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ESPN's Bill Simmons on His Mini-Empire, Why Hollywood 'Sucks' and Why He Won't Write about Sandusky (Q&A)

This article first appeared in the Dec. 2 issue of The Hollywood Reporter magazine.

I don't care what anybody says, I'm not afraid to try shit," says Bill Simmons, reclining at his desk in his sparsely decorated downtown Los Angeles office. In this case, Simmons, 42, whose wit, humor and often irreverent Sports Guy column have turned him into the most prominent sportswriter in the country, is referring to Grantland, the ESPN-backed site he launched in June.

By September, the site -- a mix of intellectuals pontificating on the entertainment triumvirate of sports, pop culture and Hollywood -- was luring 2.4 million unique visitors a month, according to ComScore. It's quite an addition to the Boston native and former AOL blogger's portfolio, which boasts two best-selling books, the Peabody-winning 30 for 30 documentary series, 1.5 million Twitter followers and a collection of B.S. Report podcasts that are each downloaded about 750,000 times.

The married father of two, who moved to Los Angeles to write for Jimmy Kimmel Live! and maintains legions of Hollywood fans who appreciate his ability to compare a game to an episode of The Wire (these days, he's even recapping TV shows), sat down to discuss his vision for Grantland, his Hollywood gripes and his tentative plan to add "TV star" to his résumé.

The Hollywood Reporter: Why did you decide to do Grantland?

Bill Simmons: I had spent three years working on this book, and I was hitting 40, and I was like, "What do I want to do long-term?" I always wanted to create a site that was sports and pop culture. 30 for 30 had a big impact because I loved how that was about finding, empowering and working with these incredible directors, and I thought the same thing could work for writers. I researched different sites and looked through all of my favorite magazines and tried to find people who were on their way up.

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THR: How did you convince ESPN to fund it?

Simmons: Simple -- I would have done it with somebody else. My contract still had 10 months to go, and we started talking about it, and I said: "I want to figure this out, and I want to do it here. But once we get to the end of those 10 months, I'm still going to do it."

THR: Podcasts are a big focus for you. Is there a real business there?

Simmons: Yes. I think we can cut them into TV shows, and I think ESPN and ESPN 2 can run them. That's why we built the studio to do half-hour shows or hourlong shows or whatever.

THR: So you're planning to turn your podcast interviews into half-hour sit-down interview shows?

Simmons: Yeah. If you look at the ESPN schedule, there are a lot of times where, say, a Game 7 fell through, or they thought a game was going to happen and it doesn't. Or right now, where they thought they'd have all of these NBA games that they don't have. They have time, and if you have evergreen content you can give them, they're going to run it if it's good.

THR: As far as guests go, who's on the wish list?

Simmons: I think the best podcasts we've done have been ones where people are smart. I did a podcast with Ticketmaster CEO [Nathan Hubbard], which I thought was great. I'd love to have Aaron Sorkin on. Larry David would be really fun. Anybody who has created a great show -- David Simon or Matthew Weiner. I can always get commissioners and sports people, but I'd like to dive into Hollywood a little more. I'm approaching it a little differently. I think when they do industry interviews, it's always "inside baseball." This is going to be a good conversation.

THR: What else do you want to do with Grantland that you haven't yet?

Simmons: We talk about it as though there are TV seasons. Season one, which we just finished, was about not going down in flames, building an audience and hiring a full staff, which we didn't have until Labor Day. We have four more hires to make, then we'll be done at about 16 total. Season two is continuing to get writers. One of the things that I was hoping would happen right away was getting celebrities to write for us. Any time a celebrity who can actually write wants to write something, they do it for the Huffington Post, which pisses me off.

THR: In May, before Grantland launched, you said in an interview that you weren't sure you'd create the site if you had to do it over again. Still feel that way?

Simmons: It was probably the worst possible time for me to have done an interview. We were launching in four weeks, and we weren't ready, and I could potentially go down in flames. Look, we launched before we should have, and we didn't have enough people. We also had people watching us and were hypercritical the first few weeks -- which I didn't think was totally fair, but I get it. The same thing happened when we launched Jimmy's show. You get judged by your first week when you should get judged by your 30th week. Jimmy's show didn't even start to become the show that it is now until 18 months in. He can say all he wants, but he's full of shit. (Laughs.) You learn, and you make mistakes. It just seems like people are afraid to try things.
 

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THR: Will you do another 30 for 30 series where you commission Hollywood directors to make documentaries about sports stories, people and events?

Simmons: Oh yeah, we're planning it. I don't know if it'll be 30 or 35 docs, but I'm pretty confident it's going to happen. It was so hard to get 30 last time, and the series probably hit about 70 percent of its potential. We were learning as we did it. As we explained it to directors, we could see their wheels turning, like, "Yeah, that sounds great." Then you could tell they were thinking, "I'm not f--ing doing this for ESPN." This time around is different, and I think [ESPN's] Connor [Schell] and I will be able to get whomever we want.

THR: What else haven't you done that you'd like to do? A feature documentary?

Simmons: I want to do one. I can't talk about it, but I've got one idea that I think will be really good. And ESPN really wants me to do TV. They want me to do an NBA show, which now it doesn't matter because the season is getting canceled.

THR: What would your NBA show look like?

Simmons: That's part of what we're trying to figure out. I wouldn't do it the typical way that we do it. For me, it would have to be more loose and Morning Joe-ish because I'm not a real TV person, and I would never want to be one of those guys that stares into the camera. I've never been good at it, either.

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THR: How about selling a sitcom? ABC is developing a Boston sports-fan sitcom; what about a Boston sports-guy comedy?

Simmons: I definitely wouldn't do that. I had a couple of experiences with TV and movies, and it just sucks. There's so much that you can't control, and there are so many different ways it can get f--ed up. You might have a show and they hired a shitty showrunner and the show sucked, or you might have some network executive who after you've got through the whole process just decides he doesn't like your lead or he doesn't like your pilot. I sold two shows, and each time they went nowhere.

THR: What is the most underexploited sport on TV?

Simmons: Hockey. It was a real shame that it didn't work out with ESPN. It's a great spectator sport, and it looks great on TV. They've fixed a lot of what was wrong with it, and I think this window that they have with the NBA stupidly imploding could be a really great thing for hockey. But it's on Versus.

THR: How would you improve baseball coverage, which has struggled in the ratings?

Simmons: They have to speed the game up. You'll have these great games every once in a while that make everybody think you don't need to do that. But it's skewing old. I look at my son -- he has to be doing three things at once at all times, and he's not going to sit there for nine innings. It's just not going to happen.
 

Bill Simmons Sounds Off...

NFL IN Los Angeles: I think the stadium belongs downtown, I think it's going to happen, and I'm already preparing emotionally for the day when my son tells me, "I know you root for the Patriots, but I want to root for L.A.'s new team like the rest of my friends." And then I tell him: "Pack your things. You have 10 minutes to get out of my house."

Fate of the Dodgers: It's the best deal in sports: an iconic brand, great fans, a famous stadium and tons of land. Someone smart will buy them and do what the Red Sox owners did -- cut deals with restaurants and bars, build around the stadium and make it more fun to go there. Plus, you'd be an instant hero with Dodgers fans. Following the McCourts is like following a boyfriend who's hung like a mouse -- you can't lose.

NBA Lockout: The owners wanted to blow up the season; the players gave them gas and matches. They deserve each other. I think we're going to lose the entire season. But, hey, any time you can shut things down after one of the five greatest seasons in the history of the league, you have to do it.

Penn State Scandal: It continues to horrify and disturb. As a parent, I just find myself unfathomably disappointed by everything about this story, to the point that I can't even write a column about it. I have no take. I don't think I could hand in, "I'm dejected and angry," as an entire column.