Here is a subset of the books that I read and enjoyed, clustered with a very weird distance function.

Biographies

Alan Turing: The Enigma

Einstein: His Life and Universe

Benjamin Franklin: An American Life

The Innovators: How a Group of Hackers, Geniuses and Geeks Created the Digital Revolution

Philosophizing

The Birth of Tragedy

Existentialism Is a Humanism

Godel, Escher, Bach: An Eternal Golden Braid

The Doors of Perception

Ill Fares the Land

Zero to One: Notes on Startups, or How to Build the Future

As We May Think, To Save Everything, Click Here, Who Owns the Future?

The Beauty Myth, Class: A Guide Through the American Status System

Beyond Culture, The Denial of Death

Fiction

The Little Prince, The Catcher in the Rye

Death in Venice, The Hours, The Unbearable Lightness of Being, Middlesex

In a Strange Room, The Line of Beauty, The Sorrows of Young Werther, The Sense of an Ending

Heart of Darkness, Nausea, Blindness, The Stranger, The Bell Jar

Jailbird, The Sirens of Titan

Disgrace, Elizabeth Costello

Atlas Shrugged, Watchmen

To Live, Anna Karenina

Hitchhiker's Guide to the Galaxy, How Should a Person Be?

The Broom of the System, Brief Interviews with Hideous Men

On the Road, Swann's Way, Min kamp, #4

Life and Times of Michael K, Siddhartha, Logicomix: An epic search for truth

1984, Player Piano, Brave New World, Cat's Cradle, Slaughterhouse-Five