Cynicism and Idealism are a classic yin and yang, a contradictory pair where we all seem to need both sides. Few of us can really stomach an entirely cynical or entirely idealistic frame of mind. Yet instead of finding some peaceful balance, these polar views seem to eternally struggle for our sympathy.
This struggle is not entirely symmetric:
Let us first notice some patterns about cynical moods. The young tend to be more idealistic, while the old are more cynical. People can remain idealistic their entire lives about social institutions that they know little about, but those who know an institution well tend to be more cynical. Leaders and the successful in an area tend to be less cynical than underlings and failures in that area. Things said in public tend to be less cynical than things said in private. People prefer the young to be idealistic, and discourage the teaching cynicism to the young. Cynicism is not considered an attractive feature.
If you wander a library you will find far more coherent and articulate book-length presentations of idealistic views than of cynical views. Books on education, medicine, government, charity, religion, technology, travel, relationships, etc. mostly present relatively idealistic views, though of course no view is entirely one way or the other. So one reason the young tend to be idealistic is that most reading material they can easily find and understand is idealistic.
This seems to be the way society wants it; idealistic kids make a better impression so most folks want their kids taught that way. But I would prefer a fairer fight between idealistic and cynical views; I'd prefer that kids could easily find and understand coherent and articulate book-length direct presentations of cynical views. I've even considered writing something on this myself. So let me collect the wisdom of our readers: what is the best stuff out there now?
"A people's history of the United States" by Howard Zinn
Several of Sowell's books, including Basic Economics. Some of Hayek's writing is also cynical of ideas like socialism and "meritocracy."