i think choosing what philosophy to read is a very personal matter, because if you can't really relate to an author or their perspective you probably won't really get into their work. personally, the first philosopher i read was bertrand russell, who i liked at the time for his attacks on christianity and very reasonable, straight-forward, common sense way of looking at things. at this point, though, i think he glosses over most of the genuine problems philosophy faces, and often makes his arguments by calling names rather than really challenge the foundations of his own thought. in that regard, nietzsche is great, simply because he is so confrontational. he is all about challenging your beliefs, rather than forcing you to accept his as true. for nietzsche, "beyond good and evil" is a pretty good place to start, although he assumes you have already read a fair number of people. for understanding the western tradition, descartes and kant are pretty essential, as is Hume, but all three are sort of a drag to read, so you're probably best off getting some sort of anthology that covers them. one of my personal favorite philosophers is chuang tzu (Zhuangzi), a chinese taoist philosopher from the 4th century bc, he is very readable, poetic, and insightful. i also really enjoy the presocratics, you can find pretty much everything that survives of heraclitus' works as about two pages online, and zeno's paradoxes are still... paradoxical. reading plato is useful, but not essential. reading about plato will probably do the same.
getting into more modern stuff, Camus is probably the most accessible existentialist (put off reading Sartre as long as possible) but he's not exactly the most logically rigorous. i personally love Hegel but most people find him incomprehensible and I think you really need to follow Kant through to the end to see where Hegel is coming from. Kierkegaard is a great writer, very poetic, but again hard to relate to for a lot of people. i love Baudrillard, Derrida and Zizek, but they're all operating in their own self-enclosed bubbles high up in the clouds, in a sense responding to the death of philosophy. for a good modern recapitulation of "common sense" philosophy, i would recommend the pragmatists, william james is a pretty good writer, for instance.
some people find bertrand russell's "history of western philosophy" to be a good place to start, but it's huge, and some people will find it incredibly boring. you could always try to look into an issue you're interested in, find a modern philosopher who deals a lot with it, and try to get their most accessible work, since they'll probably deal with the historical-philosophical progression of that idea. i hope you find this useful, good luck!
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