Dan’s Top 100 Everything: #49 Bill Simmons


If you read about sports online, there’s about a 150% chance you have crossed paths with Simmons or his site, Grantland.

Simmons is one of the golden children of the ideals of online journalism and “sports blogging.” Regardless of how much you enjoy him, you have to admit he’s been influential in shaking up sportswriting in the Intrenet age.

Below are a few points on exactly what about his writing is so different from the norm — and key points to what make it so entertaining. Obviously, some of these have become less true has he’s risen the ranks at ESPN, but they’re all key points of his writing personality. For each one of these you can look at “traditional” sports journalism and see the stark contrasts:

  • Simmons writes primarily from the perspective of a fan, laying out his biases openly and never shying from them. He’s a Boston homer, and the first to admit it.
  • Because there’s no pesky layout to fit articles onto, articles can run as long as he’d like. This means articles and rants can go on for thousands of words.
  • Timeliness, while still important, is inessential. He can spend hours poring over video, interviews, other stories, and even books before writing about something.
  • He has the flexibility to wait until the muse calls to write. He can go two weeks without writing something, then publish three articles the next week.
  • Because his writing is from a fan’s perspective, watching the game at home or in the stadium, not a reporter’s in the press box, he doesn’t have to worry about offending players or coaches. He can speak his mind.
  • Ultimately, he’s his own editor. It’s up to him to decide if content is relevant or appropriate or interesting.
  • He has basically an unlimited amount of video, audio, and pictures at his disposal, and can embed it all into his article. He can link to pretty much any news story or book or interview he wants.
  • He doesn’t have to limit his writing to sports. He can make his articles a “grand theory of everything,” unifying pop culture and history and his own memories with his sports experiences.

Of course, those barriers are broken for anyone with a keyboard and an internet connection. What makes Simmons stand out is that he is a) extremely knowledgeable and passionate, b) tirelessly prolific, c) ambitious and creative, and — most importantly — d) a very entertaining writer.

For years, Simmons was an entertaining blogger and podcaster, but he swung for the fences in 2011 when he launched Grantland, an open-ended mega-site for in-depth sports and pop culture content. As a sports fan who also runs a site with the tagline “Taking a thoughtful look at arts, entertainment, and pop culture,” Simmons’ new site tickled me. Exactly the blend of content I look for.

Probably my single favorite thing Simmons has written is his 700-plus-page tome “The Book of Basketball,” one of the most entertaining sports books I’ve ever read. It at once captures Simmons’ playful spirit, riffing on theories and inside jokes, and serves as a nice primer to the NBA’s history and appeal. I’d recommend it just about any sports fan, whether you or not you think you’re a basketball fan.

But I enjoy — or at least tolerate — basically everything Simmons writes or creates. I read all of his articles, listen to all of his podcasts, and even keep up with him on Twitter. The enjoyability of my workday increases quantifiably when I get to listen to a Simmons pod or read a new article or something.

It’s true that there Simmons errs on the side of “fun” rather than “substantial” with some of his writing. His writing works best when it’s narrative- and emotionally-driven, like his tribute to his pet dog The Dooze (which has nothing to do with sports). He always gets carried away, but that’s part of the fun of his writing. He’s a good storyteller.

Right here is where I would praise the virtues and inspiration of Simmons’ independent, entrepreneurial spirit, the way he’s defined his career on his own terms. But — what do you know? — I already bored you all with that in my Louis CK entry to the Top 100. So go read that instead. Pretty much everything I said about the way I admire CK’s career applies to Simmons, too. He’s a positive, ambitious, creative-focused inspiration (as opposed to…) — even if he should shut up about the Celtics already.


Dan and Brian from Earn This now have a film review site and podcast:

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2 thoughts on “Dan’s Top 100 Everything: #49 Bill Simmons

  1. Here’s the difficult thing with Simmons: as you mentioned, he did play a significant part in changing the role of the ‘sportswriter.’ You have to give him credit for understanding that people would accept a biased writer, who wasn’t bound by deadlines, who wove pop culture into his musings, who perpetuated off-the-wall theories that sportswriters previously wouldn’t have touched, and who (by and large) was funny. And I love his passion for the NBA.

    That said (and maybe you don’t agree), he can be pretty insufferable a lot of the time. He’s better when discussing things that don’t require logical reasoning skills, but he’s hilariously bad when he has to actually think rationally about something. It’s comically easy to pick apart the flaws in his intellectual ‘arguments.’ For example, just read his columns or mailbags about the NBA – which he supposedly should know the most about – and try to find any actual analysis or insight. Hint: it won’t happen. He should stick to writing about Vegas trips and pop culture theories that loosely tie into sports. But he seems to want to spend too much time trying to force-feed us his sports arguments that aren’t particularly well thought out.

    /mini-rant over

    • I think I agree with you by and large. He’s on the “entertainment” end of the sportswriting spectrum, not the “analysis” end, for sure. I barely even read his mailbags anymore, just skim over them — they’re probably his weak point.

      It may not be what you’re looking for, but I really like the pods and articles where he talks/writes about the past of sports and how current stuff relates to that. You complained about this when we talked on Friday, how he always goes big and long when the moment sometimes calls for just focusing on what’s happening. But his podcasts with NBA legends are almost always his best. It’s fun, educational stuff, and you can tell the former players really open up when they sense the passion and knowledge he has.

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