For basic orientation
There are numerous synoptic books on the history of western philosophy. I’d suggest reading at least one of these, to get basic orientation of the canonized western philosophers, and to get a “traditional” view on how to interpret these thinkers. There are several alternatives. One which I think is OK is Bertrand Russell’s History of Western Philosophy. It has the benefit of being written by one of the most famous philosophers of 20th century, who’s no doubt a sharp thinker. Also it exists as audiobook, and large parts of it can be found on YouTube. Just don’t take all what he says for true or great sense. He seems to mess things up when talking about the pragmatists, for example. A great introduction to pragmatism, look at William James’s lecture, “the meaning of pragmatism” http://www.marxists.org/reference/subject/philosophy/works/us/james.htm (also could be downloaded from Librivox http://librivox.org/pragmatism-by-william-james/ (lecture 2)). This is brings a concise and easy-understandable presentation of pragmatism I believe.
Reading Russell’s History of Western Philosophy, you only get the history until early 20th century. Authors such as Wittgenstein and Heidegger aren’t mentioned. (Any tips on synopsis of 20th century philosophy?)
Alternative view on philosophy
For an alternative view on the history of philosophy, I would recommend Richard Rorty. He is well oriented with the history of western philosophy, and brings interesting perspectives which differ from conventional readings. He has a great ability to express difficult matters comprehensible. Most importantly, he dares to be controversial, and challenges the most fundamental conceptions on what philosophy is about, such as claiming there is nothing philosophically interesting in the concept of Truth.
One can object that Rorty is not always fair and neutral, in his depictions of philosophers. There probably lies some truth in this, but more or less this applies to everyone. Richard King points out: “Given his dismissive manner, it is easy to accept Rorty’s conclusions without following his argument, to parrot his assertions without earning the right to do so.” Just as everyone else, Rorty should be read with caution.
One of the texts by Rorty, “Platonists, Positivists, and Pragmatists”, available free on the Internet:
Reading primary literature (by the philosopher) or secondary literature (about the philosopher)?
Think for yourself, who do you think best could describe you? You yourself, a friend/admirer of yours, or a distant person in your class who’ve seen you many times, knows who you are, but not at all a friend or admirer of yours? You probably say you yourself, and as a second choice your friend. However, imagine now that the listener who you are being described to, knows not at all the language that you speak, but can understand the language of the distant person in class. Then we may imagine this distant person in class is after all the one who describes you best, as she at least can say something understandable about you for the listener. In order to understand a philosopher, often the dilemma can be like this, I believe.
Best way to really get to know a philosopher is to read what the philosopher himself writes, but often that will become too hard. Then don’t waste your time. Find your way through the secondary literature instead. Just make sure by some time to actually get down to what the philosopher actually say himself if you’re still interested in him.
Reading the original texts can be very different from reading secondary literature. Take a look at some of Plato’s dialogues, for example, and you’ll probably notice it’s quite different experience from reading about them by academic philosophers. Academicians tend to treat Plato/Socrates as a dry theoretician, but reading the dialogues, you find it’s very much alive, with story-telling and ordinary conversations.