I think that, as with so many other things, you had to be there. This song meant a lot to me when I was thirteen years old. About the same time that Peter, Paul, and Mary had the big hit with "Blowing In The Wind". It speaks to the collective post-Depression post-war denial that anything rather bad had just happened or would ever happen again, as long as Senator McCarthy and his ilk were committed to their righteous crusade. Many people who'd grown up in the Dirty Thirties and come of age during WW II in North America were putting themselves, their selves, into little mental and spiritual boxes on purpose--the identical houses are only a very apt symbol. A few people of that generation, like Reynolds and, say, "the Beats", could see this, and so could us kids, which is why we were so eager to become hippies and live in shacks in the woods just as soon as that way of life was invented. And I don't think people in the UK can really understand this song--their experience of the war was too dire. Also Brits don't have the vast tracts of undeveloped land one finds (found) in California, so the scale of the ticky-tackiness is smaller--real estate development in the UK is almost always a matter of RE-development, usually with the local council taking an active interest rather than, as in the States, with a few local concillors simply taking graft.

All that being said, I've had "Little Boxes" on my mp3 player as part of a folk compilation lately and I find it unlistenable for all the reasons MtheGM and others cite. One ought to pity rather than revile the doctors and the lawyers and the business executives.