The Sports Guy goes Hollywood: Can Bill Simmons make Grantland a must read for pop culture lovers?

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Bill Simmons is best known as ESPN’s crazy, shoot-from-the-lip Sports Guy whose eloquent waxings — about his beloved Boston Celtics, ludicrous Super Bowl hype and, above all, why Kobe Bryant is a spoiled rotten scoundrel — have made him arguably the most-read sportswriter in America. But now Simmons is moving into new territory launching Grantland, a website showcasing his geek love — and sharp tongue — not just for sports but for movies, music, TV sitcoms and other pop culture artifacts.

Bankrolled by ESPN and up since early June, the website takes its name from the sainted early 20th century sportswriter Grantland Rice, whose famous epigram (“For when the One Great Scorer comes to mark against your name, He writes — not that you won or lost — but how you played the Game”) runs across the top of the home page. The Rice maxim is an unusual choice since Rice was a hero worshiper, comparing the sports figures of his time to Greek gods, while Grantland approaches its subjects with the sort of edgy, hyper-personal attitude that has about as much in common with Grantland Rice as Michael Bay does with D.W. Griffith.

The site’s masthead is adorned with the likes of Chuck Klosterman, Dave Eggers and Malcolm Gladwell, and its stories run long, in keeping with Simmons’ philosophy that it is foolish to chase page views by emphasizing quantity over quality. For me, Grantland is already required reading. Where else could you find a story about the odd-couple relationship between Boston Red Sox Manager Terry Francona and General Manager Theo Epstein right next to a textual analysis of the building-phobia in Christopher Nolan’s thrillers?

There are also plenty of meat-and-potatoes pieces about matters like Shia LaBeouf’s angry young man antics and Colin Farrell’s emergence as a character actor. In keeping with Simmons’ own writing style, which is often punctuated with exhaustive, David Foster Wallace-style footnotes, Grantland often finds a way to apply baseball nerds’ love of sabermetrics to the realm of showbiz.

Lane Brown, for example, dreamed up a system to measure which Hollywood actors have done the most to tarnish their Oscar gravitas, inventing a unit called a Cuba, in homage to Cuba Gooding, the actor who may have fallen the furthest after his brush with Oscar glory. The story is a hoot, skewering the likes of Frances McDormand (for the sin of appearing in “Transformers: Dark of the Moon”) and Christoph Waltz (“The Green Hornet”), with the highest Cuba score going to Natalie Portman, for appearing this year in “Thor” and “Your Highness.” As Brown quips: “New Oscars are always the most easily tarnished — but she might as well have dropped hers in a deep-fryer.”

Simmons, 41, has always been a pop culture junkie. An only child, he grew up on both a steady diet of Boston Globe sports columnists and ‘70s sitcoms. He began writing an online column for ESPN in 2001, which from the start was always loaded with pop culture references and digressions. In his recent Grantland column about the NBA lockout, he managed to get only three graphs in before he was comparing the negotiations to a scene from “Dave.”

“The thing that’s worked for me is that I write a sports column, but I can weave enough pop culture into it so that people who don’t like sports will still read it,” Simmons told me over lunch, taking frequent breaks to tweet news about a freshly edited 4,200-word column about the NBA lockout on his BlackBerry. “I always thought there was a void between the worlds of sports and pop culture that we could fill. They’ve always had to stay in their respective side of the ring, but I never understood why.”

Ask Simmons for his opinion on almost anything and he’ll find a connection between sports and showbiz. When it comes to the NBA lockout, he thinks the players are deluded if they believe they can keep their current 57% share of league income. “Their stance kind of reminds me of the Hollywood writers during their strike,” he says. “They think they have more leverage than they really do. The players get 57% of revenue now — can you really imagine any star getting that on a movie!”

Simmons is all attitude all the time, an approach that hasn’t earned him much love from traditional newspaper columnists and beat writers. My colleague Mark Heisler, who covers the NBA, has repeatedly dinged Simmons, dissing him as a symbol of the modern ESPN media’s “worship of attitude, however unapologetically jingoistic, self-centered and self-congratulatory” it might be.

Simmons makes no apologies, again offering a showbiz analogy. “I’m no fan of the way newspaper sportswriters work, especially when they complain about people like me not going into the locker room,” he says. “All they do is point their mikes at the athletes, trying to hear what they have to say, which is usually nothing. Is that really any different from a Hollywood press junket, where every star gives the same generic answers to the same five questions? It’s gotta be the biggest waste of time ever.”

Simmons’ overriding goal for Grantland is to fashion it into a site that connects the dots between disparate cultures. It bugs him that people may care deeply about the Oscars but in his mind don’t have the same kind of forum for avid debate that sports fans have with sports talk radio, websites like Deadspin and ESPN’s endless array of sportswriter debate programs.

For Simmons, having “The Social Network’s” David Fincher lose the directing Oscar to “The King’s Speech’s” Tom Hooper — whom Simmons breezily dismisses as “a guy who’ll be forgotten in 20 years” — was no less painful than seeing Kobe Bryant making the all-NBA first team over Dwyane Wade. “Wade meant more to his team, just like Fincher meant more to his movie,” he says.

Simmons is even still worked up about the 1994 Oscar race that saw “The Shawshank Redemption” and “Pulp Fiction” lose the best picture award to “Forrest Gump.” “If that had happened in sports, people would still be arguing about it,” he contends. “But with pop culture, it’s in one ear, out the other. It’s our job at Grantland to think about that stuff and have fun with it.”

I’m not sure that what the world needs is more people arguing about the Oscars, which seems to take plenty of oxygen out of the blogosphere as it is. But Grantland is refreshingly cheeky, a quality that should always be valued, especially in this embattled era of journalism. When I confessed to Simmons that I’d even found myself sucked into reading Klosterman’s second-by-second analysis of an especially awful 1979 Led Zeppelin performance of “In the Evening,” he smelled victory.

“That’s our goal — to make people waste their time. And as long as they’re wasting their time on our site, we’re winning.”

--Patrick Goldstein

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