Well, another long post then.
General remarks
Your aims actually are not altogether compatible, assuming limited time.
To have read up on what an educated person should have read: depends whether it is a lay person or a philosopher. In the former case: most people have read very little actual philosophy first-hand. In the latter case: this amounts basically to doing a B.A. in philosophy, which is not a bad thing, but would take a lot of time.
Being able to read modern philosophers, in case they are not specifically aiming at a general audience, may also get close to requiring a full study, unless you are going to specialize in a specific branch. For ‘fashionable’ continental/french philosophy like Baudrillard (which I would not recommend) or Lyotard, Magill gives some of the basic information necessary to approach them. But these philosophers assume a general working knowledge of Kant and Hegel as well. And both write in a difficult style. Do you have specific names you wanted to read?
I would recommend to read with some kind of preference as guideline. Otherwise you may well find yourself stuck in some text that is boring you to death. The works you mentioned are mainly quite general philosophy of a kind that is rare in modern philosophy; that you did like them does show that you can digest the works I mentioned previously. The Machiavelli you mentioned indicates a taste for social/political philosophy.
If you don’t mind, I further have a few general remarks that may prove useful. Feel free to skip them.
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Philosophy in general is an on-going debate, which means that if you want to follow it, you do need, as you remarked, understand some of the history. For understanding modern philosophers you must be familiar with some of the jargon (epistemology, categorical imperative), have read certain key passages and examples, and be familiar with certain kinds of argument (such as social contract theory). It’s a bit like getting used to SDMB, understanding the in-jokes and terms like ‘whoosh’. Part of it you just learn by reading and understanding the gist of it from the context.
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For studying you may profit from going on in a way similar like a normal university study, only in a more condensed way. That means, reading secondary works to know the basic history and respective influences, interspersed with the most important bits of primary works to get first-hand experience. Many of the great works are almost never read in their entirety; only the good parts are well-read. The books that are commonly read entirely I’ve mostly already listed. So you should resign yourself that you will not read the full Critique of Pure Reason, but would try to read the preface, introduction, and par. 15-27 in the A and B version, accompanied by commentary such as the Solomon book I listed.
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Furthermore it is easier not to read completely at random, but try to have some historical and/or thematic coherence. Reading Hobbes, Locke, Hume and Rousseau will show you a similar looking argument treated in different ways.
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In a way, philosophy is not what you read, but more of a certain attitude in debates. You learn to distinguish different meanings of the same word (which may clear up lots of confusion, but also give rise to debat, think of the ‘What is a right’ debate in GD right now), and should be more willing to distance yourself from any preconceived notions if only for the duration of an argument. Plato discusses this in the Phaedo. Finally, philosophy may help you find others’ and your own preconceptions. You need this flexibility to properly read those primary works.
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When reading the work you can choose to follow the drift of the argument, but if you really want to understand what is going on and learn something from it, you will need to try sometimes to map the argument: what does the writer state, and how does he think he proves it?
Other than that, just try to have some fun. Don’t force yourself to read something if you really don’t like it, it will only spoil your appetite. Rather switch to another book, and try again later.
Additional recommended reading
Given what you mentioned in your last post, I would recommend to read primary works together with a secondary work by the side (or to switch books when you get bored with one). The primary works I’ve already mentioned would get you a long way. I would add the following.
- Hobbes, Leviathan. Don’t read everything, but at least par. 10-31.
- Rousseau, *Discourse on inequality * and Discourse on the arts and sciences. These are somewhat like Machiavelli’s Discourses.
- J.S. Mill Utilitarianism, another classic.
- Wittgenstein. The Tractatus Logico-Philosophicus is a must-read, even if it may be hard to follow. The Philosophical investigations is much more accessible; it is a collection of short fragments that are arranged into a more continuous argument. If so inclined you could start with this to get a taste of philosophy.
After having read through this list of primary works (but skip whichever you don’t want to read), you’d have experienced most of the great philosophers first hand. For Aristotle I recommend a secondary work with lots of original quotes: J. Ackrill, Aristotle the philosopher. After that you could try his primary works.
Some other great works that are among the classics, but which I would consider to be too hard are:
- Spinoza, Ethics
- Kant, Critique of Pure Reason
- Hegel, Phenomenology of Spirit
- Heidegger, Being and Time
- Sartre, Being and Nothingness
If you feel up to it, do go ahead and leaf through them, just to see what they are like. Parts of those are readable on its own, but you have to know which parts. Generally they are best approached with a basic general knowledge, a good commentary, and lots of patience.
If you’ve read all of the above you may still lack some knowledge for reading modern philosophy. Secondary works for specific subjects may fill a gap. The following need some time to properly absorb, so you may not want that. OTOH they do introduce all the common jargon of the specific subject.
W. Kymlicka, Contemporary Political Philosophy does an excellent job of lucidly reconstructing the argument of most modern philosophy. Unfortunately the second print is significantly and discouragingly thicker than the first print. He discusses Rawls, Dworkin, Nozick and others.
Ethics: J.L. Mackie, Ethics gives a short introduction. You can also try James Rachels, The Elements of Moral Philosophy.
Philosophy of language is probably too specialized given your stated objectives. Blackburn has written a book on the subject, though.
Philosophy of science: Ian Hacking, Representing and intervening is a good introduction.
Metaphysics. A highly specialized subject which may be too abstract to your liking (do you like to think about solipsism? the nature of existence? whether things are primarily form or matter?) but you should understand at least what it involves, and know the jargon. Furthermore it deals with some of the classic philosophical questions (do things exist if they are not perceived? etc.) The history by D.W. Hamlyn I mentioned covers some of it. He’s written a book Metaphysics, but that is tough reading.
I don’t have a good book on the history of political philosophy handy. Reading Hobbes, Locke, Rousseau, Mill should give you a lot of the background, though. Classical (i.e. Greek) political philosophy is too specialized for your purposes; Alisdair Macintyre does explain bits of it, though.
If you’ve finished the list of primary works, and read some of the secondary works, you should know roughly what most of these philosophers are up to, and be able to read contemporary philosophy.
Again, happy reading!