There are many books to suggest, both fiction and non-fiction; history and polemic.  Historical fiction is often a superb way to show the actual workings of past societies

The earliest true attempt at democracy was in Athens in the 5th century BCE. and its lifespan was brief, emerging from resistance to tyrants and lasting only a few decades until oligarchies and tyrants regained control. The Peloponnesian War was in large part the struggle between  the Athenian Empire [ democratic, but including both slavery and subjugation of an extended collection of 'allies' for tribute  and resources] versus the Spartan league [ dominated by oligarchies with a feudal basis].  The final result of this long war was to weaken both antagonists and undermine their political systems.  Events in the war's aftermath are described in,  The Trial of Socrates .   I.F. Stone places the writings of Plato in the context of  Plato's and Socrates' support for oligarchy rather than democracy. 

The Roman Republic was a later experiment in the development of democracy, with an elaborate system of balances that worked for a time, but was again unable to respond and adapt to the needs of an expanding empire. Colleen McCullough's Masters of Rome series of novels is the best re-creation of the politics of the last century of the Republic.  While relying on the noblesse oblige of an aristocracy, the Republic also had democratic elements.  Often, as in Athens, democracy was usurped by demagogues.

Venice was the next state to try forms of democracy, and by far the longest lasting, although once again, its constitution was more republican or oligarchical.  Various smaller experiments in city-state communes of medieval Europe followed, including the long struggles against Medici domination in Florence.  [Machiavelli - The Prince ]  The 17th century saw renewed democracy in philosophy and practice, especially in England and the new Dutch Republic.  But it was the 18th century that gave violent birth to the major democratic revolutions in America and France.

Revolutions always need to deal with the ideas of liberty and freedom, but sometimes, these ideas themselves are not mutually understood.  For example, the American revolutionaries from different parts of the colonies had very different concepts of liberty

In Radicalism of the American Revolution, like an earthquake that turns solid ground to jello, Gordon Wood,  tosses out idea after idea that turn established concepts into shambles

More than two centuries later, the American experiment in democracy has degenerated into a plutocracy, in which wealth and power preempt democracy's ideals of equality and freedom [cf Kevin Phillips' Wealth & Democracy or Isaiah Berlin - Twisted Timber of Humanity].  While Phillips gives a depressing history of the decline, and its corruption thru the centuries, Cadillac Desert focuses on perhaps the biggest corrupter of all - the sprawling water projects of the  American West, in which water is diverted at huge cost to grow crops no one needs, all to support giant corporations that threaten to wipe out the family farms that were the rationale for the projects in the first place.  Taken together, these books demonstrate that ideology or the party in power matters little - elections become a charade, masking the control of government by capital and its corporate controllers.  Kim Stanley Robinson examines these transnational corporations in his science fiction Mars Trilogy

From the left George Orwell's analysis of why socialism fails is apt today, especially in re the Tea Party movement

It was easy to laugh at Fascism when we imagined that it was based on hysterical nationalism....  For Socialism is the only real enemy that Fascism has to face. The capitalist-imperialist govern­ments, even though they themselves are about to be plundered, will not fight with any conviction against Fascism as such. Our rulers, those of them who under­stand the issue, would probably prefer to hand over every square inch of the British Empire to Italy, Germany and Japan than to see Socialism triumphant.

The job of the thinking person, therefore, is not to reject Socialism but to make up his mind to humanise it. Once Socialism is in a way to being established, those -who can see through the swindle of " progress" will probably find themselves resisting. In fact, it is their ,special function to do so. In the machine-world they have got to be a sort of permanent opposition, which is not the same thing as being an obstructionist or a traitor. But in this I am speaking of the future. For the moment the only possible course for any decent person, however much of a Tory or an anarchist by temperament, is to work for the establishment of Socialism. Nothing else can save us from the misery of the present or the night­mare of the future. To oppose Socialism now, when twenty million Englishmen are underfed and Fascism has conquered half Europe, is suicidal. It is like starting , a civil war when the Goths are crossing the frontier.

Socialists have a big job ahead of them here. They have got to demonstrate, beyond possibility of doubt, just where the line of cleavage between exploiter and exploited comes. Once again it is a question of sticking to essentials; and the essential point here is that all people with small, insecure incomes are "in the same boat and
ought to be fighting on the same side. Probably we could do with a little less talk about" capitalist" and " proletarian" and a little more about the robbers and the robbed. ... and that Socialism means a fair deal for them as well as for the navvy and the factory-hand.

For more on this peculiar American Empire ..... after the American Century

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