For those of who have seen his popularity swell into the stratosphere the last few years, it wasn't a surprise to see Bill Simmons atop the bestseller list. But it should have been.
Daulerio will never admit this, and I probably shouldn't, but on January 23, 2003, we, along with fellow Black Table editor Eric Gillin, a Boston guy, stayed up to watch the debut of "The Jimmy Kimmel Show." We did this solely because Bill Simmons was a writer for the show. I'm not sure what we were expecting to see: Late-night talk shows aren't in the habit of giving guest appearances to lower-tier writers in their first episodes. (The show was a mess: This is back when they were openly drinking on set, and it was chaos. I think at one point, Kimmel tried to deep fat fry a ventriloquist dummy while "guest" Adam Corolla plaintively attempted to remind a piss-drunk Kimmel that "YOU ARE ON TELEVISION RIGHT NOW.") But it felt important somehow. A television show smart enough to hire Bill Simmons to write for them, well, that was something we couldn't miss. We felt like we knew him.
It's easy to forget this now, now that sports blogs are everywhere, now that Simmons is as much of an establishment figure as Chris Berman, now that the man produces his own television show, but back when he first came to ESPN, in 2001, he seemed like a revolutionary figure. I remember working in a doctor's office in May 2001 and reading his Is Roger Clemens the Antichrist? column. (I was not familiar with his Boston Sports Guy work.) I couldn't believe someone was getting away with this. Today, phrases like "kicked in the gonads," "this was the musical equivalent of U2 asking for a contract extension from their record company on the heels of "Zooropa" and "Pop")" and "looking like he was auditioning for the 'Chris Farley Story'" are familiar Simmons tropes: Everyone writes like that now. But not in 2001. In 2001, Skip Bayless was the "hip" columnist at Page 2. The other column I vividly remember from the period was Simmons' guide to the Atlanta Gold Club trial, which featured graphic descriptions of Patrick Ewing receiving oral sex from two women and this immortal aside:
During [Andruw] Jones's susbsequent testimony, the prosecutor asked which of the women Jones had sex with, and Jones answered, "Both of them," adding, "to tell you the truth, I wouldn't remember one of their faces right now." One of my personal favorite quotes from the trial.
What Simmons was doing was so different from what anyone else was doing that it didn't even seem to be the same medium. They were letting him do this? (Eventually, they would stop, somewhat: That Gold Club column got a solid scrubbing from ESPN back in 2007.) Other sportswriters hated Simmons immediately, ostensibly because of those tired Doesn't Sit In The Press Box arguments, but mostly because he was connecting with people, he was proving that the empty Verse Chorus Verse of the inverted pyramid and Fire The Manager! wasn't going to cut it anymore. Simmons was talking about sports the way people actually talked about sports. It's no wonder he was so disliked by the insiders and so embraced — tentatively at first, like a viral meme that spread, have you seen this guy? — by the masses. He gave hope for a lot of people — including, yeah, me, and Daulerio, and Gillin — that maybe the landscape for this shit, maybe it existed.
That turned, of course. It always does. Eventually the obsessives began carping — I think the Red Sox winning the World Series in 2004 was when the minor Bill Simmons Is A Douche! movement began — and the mainstream folks, unable to deny his success any longer, began meeting him halfway, featuring him above everyone else on the site and encouraging their own writers to impersonate him. (That Rick Reilly sits next to Simmons on ESPN.com's front page today is wonderfully surreal: No one's reputation as Sports Wit suffered more from Simmons' ascendance than Reilly. He morphed from Jim Murray to Henny Youngman, seemingly in a matter of weeks.) Sports blogs blew up, including this one, sites that put the Establishment (whatever that was) in their crosshairs and started firing, ultimately blasting in every possible direction, no matter what got hit. Inevitably, Simmons would become a target. He was the biggest name — to us, anyway. But even in those attacks, sometimes justified, sometimes not, there was always a little bit held back. After all, everyone still read Simmons: No matter how many Karate Kid and Teen Wolf references there were, you still always read him. You still took him seriously, even if it were to trash him. Nobody does that with Jay Mariotti, or Bayless, or Reilly. (Honestly, when's the last time you seriously read anything by those guys?) They're easily dismissed. They've been mailing in their work for a decade. No one has ever accused Simmons of that.
A large part of Simmons' appeal has always been that sense that you knew him, that somehow you were invested in his success. Malcolm Gladwell and Chuck Klosterman will sell more books in their lifetime than Simmons, but people don't wait in lines spanning around the block just to have them sign their book like they do for Simmons. (A search for photos of Simmons brings up hundreds of shots of him posing with fans.) People want to know what his wife's like — type "Bill Simmons" into Google, and the second hit is "Bill Simmons wife," and the fourth is "Bill Simmons wife picture" — and what his kids are like and whether he's different in Los Angeles than he was in Boston. This is all absurd, of course. The guy types into a computer at a coffee shop all day. But it's what fans have always done with Simmons, even those who purport to hate him. Simmons turned into an indie rock band from the early '90s. "He's hanging out with Jimmy Kimmel and Matt Damon now? SELLOUT!" We treated Simmons like he was a guy from our neighborhood who made it big, like it was important that he remember the little people who got him there. In a way, he kind of was.