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Perhaps I'll throw out some suggestions. (I'm a philosophy professor, though the kind of philosophy I focus on is not really the kind you tend to read for the “fun” of it.)
Meditations on First Philosophy by Descartes. Far and away the most commonly assigned book into Introductory philosophy classes, since it covers all the basics, and introduces students to rigorous thinking so well (and of course was very influential in its own right).
Three Dialogues Between Hylas and Philonous by George Berkeley (18th century Irish philosopher). This is a beautifully written dialogue in which Berkeley (through the character Philonous) argues for immaterialism, the theory that no matter exists. The arguments are not really convincing in the end, but it may change the way you think nonetheless.
The Problems of Philosophy by Bertrand Russell. This piece is not at all representative of Russell's usual philosophy (for that, look at The Philosophy of Logical Atomism), but it's broader and more accessible, and is a good accessory to the others mentioned.
If you liked Popper, a good next stop would be A. J. Ayer's Language, Truth and Logic, which advances the logical positivist doctrines into more traditional areas of philosophy. These sorts of views are not taken very seriously any more, but in the middle of the century they were all the rage in the English speaking world.
I'd make some more recommendations if people are interested in special topics. E.g., for philosophy of science, read T. Kuhn's The Structure of Scientific Revolutions; for political philosophy, try John Rawls's A Theory of Justice; these are high level works but still accessible.
It's not really my cup of tea, but people interested in existentialism usually start with Sartre's Existentialism is a Humanism (though I think he himself wouldn't regard it a serious work). If you were more into Nietzsche, my favorite work of his is The Genealogy of Morals, though that's not saying much (--don't much care for that kind of stuff.)
I've never heard anything good from a academic philosopher about Simon Critchley's work (and I've read lots of bad stuff), though I haven't read it myself, so take that with a grain of salt.
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