A Clockwork Orange, Anthony Burgess
This is... quite the book. It manages to be both more disturbing and far more intelligent than I anticipated.
It's quite an achievement. For one thing, it does a better job of making the reader complicit in the actions of the anti-hero than any book I remember. NADSAT has a lot to do with that, I think- the reader starts out too absorbed in the language to pass judgment on the actions until they are well and truly entangled. In any case, the reader ends up truly allied with Alex, despite his incredibly disturbing refusal to acknowledge any guilt or even sympathy, even meeting the husband of the woman he raped.
The form of it is impressive too, with an unbelievably neat ABA form and a final chapter that echoes, emphasizes, and breaks free of that all at once.
But you don't read it just for the technical accomplishment. Burgess' obsession with free will is thematically fascinating. Even more that the repeated observation/assertion that free choice is more valuable than enforced good, is the problem of determining when a human truly is exercising that free choice. Alex thinks he chooses violence by free will, and yet several places seem to indicate that his violence is just as much of an unchosen, conditioned response as the nausea ever was. And what is up with his image of youth? Does he really believe that youth is naturally conditioned, without ability to exercise choice, and will automatically turn to evil if their environment pushes them that way? It doesn't work for me. (Also, Alex chose the treatment. The fact that he didn't think it would work is irrelevant. Does one not have the ability to freely chose to give up free will?)
Finally, the politics of the novel are fascinating. It condemns the capitalist middle class and communist government in about equal measure, and everything about his world seems designed to imply that the two systems are not far apart at all. Is he really saying that middle class conformity is the same kind of barrier to free will that communist government is? Similarly, the two parties use Alex in almost identical ways for their own ends- the only difference is how
open they are about it, and which ones match his own desires. It's a deeply politically cynical novel.