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[posted 03.29.2004]


He calls it Life as a Loser, but the title doesn’t quite do justice to the online column Will Leitch began in 1999 and is ending today. For five years, Leitch has marveled, groused and mused not about being a 20something loser, but about the losses — and lessons — commonly filed under “growing up.” Small-town roots and big-city survival, dotcom delirium and unemployment realities, an engagement derailed hours before trying to Win Ben Stein’s Money and one ailing but plucky cat — Leitch winningly recounted all this and more over 200 columns.

On the eve of the final installment, we caught up with Leitch via email to grill him about the perks of writing online, press coverage of the Life as a Loser book (buy it!) and whether he’d written that last column yet.


Subject: Will Leitch, 28, Libra
Occupation: Writer / Managing Editor, The Black Table
Interviewed by: Samantha Bornemann

1.) It’s three days before your last column is published. Tell the truth: Have you even started it? You’re not gonna deliver some lost-footage, greatest hits type of wrap-up, are you?

I haven’t started it yet. I don’t really know what I’m going to do either. When I had five left, I really mapped it out and thought, “All right, what are the major themes of the series? What do I need to wrap up?” I came up with four major storylines: The Ex-Fiancé, Family, The Impermanence of Relationships and The Resistance to Conventional Suburban Life. I feel like I did a halfway decent job of wrapping those up in the last four. But I have no idea what I’m going to do for this one. I guess it will probably be out by the time this interview comes out, but as of Friday afternoon, March 26, I have no idea what it will be. But it will definitely not be a clip show, I promise you that.

2.) Life as a Loser has bounced around almost as many publications as Will Leitch has. What kept you going all this time? And after 200 weeks, what makes you think you can really stop? Wait, I get it. You’re pulling a Sarah Jessica, a la Sex and the City, deciding to go out while you’re still in readers’ good graces. So is there a movie on the horizon?

Honestly, it’s just time. There are so many people on the web right now just writing about their lives, personal essay stuff, that it’s exhausting even me, and I’ve been doing it for five years. I’m working on my second book right now, and it’s fiction. I’m tired of hearing about myself, I’m running out of stories and, deep down, I don’t think there’s a huge clamoring for that many more. My biggest fear is that the column would become a parody of itself, where I was just desperately trying to come up with a story where I get hit in the nuts or some girl pours water on my head.

Not to sound bad, but I think the last 10-20 or so columns have been among the best ones I’ve ever done. I do kind of feel like I’m going out with my best stuff. If that’s going out on top, great. But I have a whole other book to finish right now, and besides, 200 is a nice round number. Assuming, of course, I actually write No. 200 this weekend.

And if there’s ever a movie of Life as a Loser, the Janet Jackson pundits will be right: Our cultural landscape will indeed be a barren wasteland.

3.) OK, so you’re really done. Whose writing do you recommend we turn to now?

Well, The Black Table should be required reading, obviously. (Even though I’ll still be writing stuff for them.) I’m really into Chuck Klosterman these days, actually; his column in Esquire is worth a subscription all by itself. Tom Perrotta’s new book is incredible, and I’ve been enjoying Eggers’ work on Salon lately. As for websites, The Simon, Knot, Flak, Yankee Pot Roast, Morning News and the great are all daily rockers. But The Black Table will save your soul.

4.) Column readers know a good deal about your work history, your relationship resume, the ups and downs of your bank account, your drinking problem and your masturbation habits. Actually, we know more than enough. But we don’t know how the column has affected your everyday life… The Will who comes across in your columns is quite specific: adamantly Midwestern, preoccupied with sports and, to a lesser extent, girls, lurching and bumbling toward… some semblance of Manhattan adulthood. How close is that Will at the keyboard to the Will who walks and talks to co-workers, waiters, friends and the like? And has your lack of anonymity prevented you from really baring all online?

I have a pretty hard and fast rule: I don’t discuss whatever I wrote in a previous week’s column with my friends. Sure, I might talk with another writer friend about whether or not a particular week’s column “worked” or “blew,” and we’ll debate different little techniques to try or strange jokes that might or might not have landed. But I’ve been pretty steadfast in trying to make sure the column never became an online diary. I never wanted it to be a log of what’s going on in my day-to-day. If biographical information has come out in the column, it has been a by-product of what I’ve tried to do with the column, which is to take a certain experience, or a certain feeling, something that feels specific to me but is probably shared by everyone, and express that. Like everybody, I’ve had troubles with the opposite sex, I’ve struggled to communicate with my family, I’ve spent days wondering, when I look at myself, if this is really all there is. I think we all do that. That has been the goal of the column.

In real life, I’m certainly a lot less interesting than the column might make it sound, because I select anecdotes or experiences I’ve had that I know will have some sort of universal appeal. In real life, I drink too much, watch too much sports and don’t sleep enough. These are three trivial, boring activities, and they don’t contain much inherent drama. I have to pick and choose which of my experiences are relevant enough to write about; most of what I do is pretty dull.

But certainly, people have been offended by things I’ve written, particularly girlfriends, who, get this, aren’t too crazy when their boyfriend writes 2,000 words on having sex with another woman. I’d like to say I’m understanding about this, but I’m really not; they pretty much just have to deal with it, or leave. That’s mean and unfair, but that’s just the way it works. This column isn’t for me, or for them. Fortunately for anybody I date in the future, they don’t have to deal with the column. But I have to write what feels true, not what might or might not get me in trouble. It’s just part of the deal.

5.) Some girls are notoriously game for fixer-upper boyfriends. How many women have you lured in by playing the loser? [Plus: Back in 1999, when the column was still young, you wrote that you’d kissed 19 girls. What are your stats now?]

I’m not going to pretend that I have never had an experience with a woman that was not at least indirectly related to the column. When I wrote that column way back when, of those 19 people, not a single one of them knew the column existed when they kissed me for the first time. Since then, that number has risen to 41, which, over a five-year span, is normal, I think. Of those next 22, all but three knew the column before they knew me. I think the main reason any guy does anything, really, is to meet girls; the only thing I know how to do is write, and if that’s appealing to a girl, and I’m attracted to her, jeez, it’s hard to meet people, you know?

That sounds kind of sketchy, I know. I don’t make a habit out of it or anything, but yeah, it has happened. (So send your pics, ladies!)

6.) I appreciate a thorough answer. Did you pause to chart this out, or do you still have those stats at the ready in your head?

I will confess, I still have my list. Whenever I kiss someone new, the first thing I do the next morning is add their name to the list. That sounds bad, but it’s true.

7.) There’s nothing like a column about a dying pet to bring on the audience waterworks. Did you ever get another cat after Wu-Tang?

You know what’s funny? Wu-Tang survived. He really did. I wrote that column knowing that he was going to die, but after I filed it, he got worse. Even though the vet told me that surgery would likely be a waste of time and money, I couldn’t help it. He was crying really loud and was in a lot of pain, so I took money that I didn’t have and paid for the surgery. And it actually worked.

So he’s alive, and happy, and thank heavens for it. I need that guy around.

8.) Never mind that your book is nonfiction; it seems the Associated Press found it convenient to anoint you spokesperson for lad lit, and the rest of the media will follow. Is this a label you’re comfortable with? What authors’ work do you think is most similar to your own?

Well, it’s just a label. We had the primaries here in New York recently, and I’m a registered Democrat, which you have to be in order to vote in the primaries here. I asked a friend of mine if he was voting, and he said, “No, man, I don’t like to be labeled.” I looked at him like he was an idiot. Who likes to be labeled? I still want to vote.

That’s how I feel about that story. It’s obviously an honor to be lumped along quality writers like Kyle Smith, and the exposure has been great. Is what I do “lad lit?” I don’t think so, except to say that it’s literature (an arguable point) written by a man (also arguable). But everything in that story is accurate, and if it helps people find my stuff, it’s great. But I certainly won’t be going around saying, “Hey, everybody, I’m writing lad lit!” I’m a writer, and obviously anything that gets people to read and react to my stuff is great. I’m not going to complain. But I’m not sure I’m part of any huge trend or anything.

I don’t think there are many writers like me, and thank god for them. I’ve certainly aped plenty of writers, though; Tom Perrotta would have to be pretty near the top of that list. When you think of what he does, and how easy he makes it look, it’s staggering, and definitely humbling.

9.) So what’s with that backdrop on the AP photo? You’re seated before a cozy fireplace, wearing a leather jacket — it that where you live now that you’re a fancy book writer?

That picture was taken at a hotel across the street from my office. I not only can’t afford a fireplace in my apartment, I can barely afford a heater.

%(qst)10.) In addition to your day job, you’re managing editor of The Black Table. What’s so satisfying about journalism on the web? %

There are no limits. I wrote a story about Dennis Kucinich’s fledgling presidential campaign that ran about 6,000 words; I wrote a baseball preview that’s about 10,000. That doesn’t mean you have to be indulgent; it just means that you have the space, the freedom and the wherewithal to do what you want to. Anyone and everyone can see it at any time. It’s cheap, it’s simple and you can do everything you can at a print publication — and a lot more. I don’t know why there isn’t more, actually. I still get responses about the Kucinich story, and it ran almost a year ago. That would never happen at a print mag.

11.) If your dream job is novelist, what’s your dream journalism job?

Well, it is to write novels. The goal is to get to the point where I can live comfortably while just writing all the time. That’s anybody’s goal. But my dream journalism job? I’d like to write a yearly book about the St. Louis Cardinals, just following them around. At the end of the year, I’d write a big huge book about the experience. It’d be tough to beat that.

12.) I’ve written about personal events a few times over the years, and I find that there are some pieces I can enjoy returning to, as a means of reliving the event or merely refreshing my memory, and some that I know — by title or first line — that I don’t emotionally want to revisit. Do you find this is true for you? Or have you avoided rereading your published columns (other than for the compilation of your book)?

Recently, as the series comes to an end, I’ve found myself going back and reading some of the old ones. It’s easy to distance myself from whatever might have been going on personally, since there are so many of them now. I’m able to realize which ones were funny, which ones were indulgent, so on. I never thought I’d be into that; the column used to be so close to me, I couldn’t get that perspective. But now, I recognize that it’s just work, that this has been a process to try to make me a better writer. I think it has succeeded, particularly when you see how bad some of the early ones are.

I’m curious to read them in 10 years. I have a feeling I’ll think every single one of them sucks.

13.) I love that you wrote a column about the Oregon Trail. That game rocked, and I can’t believe teachers thought it was an educational activity. I couldn’t even pronounce cholera for another five years or so… Anyway, what’s your game of choice these days?

Ha. I’m addicted to Outburst, and have been so for many years. It’s like Family Feud played really, really fast.

14.) You’re not quite 30 yet, right? How different is late 20s from how you thought it would be — what you thought you would be — back when you were in school in Mattoon, Illinois?

I am 28 and have a LONG TIME UNTIL 30, thank you very much. Ahem. I have to say, growing up in Mattoon, I assumed I would be married by now and have at least one kid. Instead, I’m wearing an Albert Pujols jersey, screaming at the Illini game and then falling asleep in a chair with a vodka tonic in my hand. Deep down, I like where I am now. But feel free to check back in a couple of years. I reserve the right to be wrong.

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samantha bornemann is a chicago-based author and editor. you can read more of her tv and film criticism at and in the book neptune noir.