IF WE MEASURE our fondness for writers in purely qualitative terms—viz., by number of words read—then my favorite writer, by a wide margin, is Bill Simmons, aka The Sports Guy. Since discovering him in 2001 or 2002, I’ve read every piece he’s written, with few exceptions, for ESPN and now Grantland, the sports/pop culture site he founded two years ago. I’ve also burned through his two books, Now I Can Die in Peace and the mammoth The Book of Basketball. That’s a decade plus devouring a columnist who is both prolific and not afraid to devote 4,000 words to an arcane subject—Isiah Thomas’s incompetence as a general manager, say. By my (probably inept) calculations, he’s cranked out, and I’ve consumed, 1.5 million words in the last 11 years. That’s six Ulysseses.
The sports section, like the business section, is a place in the paper where the quality of writing takes on added importance, as the subject matter—who won, who lost, who played well and who didn’t; who made money, who lost money, which stocks rose and which fell—tends to be cut-and-dried. From the days of Grantland Rice (for whom Simmons’s site is named), there have always been terrific American sports writers. Tony Kornheiser, Michael Wilbon, Bob Ryan, the late Ralph Wiley, Sam Smith, Peter Vescey, Peter King—these guys are all fantastic. But they have all worked within an established idiom, the sports column. Simmons transcended that idiom. Playing on the advantages of writing online—no word limit, no subject too obscure to cover—Simmons reinvented how we think about sports. One of many examples: he conceived of “The Reggie Cleveland All-Stars”—players we assume are one race when we read their names, but turn out to be another race when we see them in person (the eponymous Reggie Cleveland, a former pitcher for the Red Sox, is a white dude). None of those other sports writers, not even Wiley, could have gotten away with slipping an observation like that in a newspaper column.
Simmons combines disparate elements in his work: humor, arcane pop culture references, comparisons of sports figures with TV characters, inventive features, an uncanny feel for the zeitgeist, and genuine insight into the world of sports. He’ll write a football column structured around lines he likes from The Wire, or spend thousands of words expounding on an out-there theory he’s come up with. He worries over the small things that true fans worry over but that sports pages tend to ignore. He’s creative, he’s funny, he’s smart, and he’s hopeful—he doesn’t resort to snark or put-downs. When I finish reading one of his better pieces, I am left with the same palpable sense of emotional uplift I feel watching a really good episode of a TV drama.
What sets Simmons apart is his angle. From the gate, his mission was to write about sports from the perspective of a fan, not an insider. Sports writers are journalists, after all, and like all journalists, they are dependent on their sources—more so, in fact, as a surly, antagonistic athlete can kibbosh a sports writer’s career. They venture into the locker rooms, they collect anodyne post-game quotes, they present the facts. When Simmons started his column, then called The Boston Sports Guy, for AOL’s Digital City Boston in 1997, he was liberated from these constraints. He could write whatever he wanted about Roger Clemens, because there was zero chance that he’d see Roger in the clubhouse the next day. His only relationship to the Rocket was as a fan. A big part of his appeal was his outsider, renegade status.
But for some time now, Simmons has been neither outsider not renegade. The first chink in the armor came in 2002, when he left his beloved blue-collar Boston for tony Los Angeles to write for Jimmy Kimmel Live!—after the host of that show actively recruited him. This is not an opportunity granted to outsiders. I was working an office job at the time, and was depressed when Simmons announced he’d be cutting back on his columns to write for Kimmel. I felt like my favorite co-worker had abruptly quit. Fortunately, he left the show after 18 months with a backlog of good material for his column.
In 2005, Simmons wrote a piece about playing H-O-R-S-E with Shaquille O’Neal. That the event was some sort of benefit organized by Nestle did not change the fact that a guy claiming to be an outsider was actively engaging with one of the biggest basketball stars in the world. I remember being of two minds about that column; enjoying it, but also concerned that it was a harbinger of an inevitable selling out.
From there, his career has only picked up speed. He’s been the most popular writer on ESPN, not exactly a small-time operation, for more than ten years. When researching his best-selling opus The Book of Basketball, he talked hoop with Magic Johnson, Larry Bird, Bill Walton, Phil Jackson, and his old nemesis Isiah Thomas, among many other roundball luminaries. He’s chummy with Malcolm Gladwell and Chuck Klosterman, Adam Carolla and Kimmel. He gets terrific guests on his podcast, The B.S. Report: SNL cast members, sports stars, big-time comedians, and a diehard Chicago Bulls fan named Barack Obama. By the time Grantland launched in 2011, The Sports Guy was more famous to sports cognoscenti than many of the athletes he was writing about. Once you’re interviewing the leader of the free world for your sports podcast, you are no longer a renegade.
While there are some fantastic writers on Grantland—Jay Caspian Kang and Alex Pappademas are my two favorites; read this and this—the sports content there can sometimes feel like Quentin Tarantino formed a development company with a gaggle of Tarantino imitators and only released films by Roger Avary and Gary Fleder. This does not stop me from reading it religiously. My main complaint is the same as everyone else’s: not enough Sports Guy.
This past year, Simmons joined the cast of NBA Countdown, providing studio coverage for ABC/ESPN during the basketball playoffs, one of a four-man crew that included Wilbon [1. I’ve been reading Wilbon since college, when we subscribed to the Washington Post, where he was a columnist. He even spoke to our journalism class. As superb as he is as a columnist, Wilbon is a better broadcaster, as co-host of ESPN’s excellent Pardon the Interruption], former NBA swingman and Fab Five Michigan Wolverine Jalen Rose, and Hall of Famer Magic Johnson. Simmons’s ascent to this lofty perch is remarkable, especially considering how few jobs like this there are. Fifteen years ago, he was working as a bartender, blogging about the Celtics in his spare time. Now he’s trading barbs with Magic on network TV. Hiring journalists to do studio commentary is not unprecedented—Peter Vescey of the New York Post filled the role ably ten years ago, and Stephen A. Smith always seems to be in a studio somewhere, yelling about nothing of interest—but none of his antecedents have made their name by presenting themselves as the Voice of the Fan.
Although he is telegenic—he has often written that he’d cast Matthew Perry as himself, which is a solid choice—Simmons is hard for me to watch on the telecasts. For one thing, I’d rather read him than listen to him; I feel like he’s Garbo speaking. For another, I know that him doing the show means fewer columns for my reading pleasure. As a longtime fanboy, I feel like one of those assholes who saw R.E.M. in Athens, Georgia, when they were still called Cat Piss, and who insist that they were never as good as they were when they recorded Murmur.
I try to think of Simmons as a mole, a secret agent, Our Man in the Wide World of Sports—like he’s me up there, living the life of (Pat) Riley; like he’s put one over on the powers that be; like he’s trying to change the system from within. But is he really? Or has a guy who built his reputation as Antiestablishment become the Establishment?
This is what worries me. What will renown—and its attendant boon, access—do to Bill Simmons? Like Walter White and Hank Schrader, his fame and his fandom have been on a collision course since the beginning. And like Walter White and Hank Schrader, they have finally collided. Will the Sports Guy be true to himself and do what he does best? Or will he, like Walter White, break bad? [2. This graf is representative of the sort of thing Simmons does, although he does it better than I do.] [3. Simmons loves footnotes.]
The closest analog I can think of to Bill Simmons is a brilliantly funny and versatile guy who started off his career as an outsider, who took a good decade to make it big, who began to make safe, boring choices the minute the money started rolling in, and who hasn’t been the same since. I speak of Benjamin Edward Stiller.
Ben Stiller’s first foray into the public consciousness was as the star and lead writer for The Ben Stiller Show, a short-lived sketch comedy program that also introduced us to Janeane Garofalo[4. When asked for advice on how to make it in showbiz, Garofalo said, “Meet Ben Stiller at the deli.”], Bob Odenkirk, Andy Dick, and Judd Apatow—a 1927 Yankees of comic talent. The show gave Stiller a platform to show off his considerable talents for mimicry. He gave us a terrific Tom Cruise, a spot-on Bruce Willis, and a Bruce Springsteen to die for. He was refreshingly and genuinely funny, and the show is well worth watching even now.
After the program was cancelled, Stiller flashed his versatility—always his greatest strength—directing Reality Bites and The Cable Guy, starring in the comedies There’s Something About Mary, Flirting with Disaster and Mystery Men, and delivering a fantastic and understated performance, against type, in Zero Effect—one of my favorite films of all time. It was an impressive run, although it did not yield the massive payday and name-above-the-marquee fame he would eventually achieve.
That all changed in 2000, when he starred with Robert DeNiro [5. A terrific actor, but a notorious sell-out.] in Meet the Parents, an insultingly insipid “comedy” built around DeNiro’s casual pronunciation of Stiller’s character’s name: Gaylord Focker. It was Stiller’s most successful movie to that point, at least in terms of box office, and its success clearly impacted him. He continued to do interesting work for a few years—the uneven Zoolander, which he also directed; The Royal Tannenbaums, also with Owen Wilson; and DodgeBall, a funny if lowbrow movie in which he actually created a character—but the die was cast. By the time Meet the Fockers, the inevitable sequel to Meet the Parents, came out in 2004, Stiller was in full-on sell-out mode.
To be fair, the line of demarcation is not indelible. There have been flashes of the old Ben: as Tony Wonder in Arrested Development, as an action hero in Tropic Thunder[6. In which Stiller directs Tom Cruise, who he obsessively parodied on his old show], as douchebaggier versions of himself in Curb Your Enthusiasm and Extras. But he has not been the same since he met DeNiro.
What drives me bonkers about post-2004 Ben Stiller is that I know he’s much more capable than what he’s done. I want to see him channel his 1991 self. I want to watch him be challenged, not do the same thing every time like that poster boy for comedian greed, Adam Sandler. Every Little Fockers is a waste of time better spent on projects worthier of his immense talents. All of this is easy for me to say, I realize. Who can resist a bigger payday for less work? Who wouldn’t want to make beaucoup bucks for being yourself? But Stiller, like The Sports Guy, is an entertainer, and dammit, I want to be entertained!
For Bill Simmons, the ESPN column is The Ben Stiller Show, Grantland is Tropic Thunder, Magic Johnson is Robert DeNiro, and NBA Countdown is Meet the Fockers.
The looming question is, where does The Sports Guy go from here? Will he be true to the maverick spirit of his AOL column, and remain the ultimate Voice of the Fan? Or will he fall in love with life as a studio talking head, and thus bow to his corporate overlords? He’s managed to toe the line for now, but eventually Hank Schrader will read the Walt Whitman book on the toilet, and Simmons will be forced to make a choice.
Is he one of us, or one of them?
Some insight into his thinking happened during an exchange Simmons had on NBA Countdown with Celtics coach Doc Rivers back in June. A former NBA point guard, Rivers is a likeable fellow with a winsome smile and an infectious laugh. He’s the sort of coach who excels at motivating the players in his charge, but not much of an Xs-and-Os guy. When Doc came to the Celts in 2005 after a successful stint for a lousy Orlando Magic team, Simmons—a huge Celtics fan—destroyed him in a 2006 column. Although he begrudgingly gave Rivers credit when Boston won the NBA championship in 2008, he was quick to excoriate him whenever anything was amiss. As a fan with decades of emotional investment in the team, Simmons just didn’t like the coach.
This past year, the window slammed shut on any hope for a Boston championship with the roster. Kevin Garnett and Paul Pierce were too old, Rajon Rondo was hurt, and the team was clearly headed for rebuilding mode. Meanwhile, in Los Angeles, the Clippers—for years the laughingstock of the NBA—were loaded with championship-caliber talent, but needed a better coach than the hapless Vinnie DelNegro, who helmed the team the last few years. Rivers wangled out of his contract in a deal that sent him to the Clippers for a draft pick. Soon after, Garnett and Pierce were traded to the Brooklyn Nets. Just like that, the proud Celtics were dead.
Simmons was not happy about this. He viewed Rivers as a snake in the grass, a double-crosser. And as the coach waffled about whether or not he was interested in the L.A. job, and whether or not he wanted to leave Boston, The Sports Guy fired off critical tweet after critical tweet. An example: “That rumored Celtics-Nets trade is so bad for Boston that Doc Rivers just quit on the Celtics again.”
This came to a head during the NBA Draft on June 27, when the two fired shots at each other on live TV. The feud escalated a bit when Rivers called out Simmons on a radio show, and Simmons again took to Twitter to defend himself.
“Look, Simmons is a fan,” writes Grant Hughes at Bleacher Report. “That’s always been at the heart of his appeal, but it’s starting to clash with his status as a particularly prominent member of sports media. His words carry farther, and now they reach the ears of not only the people he’s talking about (like Rivers), but also millions and millions of others.” The exchange taught Simmons “a small lesson in accountability and the price of real fame,” Hughes says. True enough. But what will Simmons learn from this brouhaha, in which a guy who left Boston for a better job in L.A. was critical of a guy who left Boston for a better job in L.A.?
As a fan of the old Bill Simmons, I love what he did. Studio commentators rarely say anything remotely controversial. Their insights tend to build upon the obvious. Wade is really laboring out there; I think his knee is bothering him or Tim Duncan looks like the Tim Duncan of old tonight. By attacking Rivers, then, Simmons violated a tacit rule of studio commentary. Put another way, when forced to choose, the outsider/renegade Sports Guy won the day. The Rivers imbroglio was vintage Simmons writ large.
The aftermath concerns me. Simmons laid low for awhile. He stopped tweeting about Rivers, and only referenced the spat on Grantland in a footnote to his column, weeks later (he and Doc talked it out on the phone; they’re fine). Did his corporate overlords take him to the proverbial woodshed? Will he do what they command, or will he continue to be himself? Is he part of the Establishment or not?
Like the fate of Walter White, it remains to be seen.
Last week, in his most recent dispatch, “The Eagles’ Greatest Hit,” Simmons offers an extended review of Allison Ellwood’s The History of The Eagles, Volume One, a new documentary he says he’s watched “five times, not counting all the other times it sucked me in for 15-minute stretches.” He continues: “I have participated in multiple Eagles-related e-mail chains that I may or may not have started. I have gone down Eagles-related rabbit holes on Google so cavernous that I once typed the words ‘Stevie Nicks Don Henley abortion.’ (Yes, things come up.)”
He is hardly an Eagles freak—he likes the Eagles as much as I like the Eagles, which is to say, as much as most people who don’t actively hate the Eagles like the Eagles—but he finds enough interesting in Ellwood’s film to demand multiple viewings. “In my humble opinion, it’s the finest documentary ever made about the rise and fall of a memorable rock band, as well as a superb commentary on the dangers of fame and excess.”
This is not a new topic for him. When dissecting sports, Simmons often writes about the dangers of fame and excess. It’s safe to assume that he’s thought about these things in the context of his own career. I’d go so far as to argue that “The Eagles’ Greatest Hit” is as much about Bill Simmons as it is about Glenn Frey and Don Henley. Certainly he’s thinking in those terms. He admits as much:
Even in the moment, the Eagles were painfully aware of their own creative mortality, that their success brought with it an accompanying shelf life of sorts. Like so many other writers, I worry about my own mortality all the time. What happens when I’m staring at an empty Microsoft Word doc someday and nothing comes out of my fingers, and that’s it? Tony Kornheiser told me once that, when he turned 43, suddenly he couldn’t write the same way anymore. He went to the well and nothing came up. From that point on, he never wanted to write anything. “It’s going to happen to you, too, Simmons — someday,” he told me. I hate that he told me this. Anyway, I identified with this part.
As much as I love Kornheiser, the Dave Berry of sports columnists in his day, I couldn’t disagree more with his prediction. Simmons won’t ever run out of things to say. As long as there is a popular culture, he will have plenty to write about. If he flames out, it won’t be because of writer’s block, like Kornheiser; it will be because he allows his fame to adversely affect his judgment, like Stiller. Case in point: Allison Ellwood isn’t a random stranger whose doc he caught one night on Showtime; she’s someone he has a professional relationship with. She directed one of the ESPN 30 for 30 documentaries, a series he helped create. This isn’t like me writing a glowing piece about The History of The Eagles; it’s more like me writing a glowing piece about Sean Beaudoin’s Wise Young Fool. Not that Simmons didn’t legitimately enjoy it, or that he shouldn’t have written about it, or that the Ellwood relationship wasn’t disclosed. But that essay is not the work of an outsider.
To be clear: I love Bill Simmons. There is a very short list of entertainers I would shamelessly embarrass myself gushing over [7. Bruce Springsteen, Quentin Tarantino, Elvis Costello, Winona Ryder, and Stephen Colbert, for starters], and Simmons is on the list. He has been since 2002—right around the time Ben Stiller was crossed off it. For my own selfish reasons, I hope that Simmons, having met his inner Fockers, will manage to defeat them, and won’t let them kill Bill.