1. "Straw Dogs" - John Gray
This was the first philosophy book I ever read, around ten years ago.
There wasn't much in here I didn't already believe. What it did do was bolster my sense that whether or not there is a God really matters. John Gray's depiction of the human condition in a naturalistic universe is a bleak one. It's not "cheery atheism". And that struck me as the correct picture of atheism. It struck me that value and meaning were difficult to fit into reality if reality had no God. Nonetheless, I believed atheism at the time. Atheism did not strike me as good news, but I thought it reported the facts.
Here developed a fascination over the basis of value and meaning, and a longing to rest in a world where those features have a home. This longing led me, as a teen, to resent atheism for its truth (as I thought back then) and resent theism for not having a better case for being the truth (as I thought back then).
2. "Refuting Evolution 2" - Jonathan Sarfati
The most controversial book on my list.
During my gap year before university, I began seriously exploring Christianity. I was blown away by this book. It was the first book I had ever read that actually tried to give an intellectually satisfying answer to honest questions I had about Christian belief. Evolution had been my biggest objection but after reading this book, I had serious doubts about evolution's truth.
Indeed, as I eventually became a Christian, I eventually became a creationist. These days I have a lot of agnosticism about these issues and I would probably not endorse even some of the theology of this book but it makes sense to me that I found it so powerful. Quite simply, the picture of creationism I had absorbed through secular culture was grossly naive and simplified. Picking up this book, I expected it to actively denounce science while quoting the Bible and to say things like "dinosaur bones were placed here to test our faith." Instead I received a better education in philosophy of science than I had ever received in my secular school, and I was presented with sophisticated arguments (by layman standards anyway) that sure as hell looked like science.
Whatever I think about its ultimate conclusions, this book taught me the importance of an education in philosophy and worldview for distinguishing what the science reveals from what the scientist tells us it reveals.
3. "Tektonics.org" - James Patrick Holding
Okay, this one isn't actually a book, it's a website, but it deserves a spot.
JP Holding's tektonics.org has had an enourmous role in shaping my thinking not just about 'apologetics' but about a wide range of issues internal to the Christian worldview. My thoughts on the nature of God, humanity, the interaction between them, scripture and much else besides have all been impacted by Holding's work.
Reading his work has done more for my appreciation of good scholarship than my university degree. And his special interest in the cultural background of the New Testament has forever changed the way I read the Bible, making much of it clearer. It has also raised serious questions, for me, about the extent of the Bible's cultural particularity and the possibility of 'objective' knowledge of God. Questions that are going to occupy me for the forseeable future.
4. "Sources of the Self" - Charles Taylor
The most insightful philosophical work I have ever read.
I'm close to calling it a page-turner. It's gripping. Just about everything is discussed here. The human self, the good life, knowledge and rationality, art and beauty, God, science, subjectivity and truth, oh, and like the whole of european history. I leave this book proud to be human - so sensitive to our nobility (and fragility) is Taylor. It's full of tantalising clues - pockets of wisdom articulated enough to entice but just short of the total transparency you can get a controlled grip on. Keeps me coming back to draw from its philosophical well.
5. "Dealing with Doubt"/"The Thomas Factor" - Gary Habermas.
I include both of these books because I read them around the same time and I can't distinguish them much in my memory.
I have experienced an unusually high level of doubt about my Christian beliefs (and other important areas of my life). These two books helped me understand, for the first time, that my doubt had a large emotional drive. They put me on the path to learning about the nature of anxiety - a path which has led to real change and freedom in parts of my life that I once thought were doomed to darkness and frustration. There is much I still struggle with but I have a hope I did not have back when the sources of my doubt were opaque to me.
And in addition to these breakthroughs in my personal life, knowing more about anxiety and doubt has also provided a rich source of insight into the nature of faith/trust, in general but also in God.