I decided that I hadn't read enough Hugo award winners, and so I started somewhat arbitrarily with the book I'd heard the least about. It also appears to be the Hugo award winner that has been the least reprinted over the years. Originally a serial in Galaxy Magazine, it is very full of "classic" science fiction themes; themes that I most connect with Heinlein, Asimov and even Spider Robinson.
Set "some 40 years after the atomic bomb" it does have a certain alternate history documentary feel today. Here's the alternate history documentary pitch:
Imagine a 1960s in which the "AI Revolution", instead of, as our history witnessed, fizzling beneath it's own monstrous spending and weirder business plans, was quashed for moral reasons; the politicians and populace afraid of anything that sounded like "artificial intelligence", just as today moralists seek to conquer and besiege phrases like "stem cell research" and "abortion". Add to the mix a set of legislative policies collectively known as "opinion control" that force government-approved Fox News-like spin down the throats of the American populace as the only media left standing. The late 1970s and early 1980s that result are then inherently different from the ones we knew. The crippling of the AI Boom and the subsequent stifling of similar techniques kept away the later Personal Computer boom that we saw. Computers remained large, unweildy things locked in the ivory towers of corporations and academia. Then, leave it to academia, when presented with a locked door with neon signs saying "Keep Out" to continue to be secretly fascinated with artificial intelligence. With the right catalyst, an unusual student with the rare gift of telepathy, a university, under a Government grant resembling B. F. Skinner's work for the army no less, sidesteps the "pedestrian' Artificial Intelligence research our own history knows directly, and with little understanding of how it was accomplished, and leaps directly to the "self-aware machine" that we today can continue only to speculate about.
All of the above is mere setting and premise; the backstory to the backstory. The self-aware computer is only a mere lever to the larger question: suppose that immortality were offered to you at the cost of certainty and faith? Would you rather be "right" or would you rather have logic, reason, truth, uncertainty and doubt until eternity? That even means that you have to give up notions of science as you may percieve it for the cold hard reality of not knowing all the answers and not caring one iota. Would you even still be human?
Themes in the novel parallel so much of classic sci-fi: questions of the meaning of humanity, reason, and psychic transcendentalism (a major theme of Spider Robinson's works). It is indeed a well worn classic. At least for me as a fan of classic science fiction I find that it reads nowhere as outdated as it may have been considering the origination (serialized magazine work) and lack of availability. It isn't so much out-dated as it does feel like an alternate history that we as a species are both the wiser and the worse for having missed, and that's something that really speaks to me. Good science fiction for me contains both the distopic and the utopic, the highs and the lows, the good, the bad, the slums, the things we should avoid in our search for a good future and the things we should seek and incubate. I can definitely see why this book won the award, even if it isn't as much of an "all time classic" that speaks to every generation equally.