When Aubrey Fox and I were promoting Gradual, we were occasionally asked about our writing process — co-writing a book is somewhat unusual and a few people wanted to know how we split up the work. Sadly, no one ever asked us anything else about the topic. I think that most people just aren’t that interested in the actual craft of writing, at least not when it comes to nonfiction.
Writing nonfiction is massively easier than writing fiction, but that doesn’t mean it is easy. To come up with a unique insight and then to express it in a way that is clear and convincing is a challenge, particularly in an era of tribalism and fan service when so many people (myself definitely included) are primarily interested in having their prior convictions reaffirmed.
Against the odds, it feels like we are living through a golden era in terms of the kind of nonfiction writing that I like — criticism, essays, and political polemics written with a lack of ostentation and a glint of humor. Here are some of my favorite practitioners of the art:
Caitlin Flanagan: The first word that comes to mind when I think of Caitlin Flanagan, a staff writer at The Atlantic, is “killer.” I find her writing surgical and merciless. Actually, that’s not quite accurate. What I really appreciate about her is that she is capable of both sticking a shiv in between the ribs and throwing an arm of compassion around someone’s shoulders, sometimes when you least expect it. Her essay about social media influencer Caroline Calloway captures both traits. She spends much of the first part of the article in shiv mode. For example: “Caroline Calloway is the kind of friend who, even if paired with a relative equal, could atomize your ego in less time than it takes to order a double macchiato.” By the time you get to the end of the piece, Flanagan hasn’t forgotten Calloway’s compulsive narcissism, but she has switched gears, crediting Calloway for being a self-created woman capable of “thoughtful and sensitive observations” about art and culture. Reading the essay, I felt off balance the whole time, in a good way. So many writers signal what their take is up front and then relentlessly pound it into you over and over again. In contrast, Flanagan keeps us on our toes, constantly excited about where she will go next.
Kat Rosenfeld: Like Flanagan, Kat Rosenfeld is capable of delivering a shiv straight to the ribs of her chosen target. In her recent review of Molly Roden Winter’s memoir of an open marriage, for example, Rosenfeld offers this memorable line: “Polyamory is a pile of lemons from which she relentlessly makes pitcher after pitcher of barely palatable lemonade.” Rosenfeld's beat is gender, sex, and culture, a treacherous terrain that she navigates with remarkable confidence, particularly since being an essayist isn’t her full-time gig. (Rosenfeld is a novelist who has written several mysteries.) In general, I think this is a helpful heuristic — if someone is a successful novelist, the chances are good that it will be worth reading their nonfiction (see: Zadie Smith, Jonathan Lethem, David Foster Wallace, George Saunders, Michael Chabon).
Kelefa Sanneh: The New Yorker’s Kelefa Sanneh is the rare writer who has directly changed my mind about something — his affection for country music helped me listen to the genre with a fresh set of ears. Eric Church, the Brothers Osborne, and Dierks Bentley have been in heavy rotation at my house ever since. Sanneh is a music writer with catholic taste; while his roots are in punk rock, he writes passionately about hip-hop, pop, dance music and other genres. His other great passion is boxing, which I must confess doesn’t interest me quite as much. It is also worth seeking out Sanneh’s writing on race — he authored a particularly incisive take on Ibram X. Kendi and Robin DiAngelo, for example.
Amy Lawrence: I have loved a few sports teams in my time — Joe Gibbs’ Redskins and the 1999 Knicks stand out — but no team has ever occupied a larger space in my heart than Arsenal Football Club. I’d be embarrassed to reveal how much Arsenal-related media I consume on a weekly basis. (I particularly recommend The Tuesday Club podcast and the Simpsons Arsenal Twitter feed.) The all-time greatest Arsenal writer is, of course, Nick Hornby, author of the classic Fever Pitch, which would deserve a place on the Mt. Rushmore of books about soccer if one is ever constructed. Unfortunately, Hornby doesn’t write much about Arsenal these days, so my go-to writer for all thing Arsenal is The Athletic’s Amy Lawrence. Lawrence manages a neat trick: she is an unabashed Arsenal fan but you never get the sense that she has left her critical faculties behind when she analyzes the team. And because she has been writing about Arsenal for decades, her access to information and interviews often trumps her rivals.
John Hollinger: I originally subscribed to The Athletic just so I could read John Hollinger. For me, he is the closest we’ve come to replicating the great Bill James. I read Bill James’ Baseball Abstract religiously when I was a kid, not because I was a big baseball fan or because I cared deeply about statistics, but because he was such a lively writer. James was someone who obviously thought about the game more deeply than just about anyone, but instead of using his knowledge to alienate or intimidate, he wrote in a way that welcomed non-experts to the party. Plus he had an irreverent wit that suggested he didn’t take baseball, which has long attracted a lot of pious windbaggery, too seriously. Hollinger has all of the attributes that made James so special. While Hollinger is best known for helping to popularize advanced NBA statistics, I never feel like I need a PhD to keep up. My love affair with the NBA is currently at a low ebb, for a variety of reasons, including an over-emphasis on scoring. (The dismal NBA all-star game will hopefully encourage the league to self correct.) At this point, I read Hollinger more than I watch the actual games.
Matt Yglesias: Beyond the fact that he is an eloquent spokesman for a brand of moderate liberal politics that I happen to share, what I admire most about Matt Yglesias is the sheer volume of material that he puts out into the world. My god, how does he do it? More or less every other day, Yglesias posts a new piece on his Substack newsletter. And these aren’t dashed-off 800 word columns where he compares contemporary political figures to some HBO or Netflix show he just saw — these are deeply-researched investigations of complicated and (sometimes) esoteric topics. And somehow he also finds the time to tweet constantly (and provocatively) too. A true workhorse.
Thomas Chatterton Williams: I loved Thomas Chatterton Williams’ 2011 coming-of-age memoir Losing My Cool so much that I gifted it to my nephews when they reached their early twenties. Since then, he has become a prolific cultural critic, writing for The Atlantic and other outlets about art, race, and politics. He is perhaps most well known for helping to organize the “Harper’s Letter” — an attempt to push back against the suffocating intellectual climate of 2020. Actually, come to think of it, this is another effective heuristic — if a writer signed the Harper’s Letter, chances are good that they are worth reading.
William Deresiewicz: William Deresiewicz writes about a broad range of topics, including the flaws and blind spots of the liberal elite that holds cultural and social power in the US. Deresiewicz’s critique comes from within the house — for years, he helped educate budding members of the elite at Yale and Columbia. Although he is a man of the left, Deresiewicz is willing and able to call out absurdity and sloppy thinking wherever he sees it. To get a sense, check out his piece “There Is No Right Side of History,” a thorough frisking of a piece of progressive rhetoric that has always annoyed me. (I complained about the expression in this piece for The Hill.)
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Having written more than I intended, I now realize that I have only scratched the surface — there are many other writers that I like that I haven’t included on this list. I will probably do another pass down the road.