Lolita - Vladimir Nabokov
A serious contender for my favourite book ever, Lolita is pretty thought-provoking. Nabokov is possibly the only author who could make you empathise with a character like poet and pervert Humbert Humbert, who is in some respects a monster. Take away the paedophilia however, and the book can be considered a conventional love story: two people meet, fall in love and everything seems rosy until one falls out of love with the other and they end up fucking each other's lives up.
A Clockwork Orange - Anthony Burgess
When I started reading this I thought "how the fuck am I supposed to read this?!" It's written in a made up futurist dialect of english peppered with slang terms based on russian words. Burgess doesn't even provide a key! But somehow this proved to be much less of an obstacle than I initially thought and I read it in a single day (it's not all that long). It's a brilliantly brutal story.
Catch 22 - Joseph Heller
I haven't read many funnier books than Heller's 1961 masterpiece. It started off as a bit of a slow-burner, as the first half of the book consists of loosely interwoven stories focussing on a wide cast of caricatures, with a pretty slack adherence to chronological order. But in its latter half, the book gets darker and darker and faster and faster, and as Heller ups the pace, the reader can't help but strive to keep up with him.
Oh and a special mention goes out to Graham Greene's short story The Blue Film.
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