The Fury Files: Will Leitch

Welcome to the latest edition of the Fury Files, the favorite Q&A of people who think the world really is ending on December 21. Check out previous editions with Tom Linnemann, John Millea, David Brauer, Joe Posnanski, Pat Coleman, Kevin Van Valkenburg, Michael Kruse, Chris Jones, Chris Ballard and Roland Lazenby.

This week’s guest is writer Will Leitch. I’d put a magazine or website name in front of writer, but Leitch works for such a wide variety of publications, it’d be impossible to put just one title there. Leitch is a contributing editor at New York Magazine, where he usually writes about sports but displays his versatility on a regular basis, like when he interviewed Spike Lee. Earlier this year he became a contributing writer for the new website Sports on Earth, a fun site that includes contributions from writers like Joe Posnanski, Chuck Culpeppper and Gwen Knapp. There he writes about a variety of topics. A defense of Joe Buck? A story on the Nets-Knicks game? A piece on the beleaguered Arizona Cardinals? They’re all on Sports on Earth.

Leitch is a regular contributor to GQ, where he’s written in-depth profiles of Michael Vick, Derrick Rose and Jeremy Lin. It’s not all about sports, though. With longtime friend Tim Grierson, Leitch regularly reviews movies for Deadspin. Leitch is the founding editor of the Gawker empire’s sports site, which he left for New York magazine in 2008.

A native of Mattoon, Illinois, Leitch is a passionate fan of the St. Louis Cardinals baseball team and the Arizona Cardinals football team, who earned his undying loyalty when they were losing games in bewildering fashion in the Midwest instead of the Southwest. Leitch graduated from the University of Illinois and is still in love with the football teams and basketball teams. He might still have a Kenny Battle poster hanging in his bedroom and at some point in his career — either for Slate or a weekly paper in Illinois — he’s likely written 3,500 words about why Jack Trudeau to David Williams was the most underrated quarterback-receiver combo in NCAA history.

His enthusiasm for his favorite sports — for the players, the teams, the games, the moments — remains one of his greatest strength as a writer, but he’s also great at writing. And he can handle it any form, from long magazine profiles to short opinion pieces on the web. In addition to all of his other work, Leitch is the author of four books, including his most recent, Are We Winning? Fathers and Sons in the New Golden Age of Baseball. If you need more of his writing? There’s always his Tumblr page. Or Twitter.

Here, Leitch talks about Spike Lee and Woody Allen, the 1987 World Series (Twins!), Letterman, the difference between magazines, websites and books, what motivates him as a writer and a lot more. Thanks a lot for your time, Will.

You’ve been at New York magazine longer than you were at Deadspin. But most people probably still think of you primarily as Will Leitch from Deadspin, and in a decade that will probably still be the case. As much pride as you have in creating the site, does that ever annoy you or have you accepted it’s probably always going to be in the first paragraph of your biography?
I’m proud of the work I did at Deadspin, and certainly having my name associated with them now, when they’re consistently doing much more ambitious, intelligent work than I ever imagined from the site, is something I don’t mind at all. But you never want to be known primarily for something you did years ago either. I work even harder now than I did then. Though we shouldn’t overstate the association: The vast majority of comments I get on my movie reviews there are, “Who the hell is this guy?” People on the Internet have short memories.

The Spike Lee interview was one of my favorite pieces in New York magazine this year. At what point did you decide to run it in that format, with the complete Q&A, instead of interviewing him and then turning it into a feature? Does running the interview in that manner provide advantages you wouldn’t get in a normal profile or was there something specific about profiling Lee that led to the decision? And when you go in for those sit-downs, how closely do you follow prepared questions and how much do you improvise, which can provide some fun sparring?
Well, that’s a regular format for those sort of interviews in the mag: They also did one with Tina Brown, and Aaron Sorkin, and Barney Frank. I think the Spike Lee one came out so well because, well, I know Spike Lee’s work really well. He was one of the first filmmakers I really got obsessed with, so I’ve seen everything he’s done, the good and the bad. So I was fortunate to be in a situation where I had a million questions, informed questions, I wanted to ask him, and a full two-and-a-half hours to ask them. Plus, he’s such a combative, intelligent person that the back-and-forth – me realizing he’s willing to fight me, him realizing that I actually know what I’m talking about – couldn’t help but be entertaining. That might be my favorite piece I’ve done for the magazine, to be honest.

You’re 12 years old and watching the 1987 World Series in Mattoon, cheering for the Cardinals. I’m 12 years old and watching the Series in Janesville, Minnesota, cheering for the Twins and throwing darts at a Whitey Herzog baseball card my friend pinned to the dartboard in our basement. To me, that title remains the most exciting sports moment in Minnesota history, even more special than the greatest World Series ever four years later. Thunderdome, first Twins title, Hrbek’s slam, Berenguer Boogie, Homer Hankies. But where does that Cardinals team rank in the memory bank for St. Louis fans? It wasn’t a title and there was no Denkinger-like catastrophe. It was just an inferior team winning a series because of baseball’s bizarre way of choosing homefield advantage. And it was the last time the Cards made the playoffs until 1996. It was Whitey’s last great team. What stands out about that team, that season and that World Series?
All I remember is the noise. The idea that everybody has to shut the hell up when Tiger Woods is trying to drop a three-foot putt but Willie McGee has to hit a Juan Berenguer 95-mph fastball with all that madness going on is insane, and perverse. That said: We weren’t nearly as angry about that World Series loss as we were about 1985. Every Cardinals fan who remembers that 1985 team considers them their favorite. That World Series was OURS. I love that when Jon Hamm, a diehard Cardinals fan, plays celebrity softball games, he wears a “DENKINGER 85” jersey. There’s nothing like that from the ’87 Series.

David Letterman was a huge influence on Leitch growing up.

Worldwide Pants names you executive producer for Letterman’s show for one night. How do you format the show? Shorter Late Night monologue or longer Late Show monologue? What studio bits do use or do you send Dave out for a classic remote piece? Who’s the first guest, second guest and musical act? And, somewhat creepily, you can select any Letterman between 1982-2012 to host the show? Which Dave do you select?
I’d go shorter monologue, but then again, I’d probably get the show canceled that way. People like monologues, even if Letterman clearly dislikes them. I’d LOVE to see him go out with Siskel & Ebert, for an obvious number of reasons. I’ve always wanted to see him interview Woody Allen: I wonder if they’d see each other for the kindred spirits I’ve always seen them as. But honestly: I love the Dave of right now. He’s more relaxed, and more comfortable with his power. I know everyone says that he was best in the ’80s and that he’s past his prime, but those people are wrong. His most underrated skill has always been his interviewing: He’s the only one of the guys who can really care, and that makes all the difference.

What New York sports event leaves you the most excited when thinking about the next day’s backpages in the Post and Daily News? A close Yankees playoff defeat? A defeat of the French in some major international competition? A Mets collapse (when they were at least in position to collapse)? A Jets controversy? A Madison Square Garden disaster?
I actually sort of hate the backpages of NYC papers when something bad happens. I’ve lived in New York for 13 years, and I’ve still never gotten accustomed to that sort of negativity. I guess I sorta never want to.

Even though your byline pops up everywhere, I was still somewhat surprised to see it in Parade magazine earlier this year. How did that feature come about? And say your name can appear in one other spot in Parade, are you asking a celebrity question of “Walter Scott” or a brain-teaser to Marilyn vos Savant? And what’s your question?
Oh, they were just looking for a sports story and knew I’d be able to turn it around very fast. It was the first piece of mine my grandmother ever read, so that was nice. And I will neither confirm nor deny any canoodling rumors involving me and Ms. Vos Savant.

Leitch has been at New York  since 2008.

New York magazine, GQ, nonfiction books, a novel, New York Times, glogs (R.I.P glogs), Parade, Deadspin, Yahoo, Tumblr, more. From a pure writing perspective, which format do you enjoy the most? And what is it like writing for such a variety of publications from the editing side? What’s the editor-writer relationship like in the magazines compared to writing a book? Or do you prefer having more independence, which I’m guessing you had when you were writing 76 items a day for Deadspin.
You know, I’ve got pretty much the same freedom now that I did at Deadspin. I do have better editors, and that makes all the difference in the world. To get to write for New York magazine is a serious, sort of amazing privilege. That is the best group of editors in the world. Everything they touch is improved; it’s like everything goes through a genius blender. It is my favorite magazine and I still can’t believe I get to work there. Hell, I wish they could edit these answers.

You’ve lived in the Midwest, Los Angeles and New York. Does geography play any role in how you perform as a writer? Does being in the media capital influence your interests or style? Would living in perfect weather make you a different writer? Do editors have any preconceived ideas about writers based on where they live? Does being in the Midwest…I don’t know, somehow quiet your voice? Or would this question make much more sense before something called the Internet was invented?
It might have 10 years ago, but now, honestly, it’s all just work. It took me a long time to figure out that it’s really all just about sitting in a room and typing your ass off and not worrying about anything else. I think I used to “play” a writer more than actually be one. To be a writer, you have to write all the time. It’s the only way to get better, and it’s the only way to, you know, make a living. So that’s what I do. I’d do it the same way if I lived somewhere else, though my rent would be a lot cheaper.

In an interview with Gelf in January 2008 — where you also called Obama’s victory in the election — you said your next book was a “novel about a kid who wants to kill himself on the anniversary of Kurt Cobain’s suicide. I’m WAY behind on it and feel guilty even mentioning it.” I, too, feel a bit guilty mentioning it if it’s something you’ve moved on from or if you’re still paying back the advance, but…what’s the latest with that book?
I’ve moved on from it. I never quite figured out how to connect how a teenager listens to music today and how they did when I was a teenager. I knew if I couldn’t figure that out, the book wouldn’t work. So I bailed. Still have about 100 pages of it somewhere, though. Maybe I’ll bust it back out someday.

How do you approach your movie reviews? Do you want them to influence someone’s decision about whether or not they see it? Or are you more analyzing it for what it is, breaking it down, pointing out the good and the bad and dissecting the art?
I’m just trying to give a fair, idealized-audience portrait of whether the movie works or not. I try not to over-intellectualize it. It’s less influencing someone to see it than hoping people get accustomed to my taste, and where I’m coming from in those, to take what they need from that. I might disagree with Roger Ebert about a movie, but I know his writing so well now that I know where he’s coming from. That’s all any writer can hope for. Writing about movies might be my favorite thing to do, though I’m not sure I’m all that good at it yet. Sure is fun, though.

Your introduction to Cardinals baseball is a classic father-son moment and millions understand how that spawned the lifetime of fandom that followed. But what was it about your introduction to Woody Allen that spawned the lifetime of fandom that followed? You’ve written about renting every Allen movie before leaving for college and watching it with buddies and, since 1992’s Husbands and Wives, seeing all of his movies in the theater. Did the fascination start with Husbands and Wives or had you seen his movies on TV or rented them before that? And since 1992 was also when his personal life imploded, did the scandal register with you at that time or ever affect how you viewed Allen as a filmmaker?
Yeah, I had the misfortune of discovering Woody Allen the very year his life fell apart, which has sort of put me in a defensive crouch when discussing him ever since. That said, caring about who an artist is as a person seems to defeat the very purpose of liking art in the first place, though it’s understandable human nature that we do it anyway. (Also: He’s been with Soon-Yi for more than 20 years now. People still think she’s a teenage girl or something. She’s a middle-aged woman.)

But the movie that did it was actually Play It Again, Sam. His character in that movie, the genesis of The Woody Allen Character, is extremely appealing for nerdy kids trying to get girls but not sure how.

Choose a writer for these stories/projects:
* A thousand-word column after Jeremy Lin scores 45 points — in front of a frowning James Dolan in the front row – in a 108-90 Rockets victory at Madison Square Garden.
Hua Hsu.

* A 5,000-word (give or take) magazine feature on Vin Scully’s final game as a Dodgers announcer.
Pat Jordan.

* A piece after the Vikings lose the Super Bowl 33-31 when Tom Brady hits Rob Gronkowski with a 25-yard touchdown on the final play of the game. (Non-Magary Division).
Someone who violently dislikes Drew Magary.

* A book in the vein of The Franchise, The Kingdom and the Power, It Wasn’t Pretty Folks, but Didn’t We Have Fun? or any of the other hundred books like those I have in boxes or books. But this one will be a history of Gawker Media. Maybe it’s not written for 10 or 15 years, but a thorough biography of the company.
I’d want to go big on this one. Make Lawrence Wright do it. Or, in lieu of that, just assign it to Felix Salmon.

A lot of people read Leitch’s 2010 book Are We Winning? But did dad Leitch?

Going back to your Life as a Loser columns, you’ve never had a problem being brutally honest about yourself in your writing. And you’ve always written about family. But did you struggle with the idea of writing extensively and honestly about your dad and your guys’ relationship in “Are We Winning?” Did having it in a book, which somehow makes things seem more permanent, add pressure? And did he ever read it or deliver a review?
My dad was the only person I didn’t want reading that book. My mom claims he has, but I have no proof and will hear no evidence to that end. Tommy Craggs once was on a plane with my dad and texted me to say that Dad was carrying a copy of the book. I asked him to slap it out of his hand.

Honestly, having written about my life for so long in “Life As A Loser,” and doing it at such a young age, has inspired me to try to do as little of it as possible now that I’m a grown-up.

The feature on you in the Illinois Alumni magazine ends with your quote, “I try to say yes to everything, because I’m sure that in two years it could all end.” In some ways it’s a classic writer’s quote, that insecurity or feeling that someday someone’s going to say, “You’re done, go back to the farm in Illinois.” But at the same time… realistically, it’s probably not going to be a problem for you. At this stage in your life as an established writer, what drives you? Taking on different types of stories or projects? Memories of being the Inwood resident who had $1.74 and walked 190 blocks home one night and being determined to never be in that situation again? Or is it just doing the best job you can, day in, day out, the writing equivalent of your dad going to work each day as an electrician?
I’m glad you feel that way, but I sure don’t. This isn’t a stable career by any stretch of the imagination. I work for a weekly magazine, for crying out loud. Mind you, it’s a terrific, profitable one, but this industry changes so quickly that no one should ever feel comfortable anywhere, doing anything. I feel like I always just have to be a couple of steps ahead of the coroner. I figure if I type really fast, if I always turn in everything in time, if I keep doing things that I enjoy doing (and therefore make sure this never gets stale for me or the reader) … maybe I’ve got a chance. But I spent a long, long time writing thousands of words that nobody paid me for, that nobody read. Once you’ve had a taste of that, you never forget it. If you want to tell me, “You’ll always feel that way,” then that’s good: That means I’ll always be worried rather than, you know, starving because it all went away. Forget not taking it for granted forever: I just want to make it to next year.

That’s what makes it fun, right? I hope?