Highly recommended things!
This is my five-star list. These are my favorite things in all the world.
A few of these works have had an extraordinary effect on my life or way of thinking. They get a sixth star.
Design
Graphic design, information design
The Visual Display of Quantitative Information, Envisioning Information, Visual Explanations, Beautiful Evidence by Edward Tufte: The bibles of information design. Nothing comparable exists.
A History of Graphic Design by Philip Meggs: History is the best distinguisher of fashion from fundamentals.
The Elements of Graphing Data by W. Cleveland: How to present data, and the why of the how.
Logic & Design in Art, Science, & Mathematics by Krome Barratt: A bizarre and fascinating tour de force of analytic design.
Understanding Comics, Reinventing Comics, Making Comics by Scott McCloud: The pedagogical potential of the comic form is vast and mostly untapped.
Industrial design
The Design of Everyday Things by Don Norman: Design as cognitive science.
Designing for People by Henry Dreyfuss: Memoirs of one of the founders of industrial design.
Cradle to Cradle by McDonough and Braungart: Manufacturing is compatible with global ecology.
Interface design
The Inmates Are Running the Asylum by Alan Cooper: The book that got me here.
About Face 2.0 by Alan Cooper: The first compre-hensive treatise on interface design.
The Humane Interface by Jef Raskin: Another classic analytic look at interface design.
Game design
Rules of Play by Salen and Zimmerman: The game design textbook. A comprehensive and insightful analysis of interactive design.
A Theory of Fun by Raph Koster: Why learning is fun, and fun is learning.
Chris Crawford: One of the earliest and deepest thinkers on game design.
Lost Garden by Dan Cook: Essays on creative and analytical approaches to game design.
Engineering
Software engineering
Structure and Interpretation of Computer Programs by Abelson and Sussman: The essence of software engineering.
The Little Schemer by Friedman and Felleisen: How to think recursively. One of the most unique and effective pedagogic books ever written.
Hacker's Delight by Henry Warren, Jr.: A treasure of bit-manipulation algorithms.
The Design and Evolution of C++ by Bjarne Stroustrup: Biography of a language.
Lambda the Ultimate: Everything I know about programming language theory, I owe to this site.
CiteSeer: Online library of research papers. Invaluable. Down with ACM extortion!
Dijkstra archive: Collected writings of one of the founders of computer science.
Programming languages
I've worked with fifteen or so programming languages over the years, and my tastes have changed a lot. I'm currently fond of these beautifully-designed languages:
Lua: A simple, elegant scripting language. Extensible and embeddable.
OpenLaszlo: Declarative layout, rapid prototyping.
Haskell: The programming language for the 21st century.
Languages that are inspiring to read about: Inform, io, Erlang, Fortress, Clojure
Math
Reforming the Mathematical Language of Physics by David Hestenes: The geometric structure of abstract nonsense.
Nonlinear Dynamics and Chaos by Steven Strogatz: Pictures, examples, geometric intuition. Greatest textbook ever.
Visual Complex Analysis by Tristan Needham: Complex analysis explained geomet-rically. Beautful.
Godel, Escher, Bach by Douglas Hofstadter: The formal systems, they are everywhere.
Invention
The Art of Doing Science and Engineering by Richard Hamming: How to do great work. How to think.
And Suddenly the Inventor Appeared by Genrich Altshuller: A delightfully insane introduction to systematic invention.
Inspiration
Folklore by Andy Hertzfeld: Anecdotes about the creation of the original Macintosh.
Society
Education
Mindstorms by Seymour Papert: This is how humans were meant to learn.
Dumbing Us Down by John Taylor Gatto: Why "schooling" is the opposite of "education".
How Children Fail by John Holt: Why "schooling" is the opposite of "education".
How to Survive in your Native Land by James Herndon: Why "schooling" is the opposite of "education".
Corporatism
The Corporation by Joel Bakan, et al: We've created a monster.
Ralph Nader: An Unreasonable Man by Mantel & Skroven: Portrait of a modern-day saint.
Progress
Technopoly by Neil Postman: Technological dependence, and the amorality of progress.
The Structure of Scientific Revolutions by Thomas Kuhn: This is how the world changes: with a bang, not a whimper.
Guns, Germs, and Steel by Jared Diamond: The birth of civilization and technology.
Media
Amusing Ourselves to Death by Neil Postman: Form limits function.
History
A People's History of the United States by Howard Zinn: The winners write the history books.
Lies My Teacher Told Me by James Loewen: The winners write the history books.
Art
Writing
The Careful Writer by Theodore Bernstein: Language porn!
The Mother Tongue by Bill Bryson: History of English.
RhymeZone: Superb rhyming dictionary.
Thesaurus.com: RogetŐs New Millennium, baby. That's how I roll.
Playing
Harmonic Experience by W.A. Mathieu: Tonal theory done right.
The World's Greatest Fakebook: The first one I reach for.
Alesis Micron: Makes a great stocking stuffer!
Listening
OverClocked Remix
8-bit Collective
The Wingless: John Burnett
Big Giant Circles: Jimmy Hinson
Stanford Harmonics
Humor
ytmnd
Sheepfilms
HappyToast
Fireland
Trigger Happy TV
Look Around You
Improv Everywhere
The Heuristic Squelch
Games
Orisinal by Ferry Halim
Knytt Stories by Nicklas Nygren
Braid by Jonathan Blow
Psychonauts by Tim Schafer
World of Goo by Kyle Gabler & Ron Carmel
Digital: A Love Story by Christine Love
Beyond Good and Evil by Michel Ancel
vvvvvv by Terry Cavanagh
Comics
Watchmen by Alan Moore
Nausicaa by Hayao Miyazaki
Fables by Bill Willingham
Re-Gifters by Mike Carey
Saturday Morning Breakfast Cereal by Zach Weiner
Truck Bearing Kibble by Kramer & Vaughn
Simulated Comic Product by Kevin Forbes
Perry Bible Fellowship by Nick Gurewitch
Married to the Sea by Drew and Natalie
xkcd by Randall Munroe
Octopus Pie by Meredith Gran
Cat and Girl by Dorothy Gambrell
Wigu by Jeffery Rowland
Narbonic by Shaenon Garrity
Spamusement by Steven Frank
Subnormality by Winston Rowntree