This paper explores the relationship between philosophy and literature in the dialogues of Cicero. It argues that Cicero was a sceptic Roman philosopher who used the freedom permitted by his epistemological point of view to systematically present the doctrines of all the Hellenistic schools of thought without open polemics in an almost neutral and rather new way. In presenting the doctrines of the different Hellenistic schools of thought, Cicero, on the one hand, devaluates only the philosophy of Epicurus by means of rhetoric. On the other hand, he allows his reader, and even stimulates him, to make a rational choice between different philosophical options such as either the ethics of Stoicism or of the Peripatetic school. To this end, Cicero depicts his fellow citizens and himself in the situation or process of theoretical (and practical) decision-making between different philosophical points of view or even different ways of life.