Roughly ranked from most to least favorite within each section. (There’s an even longer list of books I decided not to read at all, so don’t be offended if you recommended one of the least favorites!)
History and politics
Team of Rivals (2005): Not that you need my recommendation, but it was as good as advertised, although I kind of skipped through a lot of the character-and-family-life stuff in the second half because it got repetitive and focused on the war and governing.
The Engagement: America's Quarter Century Struggle Over Same-Sex Marriage (2021): As far as I can tell this is the definitive read on the most interesting policy achievement of my lifetime, given how quickly public attitudes changed. There's a lot more detail on the specific personalities and conflicts than I really needed, but also important things I didn't know before. One that stands out: gay marriage groups expected to win rights first in friendly state governments, then to win in federal court, then finally for public attitudes to follow, because that was how interracial marriage played out; only in the late 2000s, when public opinion swung quickly in their favor while many state initiatives failed, did they essentially reverse that course.
Nixonland (2008): This is about a president who built a political base by slandering political opponents in baseless ways despite disapproval by party elites; who as a presidential candidate meddled with foreign policy to hurt the country but help his own campaign; who explicitly treated the mainstream press as the enemy (even as some liberals mocked the press focusing on how they were losing touch with middle America instead of holding him accountable); who constantly said absurdly self-refuting things; and who won an election despite ongoing scandal in part because the media balanced its coverage by overhyping much less important issues for the other candidate. He did this in a political climate in which police brutality against Blacks had caused massive protests and then a conservative backlash; an ascendant far-right wing crusaded against culture war issues by e.g. trying to ban a textbook for destroying American pride because it talked about racism; and an outsider far-left Democrat with a small-dollar base outperformed in their primary (especially the caucus states), leading to a nomination fight that was drawn out well beyond the point when the outcome was decided. So just a wee bit relevant to modern times.
The Swerve: How the World Became Modern (2011): A fun conceit—telling the story of one guy who rediscovered one old essay and brought it into intellectual circles that eventually produced the Renaissance—made it more lively than the typical history book. I learned that some values that seem obvious today (the universe is made up of atoms, we can understand it better through science, pursuing pleasure is generally good) weren't always condoned. But I didn't feel like the book really proved that this essay was as influential as it's portrayed here.
Lords of Finance: The Bankers Who Broke the World (2009): Very good as a general history of economic policy around this time and how it contributed to the Great Depression, but I didn't buy the thesis laid out in the title and blurb that these men individually changed the course of the world economy—the book said more about the constraints they operated under, and few of those individuals' decisions seemed surprising or different than what peers would have done. So I wished I'd skipped a lot of the lead-up on their biographies and everything through the end of WWI.
Paved Paradise: How Parking Explains the World (2023): As a history book, it's good; as a policy argument, it felt lacking. (I'm already YIMBY-pilled and agreed with the spirit, so maybe I'm not the target audience?) For a book published in 2023, it's curiously incurious about technology—a chapter on parking oversupply has a page that makes it sound like Spothero could solve all the problems, but then it just ends abruptly instead of diving into those; autonomous vehicles get only a page in the conclusion, and Uber even less of a mention, even though those could completely upturn what parking looks like.
Business and economics
Save Me the Plums (2019): I guess it makes sense that a great management book would be written by the EIC of a major magazine. It's not actually presented as a business book—it's mostly stories of personalities and food—but there's a lot about managing personalities and dealing with unexpected change.
Good Strategy Bad Strategy (2011): The framework at the front of the book is clear, powerful and important (which already puts it in the top 1% of business books). The anecdotes through the rest of the book are genuinely interesting and well-told, but it's not so clear how they actually link to that framework.
Financial Hacking (2012): It tries a little too hard to be fun, but I still found it useful.
Switch (2010): A typical business book—a style-over-substance framework, based on the semi-rigor of a bunch of findings you’d see in an intro psychology class (some of which have since been debunked, e.g. Brian Wansink’s food studies), but enough interesting case studies that it was worth skimming to pick out the good ones.
Business Adventures (1969): I picked this up after seeing somewhere that it was Bill Gates’ favorite business book, but it didn’t stand the test of time—the stories were tedious and pretty dull
Parenting
Parent Like a Pediatrician (2022): I read a lot of books the year before to prepare for having a newborn, but this one was by far the one that resonated best with my experience. The first book a first-time parent should read is probably one of the ones with “official” advice, but this should be the second one—the official recommendations aren’t always right for every family, and this book is very helpful for making those decisions.
How to Talk So Kids Will Listen & Listen So Kids Will Talk (1980): I'll re-read this once my kid is old enough to talk, but I really liked it. The strategies really seem like they’ll help converse productively with children, and the book was mostly examples (a good thing in this context), even if sometimes they seemed a little contradictory.
Nurtureshock (2008): In most popular science books, the first chapter is the only thing worth reading, and the rest is just filler. To my surprise, this book was the opposite—the first chapter was fine but pretty generic and based on slightly sketchy social science, but the rest of the book covered a lot of topics that were both useful and new to me (though for all I know they may have been based on slightly sketchy science too and I just wasn't familiar with it). Nothing really ties each chapter together, so it reads sort of randomly, but it was interesting throughout.
Bringing Up Bébé (2012): I never know what to make of books that were popular a decade ago and now seem to be arguing against strawmen—does that count against the book because it's making up positions to argue against, or does it count for the book because it caused people to act differently? It’s well structured for an “advice” book, because it gives some genuinely new frameworks for parenting and articulates them clearly; they're probably not all right, but this isn't the only book you'll read about parenting, so that's fine. But evidence is scant (and in most places obviously cherry-picked), and several sections with seemingly contradictory insights (particularly around how to prepare for birth and on risk tolerance while parenting) are never explored or resolved.
Fair Play (2019): Covers important concepts on invisible labor, although I see it as a Getting Things Done-style book that’s very useful to read but a bad idea to implement literally. It also could have easily been like half the length because so many points were repeated exactly.
The Manager Mom Epidemic (2020): The ideas were fine but the writing was weird and annoying.
Sports
Ball Four (1970): It held up a lot better than I expected, though now it's a work of history rather than an exposé of what life is like in the majors. Favorite how-the-times-changed anecdote: after Bouton got demoted to AAA, he wanted to bring the larger catcher's glove his teammate used to catch knuckleballs, but the rest of the major-league team was on the road, so he just hopped the fence of Seattle’s stadium and took it from the unguarded clubhouse.
The Lords of the Realm (1994): It's remarkable that the definitive read on MLB labor relations and ownership was published in the spring of 1994, just before a kind of big thing happened. The reporting and anecdotes are tremendous, with inside intel from seemingly every corner of baseball, making it a really fun read (especially in the later years).
Other nonfiction
On Writing Well (1976): If I had less writing experience I would have gotten a lot out of this. As it was, I pretty much already agreed with and try to use most of what's in here, but the examples and time to think about it are still helpful. The first third of the book has the best stuff, then it goes into different verticals that are mostly less interesting, except maybe the travel one.
A Swim in a Pond in the Rain (2021): Everyone says it’s one of the best books about fiction writing; that came through for me. I actually stopped reading halfway through because I want to come back to it some other time when I’m in a better mood to digest it.
How to Read a Book (1940): A topic that I was glad to think about deliberately, and advice that holds up surprisingly well—perhaps too well, as a lot of it has become conventional wisdom (if not always followed) in the intervening decades. I wrote much more on it here.
Barbarian Days (2015): One of those books that I’m afraid to admit I merely liked when everyone else seems to love it.
The Checklist Manifesto (2009): It would be higher if I was ranking books by their impact, but there wasn't much in here that I didn't know from all the other commentary that made me want to read the book.
Four Thousand Weeks (2021): I didn't get a lot out of this book, but I'm not sure if that's a comment about the book or about my mindset going into it. You can probably get more out of rereading the intro chapter a dozen times than out of reading the whole book; the second half in particular felt like filler.
The Human Network: How Your Social Position Determines Your Power, Beliefs, and Behaviors (2019): If you want to learn about network theory, this is a good book: it's readable, with lots of examples, and covers non-obvious but powerful concepts clearly. (You also have to give it credit for topical prescience: how many books published in 2019 featured a chapter on pandemics and another on bank contagion?) But it's really just about network theory—aside from a random, naive chapter about macroeconomics—which means it doesn't live up to the grand claims of the subtitle and summary. Put another way, I don't really think it's that useful to learn about just network theory. (Props for the #lastman reference though.)
How to be Perfect (2022): A light overview of some basics in philosophy, which I appreciated, but with a lot of trying-hard-to-be-funny-and-relevant, which I didn't so much. If you're a fan of Michael Schur like I am, you might enjoy this book; if not, I doubt you will.
Trick Mirror (2019): I loved “Reality TV Me” but was less enthused by the other stories.
The Bird Way (2020): I like birds a lot but honestly I found it pretty boring.
Fiction
Babel (2022): A wonderful blend of historical and science fiction, which I always enjoy and especially enjoyed here. I didn’t get to Yellowface this year but I’ve seen great reviews and it’s near the top of the list for 2024.
The Savage Detectives (1998): If I'd known what this book was about beforehand (and particularly how it centers a character based on the author), I wouldn't have read it, but I'm glad I didn't because I loved the writing. Most of it is structured as an oral history of two main characters who are never quoted, which sounds weird but works as a device to write the story in incredible detail.
This is How You Lose the Time War (2019): It took about half the book for me to figure out what was going on, but from then on it was beautiful.
The Woman in White (1859): I was about to give up 100-ish pages in, and then the mystery started to develop and I was totally hooked.
Put Out More Flags (1942): This was on my to-read list for 15 years and I've forgotten why, but I enjoyed it.
The Art of Fielding (2011): I avoided it for a while because "popular book centered on baseball" sounded like it would annoy me, but the baseball parts held up well and I liked the writing. I got a little annoyed by how the book was just too much—too many stories, too neatly intertwined, with too much happening too implausibly in each.
I Have Some Questions for You (2023): A lot about this book made me think I wasn't going to like it, but the page-by-page writing was good enough that I continuously wanted to keep reading, and the ending came through. (I picked this up because The Great Believers is one of my all-time favorite novels.)
The Remains of the Day (1989): I like it better thinking back on it than I did actually reading it, especially the ending.
All the Birds in the Sky (2016): I felt like the world-building was a little bit incomplete at times, especially around some of the key turning points, and I still don’t really know what happened at the end, but I liked the characters.
The Green Road (2015): The writing was really good, and I mostly liked the first half, but I lost interest by the end.
The All of It (1986): I just never got into it. The book jacket says it’s like Gilead,1 which I didn’t really like either but won a Pulitzer, so it’s probably just me.
Unrelatedly, the subject of the funniest review I’ve ever seen on Goodreads.
People who lived through Nixon often use him as a point of comparison -- sad to say , too often we say "Worse than Nixon"
I lived across the street from Watergate during break-in. Unlike Forest Gump, I didn't see a thing.
Very diverse and interesting; I never liked Gilead either (and felt I should have)
I'm already YIMBY-pilled and agreed with the spirit ( I love learning new acronyms...YIMBY is new to me) Pilled?