The Reading Room
Public domain
The Republic
This is where the conversation starts, and in a sense it has never moved on. Plato asks who should rule and answers, uncomfortably, that it should be those who know best, not those the crowd happens to prefer. The argument against democracy is here in its sharpest form, made by a man who watched his own city put Socrates to death by vote. You do not have to agree with him. You do have to answer him, and the answering is most of political philosophy ever since.
The author
Plato
The Athenian who turned the spoken argument into written philosophy, and who built nearly all of it around one question: who should rule, and why. Across the dialogues he writes Socrates as a man asking questions in the street, but the questions do not stay in the street. They become the foundation of political thought in the West. To read Plato is to find that the oldest objections to democracy were also the sharpest, and that answering them is still part of the work.