The challenges to picking the best Bill Simmons columns are twofold.
First, he’s prolific. There are hundreds of items listed on Simmons’ archive at ESPN.com spanning a variety of subjects: straightforward columns, movie reviews, profiles and features.
And second, he writes long. Even though he spent his formative years writing online for AOL Digital City, he’s more known for ruminative stemwinders than for terse blogging.
So, to help me cut through years and years of storied work, I relied on a few sources. Some members of Reddit established a comment thread dedicated to some of his best work. Rolling Stone compiled a great list last year, and The Big Lead just dipped into the archives to surface 20 of his standouts. Here are the seven indispensable columns I culled from those lists and a few hours of reading:
1. The nation’s destination: destiny
This column made both Rolling Stone’s and The Big Lead’s lists, which is no surprise. It’s a humorous, affecting play-by-play of a lifelong Boston Red Sox fan watching his team win the World Series:
Forget about ending the curse and having 86 years of baggage erased in one fell swoop. If you don’t get emotional watching a group of guys celebrating and hugging when you feel like you know them, when you suffered all the same highs and lows, when you spent the last seven months with them … I mean, why even follow sports at all?
(Translation: It’s getting a little dusty in here.)
8:43 — Best glass of champagne in my life.
8:44 — Just called my Dad. Been waiting to make that call my whole life. “It happened in my lifetime!” he keeps saying. As an added bonus, the apocalypse didn’t happen.
Ever wonder why a sports team has a sudden run of wins after one of their best players is relegated to the bench? Simmons explains this phenomena with “The Ewing Theory,” a dictum born from watching the Knicks band together after star Patrick Ewing was put out of commission by foul trouble or injury:
Dave introduced me to the Ewing Theory three years ago, and we’ve been tinkering with it like Voltaire and Thoreau ever since. Eventually, we decided that two crucial elements needed to be in place for any situation to qualify for “Ewing” status:
A star athlete receives an inordinate amount of media attention and fan interest, and yet his teams never win anything substantial with him (other than maybe some early-round playoff series).
That same athlete leaves his team (either by injury, trade, graduation, free agency or retirement) — and both the media and fans immediately write off the team for the following season.
Simmons updated the theory in 2013 when the Boston Celtics surged after Rajon Rondo’s season-ending injury.
On the way to announcing the launch of his new site, Simmons takes a detour through his own memory, regaling readers with a lengthy digression about his time working for Jimmy Kimmel Live. He compares the onset of creative terror prompted by starting Grantland to the anxiety of launching a late night talk show. Every journalist can relate to the fear and anxiety that accompanies bringing something new into the world, no matter how small.
I would love to tell you that this website will work, that we’ll entertain you five days a week and blend sports and pop culture successfully. The truth is, I don’t know for sure. This site will keep changing over the next few months just like Jimmy’s show kept changing in 2003, hopefully for the right reasons and not the wrong ones. We are still hiring people. We are still finding writers. We will eventually have a sports blog and a pop culture blog (launching next month), user comments (later this summer), a podcast network (ditto), a quarterly publication we’re doing with McSweeney’s (four a year, starting this winter), and who knows what else. You figure out what works, you figure out what doesn’t work, you keep moving. That’s the next nine months for us. Eventually, we will evolve into what we are. Whatever the hell that is.
In this column, Simmons addresses another form of writerly anxiety that journalists wrestle with: Are we doing our best to present the best obtainable version of the truth? For Simmons, the question boils down to a conflict between his raw sensibilities as a sports fan and his reputation as a fixture in the sports journalism community. That tension grows more acute as he considers whether to write about performance enhancing drugs, which he finally does:
ESPN Me didn’t have the balls to run two e-mails that you’re about to read. They nearly landed in each of my last four mailbags. Each time, I pulled both e-mails (and my responses) from those columns at the last minute.
In one of his most confessional columns, Simmons pens a heartbreaking eulogy for his beloved golden retriever, Daisy (or “The Dooze,” as she’s referred to in his columns). The column follows Simmons’ life with his dog, beginning when Daisy was a puppy and he was a newlywed, and ending with her death, the result of stage-five cancer.
The Dooze fought through the pain, rose to her feet, grabbed the ball, rolled it over to us, took a few wobbly steps backward and dusted off the “Come on, throw it to me” face. We tossed her a few from short range, then a few more. She caught every one of them. This was her last hurrah. She tired quickly and laid down again … and that was that. The doctor came in a few minutes later and euthanized her, with that same ball resting right next to her mouth. We had her cremated with it. We just thought it seemed fitting.
In this column, Simmons spells out the jubilation of a long-suffering sports fan upon discovering that his or her team has gone all the way. In this case, he exults after the Patriots defeat the Rams in the 2002 Super Bowl. The headline for this column eventually became the title of his book chronicling the path to the Boston Red Sox’ World Series victory.
Sitting behind me, an older Patriots fan had turned bright-red — I couldn’t tell whether he was laughing, crying or both — and he was screaming “Fifty years! I’ve been waiting for this for fifty years!” and “They gave us no respect! None!” And he just kept screaming those things again and again. And again. And again. Meanwhile, the other Patriots fans in our section were hugging one another and carrying on — none of us knew what to do. We were collectively incredulous. Total disbelief. Nobody could ever make jokes about the Patriots again. We had arrived.
This column is remarkable because Simmons ekes out a 4,000-word column after beginning from the premise that its subject, Tiger Woods, is simply too good to write about.
“Have you ever written a column about him?” Dad wondered.
“Nope. Never. Not in my entire life.”
“I don’t know. What can you say?”
And that has been the strangest part of the Tiger Phenomenon: What can you say? Watch him play golf, watch him dominate, watch the way he carries himself, watch the way the other golfers self-destruct around him … what can you say? Is there anything writers can possibly add?
This is a column about column writing, which makes it a particularly instructive read for journalists. Simmons explains the challenge of approaching a successful subject that has been profiled extensively and dominated the sports world with a deluge of positive press.