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Q&A: Bill Simmons (cont.)

Posted: Wednesday March 22, 2006 5:40PM; Updated: Monday March 27, 2006 1:39PM

SI: What's next?

BS: I think this is going to be it for me. I really want to move into scripts next. I'm ready to do it. I've been doing this since '97. At the spring of next year, my contract ends. That would be 10 years. I'm not saying I wouldn't come back. But I think 10 years is a nice run. Maybe keep my NFL column and that's it.


SI: I was wondering what would happen if your audience aged with you. Would you be the 55-year-old Sports Guy, not writing about trips to Vegas but rather about your grandkids?

BS: And that's why we're never going to find out. With the Sports Guy gimmick, having the kid was the beginning of the end. I hit my mid-30s. We're at the end of the line. I don't want to be that 42-year-old guy sitting on a barstool, saying how hot Anna Kournikova is. I never want to be that guy. Maybe it could evolve into something different, not called the Sports Guy.

SI: Did you enjoy your time writing for the Jimmy Kimmel show?

BS: It was great from the standpoint of writing jokes and dealing with people. I loved it. I don't like the hours. I was starting columns at 9 p.m., turning them in at 4 a.m. I loved Jimmy, but I got frustrated at times. He's the boss. If he didn't want to do a joke, it didn't go.

SI: It took a lot of wrangling with the ESPN p.r. people to set up this interview. I was starting to think you were going to pull a JD Salinger on me.

BS: Yeah, sorry. I always get nervous with this stuff because ... I don't know. It's just weird to be written about. It's weird to be written about when I'm a writer. I see it from your side, all the angles. Getting back to the pioneer thing, the thing I'm proud of is I've had a solid career now. I've been at ESPN five years now. I read the old columns now -- they're pretty mediocre. In the spring of '99 I really figured it out. That's a long time. I'm proud of that and I'm proud that it's different from the other stuff.

SI: You talked about inspiring younger kids. Is that necessarily good? Do we want a generation of young writers trying to ape your style?

BS: Hmmm. At the book tour, it was mostly people under the age of 30. A lot of college kids and some high school kids, and it seems like that generation is the one that's going to be really interesting. I do think people take on the habits of what they grow up reading. I grew up reading this Hall of Fame Globe sports section, and I think people who grew up 15 years later, they probably don't feel that way. People who've been online the last four to five years reading, they've been reading people who are really trying to look at different ways to look at things, write from a fan's perspective. It will be interesting to see what the next generation is like, and for me that's always been the thing, that I've kept the fan's perspective. That's been the most important thing

SI: Do you think moving out to Los Angeles and working on a TV show hurt that? You weren't the typical fan anymore by any means.

BS: Absolutely. It was weird because I had always mentioned whoever I was hanging out with. So now I'm hanging out with people, a couple who are celebrities, and sometimes [Adam] Carolla would have great stuff and I'd throw it into the column and they'd be like, "You're name-dropping." And I'm like, "These are my friends. We hang out like five hours a day." Now it's like I can't mention people I'm hanging out with, so that was kind of weird. I'm sure for some people back home, they can't figure out why I'm still out here, and sometimes I can't either.

SI: Have you thought about moving back?

BS: You get occupied by the weather, especially when you're a writer and you're stuck in front of a computer. It's nice to know that it's 80 degrees. And I do want to write scripts and I can't do that from Boston. You have to live in L.A. or New York to do that, and I would never live in New York