Chatting with Grantland's Andy Greenwald

ESPN’s pop culture and sports guru extraordinaire, Bill Simmons, realized a major goal this past year with the creation of Grantland. As Grantland has gotten its feet underneath them, it has started to churn out a daily offering of commentary on sports, television, movies, and everything in between in the world of entertainment. The site serves as a stable for young, talented and handpicked writers who fit the sensibilities of a typical Simmons’ reader. One of the Grantland writers who have emerged as one of the best is Andy Greenwald.

Greenwald grew up in Philadelphia and attended Brown University. Although he is just 34, he has already compiled an impressive writing resume. In addition to authoring several books, he has also written for mainstream publications like Spin, Entertainment Weekly, and the Washington Post.

I first came to appreciate Greenwald’s work at Grantland because of his analysis of television shows such as The Walking Dead and Homeland, which was just as entertaining as the dramas themselves. In fact, I never would have sought out Homeland if it wasn’t for reading one of Greenwald’s articles, which led to me watching the entire first season and realizing it was one of the best shows on television this past year.

While Greenwald mainly writes about entertainment subjects for Grantland, he is a longtime baseball fan, rooting for his hometown Phillies, so he is a perfect fit for the site. I must admit that he makes me totally envious because I want his job. Despite my jealousy, it is not mean spirited, and how could it be with Greenwald being such a nice guy? It was pleasantly surprising to find such a busy writer so accessible and willing to answer my questions. The result is this interview where Greenwald shares more about his background and his insights on writing.

Andy Greenwald Interview:

How did you first become interested in writing?: Not sure if there’s an easy answer to this question! I think all writers begin as readers and that’s certainly how I spent a worrying amount of my childhood. By the time I was in college, I had gravitated towards writing in all forms: creative, academic, and, more than anything else, telling people my opinions about records and bands.

What has led you to write about the topics you do (social commentary, music, TV, baseball, etc...)?: I think the best writing comes from passion and those are certainly subjects I feel strongly about. When I was younger, music was not only a primary interest it was also the one topic a novice could plausibly write about professionally without a single shred of expertise. Over time, I’ve turned away from music and more towards television. I realized that, while I love listening to music, I no longer have much interest in how that particular sausage is made. Call me jaded, but, twelve years on, the insights of 22-year-old drummers don’t hold the same allure. In contrast, the business and art of storytelling fascinates me, especially as I endeavor to do my own writing for the small screen.

The baseball writing is really just cheaper than therapy. The bills can add up as a Phillies fan, despite the success of the last few years.

How did you come to write for Grantland?: I feel extremely fortunate about how it all worked out. I knew about the site well before it was announced because a number of friends of mine, including Chris Ryan and Chuck Klosterman, were involved. But it wasn’t until April when Lane Brown, my former editor at New York Magazine’s Vulture blog, got in touch and asked me if I’d be interested in coming aboard as a contributor.

With the marked decline of print media, where do you see the future of writing heading?: I’m not sure I’m qualified to opine on the future of writing. The rise of the web has certainly provided a venue for more writing than the world has ever seen. Good writing, though, and writing that is well-compensated ... those are still in flux. My experience with Grantland has, however, restored my faith in the notion that it’s possible to find outlets that treat writers with respect and can attract an opinionated audience willing to read – and wildly disagree with! – longer-form pieces.

How much of a baseball fan are you? What is your background with the game?: I’m a dangerous baseball fan as I’m both wildly obsessive and painfully sensitive. During the season I live and die with every pitch – and that’s even when my team is forty games above .500.

I grew up conditioned either to love or loathe the game as my father is a die-hard St. Louis Cardinals fan (despite hailing from Pennsylvania); the soundtrack of my childhood was the voice of Jack Buck occasionally breaking through the oppressive static of KMOX as my dad desperately tried to tune in from the east coast. By the time Joe Carter broke my heart into a billion pieces in 1993 I was a scarred Phillies fan for life. Is it time for pitchers and catchers to report yet?

Do you think baseball (and all sports) can benefit from the more honest approach Grantland takes to writing?: In general, I think all writing can benefit from an honest approach; dishonesty tends to leave an unpleasant aftertaste whether you encounter it on the sports page or on an episode of your favorite TV show.

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