Symposium

The book I've reread the most is The Odyssey. For a long time, I've read it once every year. Another book I've read many times is Eco's Foucault's Pendulum. I've read Asimov's cycle of Foundation many times. Don't know how many, actually. I've also read several times some philosophy classics, particularly Plato's Symposium, Phaedrus, Apology and Republic. Then there are many books that I've read at least twice, almost all considered classics (from 1984 to LoTR, Great expectations to Tom Sawyer, Crime and punishment to Twenty thousand leagues under the sea, etc).

Plato - Meno, Symposium, Parmenides, Gorgias, Protagoras Plotinus -Enneads Markus Aurelius - Meditations Descartes - On method Descartes - Meditations Spinoza - On the improvement of Understanding Leibniz - Monadology Leibniz - Grace Voltaire - Candid Diderot - D'Alembert's Dream Kant - How to orient oneself in thinking Kant - Critique of Pure Reason Kant - Critique of Judgment Hegel - Phenomenology of Spirit Hegel - Logic von Kleist - Marionette Theatre Kierkegaard - The Sickness Unto Death Heidegger - Being and Time Sartre - Being and Nothingness Sartre - Flies Sartre - Nausea Deleuze - Difference and Repetition Kafka - Metamorphosis Kafka - The Castle Lem - Magellan Nebula Lem - His Master's Voice Cioran - A Short History of Decay Pessoa - Book Of Despair Wolfe - New Sun tetralogy

I would not recommend any compilations of philosophy. The great thing about philosophy is reading the rationales and the results, not only the results. "Ricard+Revel - The Monk and the Philosopher" http://www.amazon.com/Monk-Philosopher-Father-Discuss-Meanin... (http://www.amazon.com/Monk-Philosopher-Father-Discuss-Meaning/dp/0805211039) "Socrates(/Plato) - The Allegory of the Cave" http://www.historyguide.org/intellect/allegory.html "Plato(/Socrates/others) - Symposium" http://www.amazon.com/Symposium-Plato/dp/0872200760 "Bertrand Russell - The Conquest of Happiness" http://www.amazon.com/Conquest-Happiness-Bertrand-Russell/dp... (http://www.amazon.com/Conquest-Happiness-Bertrand-Russell/dp/0871401622)

Being a programmer, you've probably felt the appeal of Platonism, so I'd recommend a couple of his dialogues: Phaedrus, Symposium, and the Republic (in order of length, short to long, since they are pretty dense). I'd also recommend reading the Republic last, so you can get over the misconceptions you were probably taught in high school. Allan Bloom's Closing of the American Mind is also very enlightening for a) understanding the goals of the enlightenment, and b) understanding the current state of our culture.