Lev Grossman writes about books and technology for Time magazine. He’s also the author of the bestselling novels The Magicians and The Magician King

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• “One Man’s Quest to Outrace Wind,” by Adam Fisher, Wired

Why do I never find stories like this? Probably because I’m not working as hard as Adam Fisher. Apparently there’s this whole subculture of dirt sailing: people who race wind-powered vehicles on land. Apparently this one guy announced that he’d figured out a way to build a dirt boat that, while sailing directly downwind, can go faster than the wind that’s propelling it. Impossible, right? This whole insular community of dirt sailers got up in arms about it. But no. It was not impossible. You just have to be really, really clever to figure it out.

• “Adventures in Depression,” by Allie Brosh, Hyperbole and a Half

Writing about depression is hard, for the simple reason that when you’re depressed you can’t write, because you feel worthless, and who would want to read something written by a worthless person? I don’t know who Allie Brosh is, but this hybrid essay — half words, half pictures — gets as close as anything I’ve ever read to describing it. 

“Ads of Dragon,” by James Maliszewski, Grognardia

I’m cheating a bit here, because this is a series of posts rather than one single longread, but it’s important that people know about Grognardia, because it is the shit. Maliszewski writes brilliant and incisive essays about old-school role-playing games like Dungeons & Dragons. Most people who go down that rabbit hole lose the ability to write about gaming with any real perspective, because when you’re obsessed with something, you lose all perspective about it. (I speak as one has been down that hole.) Somehow Maliszewski hung onto his, and it shows in this glorious series, in which he analyzes a series of ads that appeared in the gaming magazine Dragon back in the 1980s. 

• “Did My Brother Invent E-Mail With Tom Van Vleck?” by Errol Morris, The New York Times

There isn’t anybody else quite like Errol Morris. I thought of him as a filmmaker before I started reading these essays that he posted on a New York Times blog. They’re not flashy writing, but his patient, unhurried, relentless pursuit of truth is a model for anybody who’s trying to tease apart a historical mystery crawling with ambiguity and unreliability. Here the mystery concerns Morris’s brother Noel, who went to MIT and was part of the very early computing scene in Cambridge the late 1960s, when the protocols of the proto-Internet were being hashed out. Morris’s brother died young, and Morris interviews his colleagues and goes through his notes to try to figure out whether he and his collaborator were the first people to use e-mail. I won’t spoil it for you.    

“Peyton’s Place,” by John Jeremiah Sullivan, GQ

Sullivan is my favorite magazine writer right now, bar none. Here he talks about the fact that his house was regularly used as a location for the filming of the soapy teen show One Tree Hill, and what that felt like. Which is something I would find inherently interesting anyway. The fact that Sullivan is the guy telling it and feeling makes it something more: An Important Fable for Our Time. Whatever Sullivan writes about automatically becomes a portal into the black soul of our stupid culture, and he gazes into it and somehow manages to remain calm and funny and smart while he reports back about what he sees.