared a cab from LaGuardia to the West Village with some lady named Alexis. She was telling me about her trip to Miami when, mid-sentence, she vomited all over the back seat. The driver, who thought she was with me, started screaming at both of us and demanded we get out, right there on the BQE. I explained that we were just sharing a cab, I don't even know this person, and amazingly, he listened and understood. So he just kicked her out and left me. And she even gave me 10 bucks! That day I learned: Whenever someone sitting next to you does something stupid, deny all knowledge of their existence and slink away, whistling. This comes in handy.

9pm, Wednesday night - what are you doing?
Sitting outside Woody Allen's house, waiting for the nanny to leave. She usually doesn't get out until 9:15, but I like to get there early.

What's your New York motto?
Shut up and get to work. No. That's too harsh. Let's hold hands! Naw, mushy. How about "Two blocks up, two blocks over." That's good. A guy I used to work with would give that exact advice whenever a tourist asked him for directions, no matter where they were or where they were trying to go. He was kind of a dick, actually.

Best celebrity sighting in New York, or personal experience with one if you're that type.
I once waited in line behind Michael Musto to see "Requiem For a Dream" on my 25th birthday. He turned around and asked me if I was old enough to see this movie. A sweetheart. Oh, and I once got yelled at by the guy who plays Artie Bucco on "The Sopranos" for bumping into him on the Q train. I thought he was just a random jerk, and I turned around, angrily, and then, right his face, yelled "Hey, the Vesuvio's guy!" He actually smiled and said, "Yeah, that's me!" He must not get recognized very often.

Describe that low, low moment when you thought you just might have to leave NYC for good.
Jeez, which one? All right, we'll go with the time when I was living with a girlfriend who hated me, sleeping on the couch, broke and eating cat food. She would wake up in the morning, throw something at my head and say, "I'm going to work. I'm sure you would do the same, but you're useless. Try not to stink up the place today." At that point, New York seemed like quicksand. I actually had bought a bus ticket to go back to Illinois. Mercifully, I found a job shortly thereafter and was able to stink up my own place.

Just after midnight on a Saturday - what are you doing?
Sitting outside Woody Allen's house. The lights usually turn out about 11:15, but sometimes Soon-Yi will stay up and read. She sure does love John Grisham!

What's the most expensive thing in your wardrobe?
I have a Catholic priest's sacrament robe that cost me 100 bucks. Did you know you can go to religious stores and just buy those? You don't need, like, a priest's license or anything. It's fantastic. I like to wear it downstairs to buy chocolate milk and Hustler.

Where do you summer?
In my drippy, oppressively hot apartment, praying for a death that will never come.

Who do you consider to be the greatest New Yorker of all-time?
Did you know that Woody Allen shops at Gristede's? I wouldn't have expected that. In fact, I haven't seen him go to Zabar's once!

What was your best dining experience in NYC?
When I was really poor, I would go to the Gray's Papaya right across the street from my office and eat two hot dogs and a Papaya Juice (whatever that is) for two bucks. You can't beat that. I think I ate that every day for a year.

What happened the last time you went to L.A.?
I saw Rhea Perlman, walking down Rodeo Drive, slap her child for crying. Carla! Heavens!

Of all the movies made about (or highly associated with) New York, what role would you have liked to be cast in?
I would have loved to sat next to Timothy "Speed" Levitch during "The Cruise," and interrupt him, after every statement, with, "Um, what are you talking about? Are you ever going to get a real job? Don't you think you should cut your hair?" Would have driven him nuts. That would have been fun.

If you could change one thing about New York, what would it be?
Well, outside of the obvious (subway shuttles to the airport), I would love for Mayor Bloomberg to require that Woody Allen live right across the street from me, where he would make me tea and we would talk about Bergman films, every morning. Oh, oh, and he'd have to tell me what it was like to do it with Diane Keaton.

The End of The World is finally happening. What are you going to do with your last 24 hours in NYC?
I'm going to watch all 24 episodes of "24." I've been meaning to get caught up on that show.

Will's first book, Life as a Loser, is available for purchase here.