It’s no surprise that hard-core Boston fans love their native-son Sports Guy. But why have millions of readers beyond Beantown made Simmons one of America’s most popular sportswriters? Kevin Hench finds out.
Bill Simmons Touches ‘Em All
Bill Simmons began his professional life as the Boston Sports Guy on his Website in the 1990s. In 2001 he dropped “Boston” from his moniker and jumped to ESPN.com. His column was a runaway success, drawing hordes of avid readers from all over the country.
They came for his endless array of pop-culture references, his frequently laugh-out-loud prose, and his clever coinages. Simmons has laid claim to the Unintentional Comedy Scale (self-explanatory); the Ewing Theory, disseminated by Simmons but credited to his friend Dave Cirilli (which applies to a team that loses its star player but improves — à la the 1999 New York Knicks, who lost Patrick Ewing but went on to the NBA Finals); and the Reggie Cleveland All-Stars (honoring players whose names do not seem to “match” their ethnicities).
They stayed for his encyclopedic knowledge of sports, his sharp insights, and, in some cases, just to bitch about his Boston-centric view of the sports world — or simply to hate on his success. Yes, you can take the Sports Guy out of Boston, but you can’t take Boston out of the Sports Guy (well, unless you count his nickname). Simmons, 36, is a diehard fan, though “diehard” doesn’t seem strong enough: He lives, breathes, and drinks the Red Sox, Patriots, and Celtics — and he wears those allegiances on his sleeve. Thus, his readers will occasionally get a column of, oh, 10,000 words on the Boston Celtics (the current Boston Celtics).
Clearly, though, the majority of Simmons readers are willing to tolerate such diversions. After a brief sojourn as a writer on Jimmy Kimmel Live, he returned to ESPN, resumed his monthly column for the magazine and his almost-daily commentary on ESPN.com, and published his first book, Now I Can Die in Peace. The book recounts Simmons’s lifelong love affair with the Red Sox, and the roller-coaster ride of the team’s 86-years-in-the-making 2004 World Series title. It sold out three printings and became a best-seller.
Our man Kevin Hench recently huddled with the Sports Guy to talk about the Holy Cross grad’s holy trinity: sports, women, and pop culture.
Assuming your wife and daughter will never read this interview, which caused more euphoric delirium: the Red Sox winning the World Series in 2004, or the birth of your daughter the following year?
Simmons: They were strangely similar experiences. In each case, I was stressed the entire time and thinking about every possible thing that could go wrong. And then, when everything turned out okay, I was more relieved and drained than anything. Still, I’m going with having a healthy baby — it’s the single greatest experience you can have in life, other than watching the Joe Namath–Suzy Kolber interview on a continuous loop.
For sheer elation, which was the best: beating the Yankees in Game 7 in Yankee Stadium, sweeping the Cardinals, or Adam Vinatieri’s field goal in Super Bowl XXXVI?
Simmons: Winning the Rams-Pats Super Bowl was the biggest for me only because I was there, and because no Boston team had won a title in 15-plus years. So everyone was bitter and miserable, and wondering if Boston fans were cursed and all that crap. I just don’t think you can top winning a Super Bowl for the first time, as 14-point underdogs. It’s impossible. Plus, the game was played in New Orleans and every Pats fan was a drunken, sobbing mess on Bourbon Street afterward. I still can’t believe what happened, actually. It was like one of those Total Recall dream experiences that Arnold would have ordered.
Do you ever worry you’ll wake up one morning, open the sports section, see that Hugh Millen is quarterbacking the Patriots, and realize the whole Tom Brady thing was a dream?
Simmons: Yes. Every day. My old college roommate, Gene McDonough, said it best: “It’s completely unfathomable how far they have come. It’s the equivalent of waking up 15 years from now and discovering that Bangladesh is a military and economic superpower.”
The Red Sox have suffered some high-profile free-agent defections over the years. Where does Johnny Damon going to the Yankees rank?
Simmons: I think he got somewhat of a bad rap. The Sox obviously didn’t want him back. They low-balled him. At least he seemed a little bummed out about it, unlike that traitor hick [Roger] Clemens. I’d give [Damon] a 4.3. With Clemens being a 10.0, of course.
TheYankees: honorable opponent or Evil Empire?
Simmons: Evil Empire, and then some. I love when they pretend like they’re cutting back every winter, then they casually overspend for another potentially washed-up name in his early thirties. I hate them. I truly hate them.
If you could write George Steinbrenner’s epitaph, what would you carve on his tombstone?
Simmons: The answer to the age-old question: What would happen if you crossed Thurston B. Howell and Judge Smails, and gave them a baseball team in New York?
Your childhood hero, Jim Rice, fell short this year in what may have been his last best shot for the Baseball Hall of Fame. Do you think Rice deserves to be in Cooperstown?
Simmons: My childhood hero was Freddie Lynn!
Fair enough, but Lynn doesn’t have the numbers. Does Rice?
Simmons: I always liked Rice, but there was nothing warm about him. He was completely devoid of charisma. You never played in the backyard pretending to be Jim Rice. I thought he was about two quality seasons short of being a Hall of Famer — he just didn’t age well. He was like the Farrah Fawcett of baseball sluggers: three fantastic years in the late seventies, followed by some good ones, and then he lost it overnight.
How can I convince my friends who aren’t Red Sox fans to read your book, Now I Can Die in Peace?
Simmons: Here’s how: It’s about following a team for your entire life, suffering with them, pretty much giving up, then watching everything turn around in the span of 12 days. The book just happens to be about the Red Sox. Any fan can identify with it. Plus, the footnotes are fun and I get to drop some F-bombs. Kinda like right now in this interview. Fuck, shit, ass.
Who is the one person from your life who would be most surprised that Bill Simmons became a bestselling author?
Simmons: Probably my ninth-grade English teacher, who gave me a 60 one trimester: Mr. Griswold. Part of me wanted to mail him a copy of the book with a note like, “Why don’t you give this a 60, you prick?!” But I actually deserved the 60. I never liked the whole studying thing. It always conflicted with sports and TV.
Have you ever written anything in your column that you regretted?
Simmons: At least once a month. My biggest mistake ever was when I had my old Website. I wrote a tongue-in-cheek column about how they needed to stop playing the National Anthem before games because it was a pain in the ass to stand up, especially if you’re holding beer or food, and nobody really gave a crap about the song anyway. People went bonkers. Fortunately I only had, like, 100 readers at the time. If I wrote that column now, I think I would be exiled from Disney like Bill Maher was.
On a scale of one to ten, with one being the health of the pre-lockout NHL and ten being Magic-Bird in the ‘84 finals, how would you rank the current health of the NBA?
Simmons: Probably a solid seven. The biggest problem is when they have seasons like this one, where the finals were set in stone in mid-November, barring a major injury (Pistons-Spurs). No other sport has this problem. And it’s a problem. Everything else is great — likable young stars, more scoring, a drug-testing program that prohibits guys from playing with earth-shattering levels of residual THC in their system.… You couldn’t ask for much more. Except a competitive league.
Given how glorious your childhood was with the Celtics, how bummed are you that they seem locked in numbing, permanent mediocrity?
Simmons: I am constantly bummed out. I am never not bummed out about this. I feel like we used up 100 years of good karma in the first 30 years, then the wheels came off. We’re coming up on the 20-year anniversary of Lenny Bias’s death. He was like the patient zero for this ongoing debacle. By the way, thanks for bringing me down.
I’m sure you toggle back and forth, but if you had to choose one right now, would you watch a Celtics game or LeBron James?
Simmons: I’d watch the Celtics. They’re like having an uncoordinated son: Maybe they suck, but you still go to the Little League games and support them.
Has marriage and family lessened the allure of the gentlemen’s club?
Simmons: Yes. There are two big problems here. First, I hate turning people down, for any reason. It always makes me feel bad when I’m sitting there hanging out with a buddy, drinking a $12 beer and watching some naked chick rape a pole on the stage, and then the six-foot-two stripper with stretch marks who looks like Randy Johnson comes over and tries to snooker one of us into a dance. So you have to lie and say, “Sorry, I just had one!” Or, “Maybe later.” Or even, “I can’t. My jeans are covered in semen right now.” I always feel terrible. Deep down, they know the truth: I don’t want a dance because they look like Randy Johnson. And second, all the strippers wear that pungent perfume. You can’t get that scent off your clothes unless you wash them or burn them. And my wife is absolutely smart enough to smell my clothes when I come home from Vegas, and she absolutely would stab me in the middle of the night. So I’m basically screwed. If they ever opened a strip joint where nobody wore that skunk perfume, it would be the most packed place in town.
Hypothetically, then: You’re at the Olympic Garden in Vegas, fresh off winning $2,000 at blackjack. What does the Sports Guy look for in an exotic dancer?
Simmons: Someone who doesn’t smell like they just covered themselves in cherry air freshener from a car wash.
As you get older, which excites you more: 36-24-36 or .300-.400-.900 batting average-OBP-OPS?
Simmons: I would be more excited for the 36-24-36, because women aren’t built like that anymore. None of them eat, and everyone chain-smokes relentlessly. So the figures that we grew up ogling don’t exist anymore. When I’m president, one of my goals will be to make women eat fried foods again. Just look at poor Jennifer Aniston: She was a pantheon babe on Friends; now she’s just a giant head with little stick appendages. Where did her boobs go? Why would you want to lose boobs like that?
If your wife, the Sports Gal, granted you one free pass, who would you choose?
Simmons: The funny thing is, up until April of last year, I would have said Katie Holmes. Does that make me gay? Now I would go with Angelina Jolie. She’s like a smoldering volcano. I’m convinced that she should be our next president. She could convince any man to do anything. Even women want to make out with her. At the very least, she should become the commissioner of baseball — she’s the only person who could convince the big-market teams to have revenue sharing and a salary cap.
“I support any gambling. I wish we could gamble at weddings, strip joints, bachelor parties.”
If you had to reciprocate, who would you want your wife to choose?
Simmons: Either Mike Ditka or Bob Dole.
Where do you stand on the Texas hold ‘em craze: can’t end soon enough, indifferent, or hope it goes on forever?
Simmons: I hate the overexposure, and I don’t think it’s going to last, but it’s fun for people like me who know how to play poker — I always win at the tables now. All these online poker freaks have no idea how to play when they’re sitting at the table. They’re easy to read, and they can’t read anyone else because they’re used to guessing what complete strangers have in their online poker room that they can’t see. Easy money.
What’s your favorite sporting event to wager on?
Simmons: Playoff football: separates the men from the boys. Least favorite: the NHL. You just feel dumb saying things like, “Yeah, I have the Blue Jackets getting a goal and a half tonight.” But I support any gambling. I wish we could gamble at weddings, strip joints, bachelor parties, you name it. For instance, I went to a wedding a few years ago where I wagered with someone that the best-man speech would suck. And it did. I won two rounds of drinks.
Which would you most want to do: hit the World Series–winning walk-off homer, à la Bill Mazeroski in 1960; stick the championship-winning three-pointer, à la John Paxson in 1993; or thread the Super Bowl–winning touchdown pass, à la Joe Montana in 1989?
Simmons: I’d choose the walk-off home run because of the whole “Round the bases with your arm raised, flip the helmet coming around third base, then jump into the happy pile of teammates at home plate” thing. That looks astoundingly fun to me. We should be able to bid on this experience on eBay.
You’re wired into pop culture. Please explain why more than seven people watch Dancing With the Stars.
Simmons: It’s the same phenomenon as Jay Leno being the No. 1 late-night show, NASCAR being wildly popular, or slot machines generating a kajillion dollars of casino income. I’m sure it’s true — I just don’t know anyone who likes any of those things. People always forget there are, like, 250 million people living in America. I remember being on a plane once and reading a book. I kept hearing everyone laughing, so I looked up and the TV was showing some Tonight Show rerun. I looked around, saw the people on the plane, and thought, Ahhh … now it makes sense.
Which do you prefer: the scripted Lost, or reality juggernaut Survivor?
Simmons: I love Lost, but Survivor has been delivering the goods for six years now. It’s the perfect metaphor for life — people gaining the trust of other people, screwing them over, pretending to feel bad about it, then cashing a giant check in the end.
Name your favorite movie of last year.
Simmons: I loved Into the Blue — Jessica Alba scuba diving, Scott Caan trying to seem tall, Paul Walker doing his poor man’s Keanu impression, and Josh Brolin trying to play an evil bad guy with facial hair. That movie really brought everything to the table. We need to create the Bad-Yet-Enjoyable-Movie Oscars — that would have swept every category. Plus, it would be fun to see Keanu get the lifetime-achievement award. Come on, you wouldn’t watch that telecast?
Which is tougher: writing comedy with tape-time approaching on a late-night show or filing a column on deadline?
Simmons: Writing comedy was much tougher, only because you’re sharing an office with a bunch of lunatics who are farting and throwing Nerf footballs around and finding porn on the Internet and trying to distract everyone else who’s working. It’s like writing, but with a degree of difficulty attached.
Is it true that Jimmy Kimmel grills pizzas and makes calzones for his pals on NFL Sundays? Hard to imagine Letterman doing that.
Simmons: Only his friends and family know this, but Jimmy answers the age-old question, “What would Martha Stewart be like with a penis and a sense of humor?” And the answer is this: “Quite delightful!”
You’re alone in your car: Howard Stern on satellite radio with no commercials, or your pal Adam Carolla on terrestrial radio with 26 minutes of ads an hour? Be honest.
Simmons: I would always choose Carolla over Stern. He’s the only person I know who loves bad movies as much as me. This is a guy who can discuss Quicksilver for 45 solid minutes. I’m not kidding. I’ve seen him do it.
Back to baseball for one more question. We’ve heard lots of conflicting percentages, but in your gut, how prevalent do you think steroid use was in baseball at its peak?
Simmons: I’d say three out of every ten guys. It’s amazing there weren’t more basebrawls. I think ‘roid rage is overrated.
We cannot speak for ‘roid rage from personal experience, but having seen many movies, it sure seems like droid rage might be even worse. As for Bill Simmons, he continues to break new ground and get people paying attention while he does so. We just know that whatever venture he decides to get into next, we hope he calls us so we can get in early. … Of course that would be a huge surprise, seeing as how as far as we know he has never called this office before. Sad, really.
