Western Philosophy is a group of thinkers, problems and attitudes: it divides into three main groups: the pre-Christian, Christian, and post-Christian. There are other traditions, of which an extensive literature has been generated by the Indian, Muslim, Chinese, and Japanese cultures. We're not talking about those book lists.
With that in mind, here's my suggestion.
John Locke's Essay Concerning The Human Understanding. In the same way that modern science starts with Galileo and Newton, modern philosophy starts with Locke and Descartes. The French start with Descartes, the British with Locke.
K R Popper's Conjectures and Refutations. Irascible, insightful, full of himself and full of ideas and learning, Popper was (allegedly) a tyrant in the lecture theatre and a champion of dissent and criticism in his books. This volume covers a wide range of subjects and points to even more.
Aristotle's Nichomachean Ethics. The first encyclopaedic and systematic philosopher, and the inventor of formal logic, Aristotle used to be called The Philosopher by the medieval theologians. His thoughts on personal conduct and the organisation of the State remain relevant. He wrote for aristocrats, but they seemed to need the same lessons the rest of us do. In a modern translation, it is highly readable.
Adam Smith, The Wealth of Nations. Adam Smith was a philosopher who thought about economics. As a result, a lot of what he has to say is still insightful now. You will learn a fair amount about the economic conditions of the time as well, which is no bad thing.
Machiavelli, The Prince. Often thought of as the ultimate Bad Boy of Philosophy, Machiavelli has long since been out-Badded by Saul Alinsky, Rules For Radicals. But reading that made me feel ill.
Montesquieu, The Spirit of the Laws. Influenced by Locke's Two Treatises on Government, modern European political constitutions descend from Montesquieu.
Ludwig Wittgenstein, Philosophical Investigations. Utterly different from anything that came before or since, this is a record of a philosopher working through his thoughts on language, meaning and many other things. I can't think of another book that shows the messy process of almost arriving at conclusions so well.
As accompaniments, add...
...a history of philosophy. The classic is Frederick Copleston's eleven volume(!) set. A more recent one is Anthony Kenny's four-volume A New History of Western Philosophy. I'd suggest ordering one volume of each through your local library and deciding which style you prefer.
...a textbook on Logic. Try Siu-Fan Lee's Logic: A Complete Introduction
...a book or so on the arts of argument and detection of fallacies. Try How to Win Every Argument: The Subtle Art of Controversy by Arthur Schopenhauer, and How to Win Every Argument: The Use and Abuse of Logic by Madsen Pirie
...a book about the use and abuse of statistics.
Some random remarks:
Plato. Yes he was the first to go into print. Yes a lot of his arguments are set-ups. Try it, and if you like it, by all means read more.
The Stoics. Seneca was the Roman equivalent of Jeff Bezos. You're going to take life advice from Jeff Bezos?
Kant. More people read about Kant's ideas, than read Kant's ideas. He's a tough read. One for later.
Hegel and the German Idealists. These guys could not write clearly, and that's being polite. After you have dealt with the idiosyncratic vocabulary, you have to deal with the idiosyncratic ideas. Ones for later.
Heidegger, Merleau-Ponty, Sartre, Jaspers, and the other phenomenologists. Read these guys after you have read the empiricists. Then you will understand the problems they are trying to solve.
Zizek and the cultural theory guys. This isn't strictly philosophy, but if you're in the mood, it can be fun.
Any pop-culture book. No. Just no. These are the equivalent of McDonalds or Mars Bars. Quick hit, no lasting effect. Your brain cells will rot.
Books in series from Routledge (publishers) and others. These can be useful introductions, but tend to present the subject as a neatly-wrapped package of ideas and arguments. What we don't get is the sense of someone thinking about the underlying concepts and problems at first-hand, and that's what we are after.
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