I recently tried Elo ranking the book list I'd been keeping. Here are the books that came out in the top 25 when I ran a few hundred Elo matchups, with the question: 'which of these two books are you most glad to have read?'
1 - The Beginning of Infinity - David Deutsch
2 - Antifragile - Taleb
3 - Skin in the Game - Taleb
4 - The Black Swan - Taleb
5 - The Means of Ascent - Caro LBJ Book 2
6 - Fooled by Randomness - Taleb
7 - Master of the Senate - Caro LBJ Book 3
8 - Now It Can Be Told - Leslie Groves
9 - I Am a Strange Loop - Douglas Hofstadter
10 - The Passage of Power - Caro LBJ Book 4
11 - Poor Charlie’s Almanack - Charlie Munger
12 - The Path to Power - Caro LBJ Book 1
13 - Invent and Wander - Bezos' Shareholder Letters
14 - No Rules Rules - Hastings and Meyer
15 - 7 Powers - Hamilton Helmer
16 - Lest Darkness Fall - L. Sprague de Camp
17 - The Dark Forest (Three Body Problem Book 2/3)
18 - The Master and his Emissary - McGilcrist
19 - Three Body Problem (Three Body Problem Book 1/3)
20 - The Lord of The Rings - The Fellowship of the Ring - Tolkien
21 - The Score Takes Care of Itself - Bill Walsh
22 - Working Backwards - Carr and Bryer
23 - Sam Walton Biography - Made in America
24 - Talent - Cowen and Gross
25 - Stubborn Attachments - Tyler Cowen
I then did the same for the books on my to-read list. Here are the top 10 books when I asked: 'which of these two books do you think you'd be most glad to have read if asked one year after finishing it?'
1 - Founders at Work - Livingstone
2 - The Lessons Of History - Will Durant
3 - Romney: A Reckoning - McKay Coppins
4 - Good Strategy Bad Strategy - Rumelt
5 - Buffett: The Making of an American Capitalist - Roger Lowenstein
6 - The Fabric of Reality - David Deutsch
7 - Scaling People - Claire Hughes Johnson
8 - Working - Caro
9 - Godel Escher and Bach - Douglas Hofstadter
10 - Caesar and Christ - Will Durant
Two placeholders
1 - I'm planning to put the Elo tool I built up here to let anyone reading this play with it and produce their own top list. In the meantime, please do send me any recommendations I've missed and tell me what should be at the top of my to-read list! Feel free to email me at christian@christianholland.me and I'll also add recommendations to the list above. All the best books I've read have come from recommendations, and if you're reading this page I'm quite confident we'll have similar taste in books!
2 - I've been trying to become more obsessive about reading the best books I can find at any given time. The quality of books and their impact on me is definitely power law distributed so it's worth putting a lot of effort into finding the best ones. I've been meaning to write something about this: but haven't yet got around to it.
In the meantime this summary from John Collison seems like a great guiding principle.
There is a set of books that are enjoyable to read as you're reading them.
There is a set of books that you'll be glad to have read some years after reading them; they're practically useful, make you a better thinker and/or give you useful information.
The intersection of these sets, the books that you'll enjoy reading and that you'll be glad to have read, is more books than you could ever read in your life.
Therefore you really should work hard to always be reading the best book that you could possibly be reading.
This list by Patrick Collison is also an excellent starting point for finding books that are in that intersection.
With thanks to Lydia Field, Ruairidh Forgan, Manolis Carousos, Harry Coppock, Sammy Cottrell, Srin Madipalli, Edward Druce and many others for being an unfailingly great source of book recommendations.