Critical reflections on Homer ́s work have been an integral part of Greek philosophy from its very beginning. In ancient Roman philosophy Homer excited the interest of Marcus Tullius Cicero. The aim of the article is to outline Cicero’s reflections on Homer as well as to explore one of the most original Cicero’s interpretations of Homer focusing on the mythological story of Philoctetes, the king of Thessaly. It is shown, how the Roman philosopher used the figure of Philoctetes as an original in- terpretative means to illustrate not only various ethical theories (such as the Stoic conception of virtue or Epicurean conception of pain), but also physical theories (such as Skeptic theory of necessary causes) as well as logical theories and principles (e.g. rejecting the bivalence principle).