FIVE FOR WRITING: DREW MAGARY!

I don’t know Drew Magary. I know his writing, mostly through Deadspin and Kissing Suzy Kolber. I can’t remember how I came to read an advance copy of his first novel, The Postmortal—I feel like he whored himself out to me, but I might have pestered him, because he’s one of those guys I’ve always wondered about, and not just in a metaphysical sense. Either way, it doesn't matter: The Postmortal is good. Really good. I’ve already attached myself to write the screenplay (I’m not sure if Drew knows this yet) for what will surely be a popular and critically acclaimed blockbuster about immortality, the meaning of life, and women with impossible bodies.

You can pre-order your very own copy here.

What’s weird for me about this particular Five for Writing—apart from its comparison of personal watercraft to breasts—is that I actually found it kind of unsettling. I’ll write more about this later, but I felt like Drew was speaking to me when he wrote what he wrote about guys who write on typewriters. I like to think writing is IMPORTANT, because it’s what I do. But maybe, when you strip it right down to its most basic elements, it’s just putting words in an entertaining order in exchange for money. Reading this made me wonder whether I’ve been squeezing the bat a little too hard lately.

Anyway, maybe a little more than usual, I’d like to thank Drew Magary for joining the Five for Writing circus. Despite the fact that he puts two spaces after every period—fixed—I really like what he wrote here, and what he wrote between the covers of his new book. I hope you do, too:

1. Don’t take this the wrong way, Drew, because there’s a compliment in here somewhere (really): In some ways—and by some ways, I mean in all ways—you seem an unlikely writer to come out with a thoughtful, philosophical, poignant novel about the perils of immortality. I mean, your first book was called Men With Balls; one of your more widely read essays on Deadspin was called “Fuck You, Charlie Brown.” And now… This?  The Postmortal? A novel? I read the first page and I felt like Simon Cowell watching Paul Potts singing Nessun Dorma.* How could this possibly happen? How did you go from there to here?

I was laid off from my job at an ad agency back in the spring of 2009. And when that happened, I went and asked a guy I knew at NBC for freelance work. And he said to me, “We can give you work, but it’ll be in the fall.” And so I had this summer in front of me where I knew I’d have time to work on some bigass spec project if I wanted to: a novel, a screenplay, a TV series idea, a book proposal, a recipe for a new kind of chocolate peanut butter, etc. So I knew I’d have to get something done in that relatively short window, and I wanted it to be something that offered a potentially large reward somewhere down the pike, financially speaking. Because I have two kids and they’re expensive as shit.

So I had a few ideas, but the idea for the novel was the one that seemed to take off in my mind. That happens sometimes. You get an idea, and it just starts metastasizing in your brain. And you figure, “Well, this is where I should probably go.” So I went to the library every weekday with the goal of banging out 2,000 words a day or so, so that I’d have a working draft by summer’s end. And the more I wrote, the more the ideas came rushing out, and so I tried to get them all down as fast as I could and then worry about cleaning it up later.

The lesson I learned from Men With Balls (Other than, “Holy shit!  I can write a book!  NICE!”) is that people don’t really buy sports books. Unless your name is Bill Simmons, you’re not gonna get rich selling stupid toilet books filled with sports jokes. And unless your name is Jon Stewart, people probably aren’t buying your humor book, because they can get humor from the web. You have to do something bigger and more substantial, something that lets people know that there was a great deal of ambition and care involved. So that’s why I never bothered writing another book like that and I probably never will, even though I like it. Men With Balls didn’t have any recycled blog content in it, but the tone of it was the kind of thing you could get from me pretty much any day of the week for free, and so I think that’s a barrier to getting people to buy it, rather than an enticing proposition. Also, it didn’t appeal to ANYONE outside of people who already read Deadspin and KSK. And that had to change. I had to try and shoot for something that hit a bigger target. 

If you blog long enough, you quickly figure out that, even if you pull a big audience, blogging isn’t a very lucrative form of writing. [Ed. note: Shit.] The most financially rewarding kinds of writing are original stories, stories that can be extended into movies and TV and graphic novels and everything else. You see something like Harry Potter and, as a story, it operates as its own little economy. The story is strong enough and written well enough that it can support all these other accessories and iterations, and that’s really where you have to go if you want to write for a living and not starve to death by age 50. Because I’m not gonna be cool enough to blog for much longer. I’m not gonna be able to keep up. Someone always comes and knocks you off the mountaintop. You have to evolve and you have to go somewhere new before the ground underneath you falls out. So that’s what I tried to do. It was a strategic business decision, but it was also a good enough idea that it kept me awake at night sorting it all out. That’s usually when you know you have a good idea—when it fucks with your sleep.

And it’s not like I haven’t written seriously before. I’ve written serious things at Deadspin and KSK before. Not as often, of course. I just follow whatever decent idea comes up, whatever idea I think I can work with. Usually, that idea is comedic, but not always. This just happened to be a more serious idea. I don’t really prefer one genre over the other or anything. I don’t sit down to write a serious thing and be like, “Now, they’ll see a side of me they’ve NEVER seen before!” I’m just trying to get down whatever the best idea is, whatever will keep people reading. That’s why this book has lots of sex and guns and stuff. Sex and guns are WILD.

2. *I referenced pop culture here, and I want to punch myself in the face for it—because I think pop culture references make potential literature seem too much like fashion or a reality TV fad. They make writing seem temporary. (I always wonder what someone reading one of our stories in twenty or thirty years will know about Britney Spears; I’ve never read a Gay Talese story that made a witty jibe about Jim Croce, for instance.) But, of course, that also means I’m pretentious enough to think that anyone will be reading my stuff any length of time from now. A lot of your writing has been for an online audience—an impermanent-feeling medium. Writing a novel—especially one about immortality… Did you ever feel as though you were writing something more lasting than you might be normally? Did you think of this book as a more permanent reflection on your ability? I don’t know about you, but I think of novels as the closest things to monuments that writers can build. I like to think words might live forever.

Sure, it’s a novel, so you take it much more seriously than a blog post about what a dipshit Peter King is. Books, obviously, have longer lead times than blog posts, so for that alone you have to adjust and make sure that what you’re doing won’t feel dated and pointless the instant it’s out there. And of course the publisher has all kinds of copy editors and production editors who go through the book very carefully and point out all the places where you fucked up, so the end result is much more polished and professional looking than what you get on a site that was written quickly and barely edited. Blogging SHOULD be like that. It should be sloppier. It should feel more like a daily conversation. It should feel fresh. A book is different because you’re asking someone to stick with you for 300 pages and 10 hours or whatever, and you aren’t giving people a chance to comment. So it’s hard for people to read it if you’re just dicking around the same way you do online. You can’t treat it quite so casually.

That said, I try my very best to not get into the whole “writer with a capital W” mentality, like these dipshits out there who only compose on typewriters while wearing cable knit sweaters and shit. As if they’re the recorders of the human condition or something like that. My only goal is to keep people entertained and to occupy them from doing shit that’s way more important than what I do. If they find meaning in it along the way, that’s a nice bonus. But just involving people is the main thing. I think it’s really easy to fall into this mentality where you’re a Big Writer with Important Ideas and a Big Dick, and the second that happens you become unbearable. You can see the strain when people write like that. Just read any review at Pitchfork.

I’m not immune to that egotistical thing where you write a book and it’s like, “Now when I die, my words will live FOREVER!” But I know, deep down, that’s just a load of shit. It’s a way of boosting your pride and allaying your fear of dying. Words don’t live forever, and neither do you. Some books may become classics that are perennially read, but Shakespeare is still fucking dead. The fact that people are reading Hamlet now isn’t doing his corpse much good.

3. You’re a husband and father with many responsibilities and a desire to maintain your impressive weight loss. How did you approach the actual writing process? Did you write at regular hours or just whenever you could catch a break? And when you started The Postmortal, did you know it was going to get published? Did you already have a deal? Or did you put all that effort into this just hoping it might work out? That seems like a big risk for a man to take. Do you remember writing the very first few sentences, what you were thinking and feeling then?

I write at regular hours during the day, like a normal workday. For all my blogging and magazine responsibilities, I work from 9 to 4:30 every day, only stopping to eat lunch or hit the gym. If I have to write at night to finish something I will, but I hate doing it. I’m not the kind of guy who sits there until 4AM working on some idea, and I never will be. I was the guy at the ad agency who would gleefully endorse any idea at 2AM just so we could go the fuck home. I’d much rather watch TV and enjoy myself at night. 

For The Postmortal, I had more time during the day because I wasn’t blogging for NBC just yet, so I was able to write the bulk of it during working hours, with the occasional night session. It wasn’t football season yet either, so KSK and Deadspin weren’t quite as nuts. Once I started working at NBC though, I had to rewrite and edit the book at night. But I never worked past 10PM or anything. I only have so much creative energy in the day. After that, I’m done.

I didn’t have a publishing deal before writing the novel. It was written and rewritten all on spec. Eighteen editors passed on it before Penguin finally took mercy on it and gave it a home. The novel was too long when it was submitted, and the format was different. The dialogue was in this weird screenplay format, which I thought was cool but turned out to be a huge turnoff. (It’s since been reformatted more like a traditional novel, and it’s better for it.) And that happens to me a lot. I’m the kind of guy who writes something the first time and I’m like IT’S PERFECT! Then someone points out something wrong and I’m like FUCK YOU! Then I go back and look and I’m like, “Oh wow, that is wrong. Can’t believe I thought that was right! I sure am a lazy prick!” And I am. 

I remember writing the first part of the book early that summer in 2009, and that first part hasn’t changed radically in the editing process. I had thought about the main idea for weeks and weeks and that scene was more or less complete in my brain before I went and laid it out. And that’s usually when I know I’ve done an okay job: If I’ve written in my head and the actual writing part is just the manual typing.

4. On Kissing Suzy Kolber and Deadspin, you’ve made a solid claim on boasting sports writing’s most profane voice since Dan Jenkins. The Postmortal is relatively scrubbed by comparison (although there’s some balling sex in it). I would like you to write about the use of profanity in modern writing, most especially the use of the word “fuck”—your use of it in particular—as a noun, verb, adjective, adverb, past participle, and form of punctuation.

I use it because it’s how I talk. It just sounds natural to me. And I think profane things tend to be funnier. I’m just wired that way. I gravitated to dirty comics when I was a kid, and that guttural style of comedy stayed me with me. It feels more honest to me when stuff has swear words in it, even though I know that’s mostly an illusion.  But I’m extremely gullible like that. I use profanity and I write in all caps and I know both those things are generally hallmarks of idiocy. But if it feels natural to me, and if it feels like, “This is the best way for my brain to talk to your brain,” then that’s what I do. When it comes to blog posts and stuff, it should feel like you’re having a conversation drunk at 3AM with your friend. It shouldn’t be buttoned up. The book is different because it can’t feel as loose. If you’re gonna stick with me for 360 pages, you need to know that I’m not fucking around.

I’ll give you an example. Ever get a formally addressed email from someone? Like someone sends you an email and it says “Dear Chris,” before the person gets into it? That’s weird, right? That makes me feel incredibly awkward. I try and do everything I can to get rid of any of that kind of formality in blogging.

5. Your writing feels honest. When you write about yourself—such as your account of your lonely college years—you are unsparing. I’d like you to be extra-honest here. The Postmortal doesn’t come out until August. You’ve done the work; now you’re caught in the waiting—in the dreams and nightmares period. What are your hopes for your book? When you spend that much time and exert that much effort on something, is there really any way for the end to meet your expectations? Are you worried at all that your fans might not take to your more… literary… aspirations? Do you care what they think? Was writing a novel something that just had to happen for you? Are you now where you always saw yourself?

Shit man, that’s like eight questions in one. Like the oral exam in Back to School. [Ed. note: Sorry, dude. Five questions is really hard for me.] My obvious hope for the book is that it sells 100 million copies, makes me a multimillionaire, wins the Pulitzer and the Nobel, gets turned into a Best Picture-winning film, and gets turned into a TV series and I have a taste of the syndication fees. 

But this book nearly died on the vine a couple of times, the first time when my first agent said she didn’t care for it, and the second time when all those editors passed on it. So there was a time when I didn’t think it would be published at all. And now it IS being published, and then it got picked up by all these foreign countries, and people seem to like it. So it’s kind of been reborn in my mind. It’s been an extremely rewarding process, even though it can be maddening at times. (Like, sometimes a copy editor will add a comma or something and it will completely throw me off and cause me to question the whole fucking thing.) I read Frank Bruni’s book and in that book Frank goes on a camping trip and wants to quit and the counselor is like, “There are things you enjoy doing, and things you enjoy having done. The latter is better.” Well, this sure as shit goes in the latter category. Also, camping blows.

When I did the first book, I didn’t know how the process worked and so I got all geeked up for the release date when that’s really kind of a letdown. By then, everyone you know has read the book, and everyone who’s going to buy the book isn’t going to read it for days, months, years. So now that I know all that going in, it’s been much more enjoyable to write this and get it out and have people read it and respond well to it. In that way, it’s already been a lot more than I hoped for. But on another level, I want that billion dollars, because I want a Waverunner. Waverunners are the tits.