When Bill Simmons first became the Boston Sports Guy, writing an obscure blog for AOL in the early days of the internets, he gradually cultivated a loyal audience who appreciated his exhaustive essays dissecting Beantown’s sport fandom while sprinkling in Karate Kid and Road House references. He wrote from a fan’s perspective, which is the only perspective he could afford at the time, but that voice ultimately made him famous and influential. He’s been at ESPN now since 2001, and if he doesn’t yet run the network, he certainly is one of the Sports Leaders’ most important assets. In addition to being the editor in chief of Grantland.com, he also is an executive producer of their heralded 30 for 30 documentary film series, the host of the popular B.S. Report podcast, and an occasional guest on Pardon the Interruption.
Beginning tonight, he’ll also be taking a seat next to Magic Johnson, Jalen Rose, and Michael Wilbon as a contributor on the KIA NBA Countdown show, ABC/ESPN’s basketball showcase studio show. The one-time outsider is now the ultimate basketball insider. It didn’t happen overnight or by accident. The best-selling author of The Book of Basketball spoke to EW about conquering the business from the outside-in, why he said no to the show last year, and a hilarious Godfather-like offer he once received from one Mike Francesa.
ENTERTAINMENT WEEKLY: With NBA Countdown, you are now officially crowned an “insider,” if that wasn’t already clearly established before. How does that impact the way you think about sports and the way you report on them?
BILL SIMMONS: I try not to think of it as a negative. I definitely am in contact with a lot of people now, and I’ve tried to get information that helps me understand sports better and helps the narratives of the things that I’m writing without making it seem like I’m too “inside.” I think there is a balance. People will be looking for stuff that is from my perspective, but TV’s going to be interesting. I’m always worried that there’s going to be some terrible Celtics playoff loss or something and then I have to go on TV two minutes later. What will my state of mind be like? I don’t know. And I don’t know if anybody who’s been on TV on one of these major studio shows has ever really been in that position before. I’d like to think I can handle it professionally, but who knows? I don’t know how it’s going to play out.
In the early days of your column, it was easier to say anything about anybody without any repercussions, in the sense that you were just a fan. As you say, though, you know some of these athletes now. Is it difficult to maintain the same objectivity?
In Almost Famous, Lester Bangs tells William just to be honest and unmerciful. I always thought that was a good lesson for this because I don’t think it helps anybody if I’m pulling punches. On the other hand, you don’t want to do that thing where you’re, Look how honest I am! And you’re just throwing crazy stuff out and hoping some of it hits. I’ve written a lot of stuff and I’m going to continue to write during the season, and the honesty of whatever I’m talking about has to have the same spirit as what was in the columns. And I definitely will not hold back. The one thing you do have to be careful of is if you’re going to criticize somebody, you just have to know that it’s going to be condensed into 140-character tweets and sent out as “Simmons said X about X.” And that stuff is going to end up in the person’s timeline and they’re going to see it. I just think that has to be in the back of your mind.
You’ve gradually been moving towards this for years, and your appearances on PTI must’ve surely given you confidence that this was something you could do well.
The more you do it, you eventually realize, What’s the big deal? There’s two cameras pointing at you and there’s a bunch of people standing there, but ultimately you’re just talking about sports. The art of doing TV is to be able to roll with the punches when stuff goes in a different direction. That’s when you’re getting good at it. That’s the stuff I’ve been trying to work on. Concentrate on ad libbing and playing off people and making a joke when you can.
You’re not the first writer to make this kind of leap. In fact’s PTI’s Tony Kornheiser had a brief stint on Monday Night Football. Has he offered any advice to you?
I talk to Tony a lot. He’s an honorary uncle, and we’re kindred spirits because neither of us can shut up. But I think Tony on Monday Night Football was a little bit of a different situation. You’re watching a football game, and there’s a certain level of expectation for the people you’re listening to. You just want to feel like they played or they coached. It was the same problem Dennis Miller had. Every time someone talked who wasn’t the player or the coach, you’re kind of like, Well why is that guy telling me about the blitz right now? He couldn’t win. That was a no-win situation. I feel like he actually did as well as he possibly could’ve done in that spot. For me in the studio show, it’s a much easier way to succeed because there’s no game. I’m not interrupting you during a game.
I’m guessing tonight won’t be the first time they throw the four of you together to talk hoops. What’s been the learning curve?
No. It’ll be the second time. Much to my chagrin, we didn’t have a lot of rehearsal. We basically went on and did our preseason double-header last week. That was basically a live rehearsal. I think it will be one of those things where it take six weeks to figure out very subtle stuff that you just wouldn’t know unless you were doing it: When can you jump in where someone is finishing their sentence? There’s a real art to that. You need a certain rhythm and you need a certain history between the four guys, and that takes a few weeks. The other thing is, what roles do you fill? That’s something I don’t think people put enough thought into with television shows. You see every network do it; they’ll just hire people because they’re names. And they put no real thought into how those people will mesh. That’s why I thought it was so important for us to get Jalen as the fourth guy for our show. We have me and Wilbon who can drive the show from an opinion and information standpoint, and then we have Magic who is like the NBA buddha. He’s been in every conceivable situation and just understands everything that’s going on better than any of us ever could. And then you have Jalen, who played for a long time and has played against most of the guys that we’re watching right now. So I think we have a really nice blend of opinion and experience.