Mediterranean Sea was the passages of interchange of the East and West civilizations, starting with the Orient civilization that spread to Greece. Greek civilization was influenced by the advanced Asian civilization, inasmuch as Roman Civilization was, in turn, heavily influenced by Greek civilization. Terence’s play Brothers in the second century B.C. shows well the conflicts and tensions that originated from the differences in living rural life and urban life of two brothers that took place in Athens. Eventually, the story of the play ends in such a way to connote that Hellenistic values of free-spirited city life supersede the Roman values of diligence and sincerity. In particular, in the end, in Act 5, the strict Demea who lived in rural stubborn surroundings was transformed into a lenient person and won the heart of his younger brother Micio. It is a powerful testament to the Hellenistic influences of the time. By the first century B.C., although the Romans recognized the superiority of Greek culture, they seemed to reveal signs of cultural pride in their Latin culture. De Oratore written by Cicero in B.C. 55 may be considered as an attempt to highlight the features of Roman culture and to introduce an authentic Greek tradition of rhetoric, while emphasizing the practical and realistic elements of Roman characteristics. Furthermore Aeneid by Virgil, the Roman founding epic, is yet an imitation of the two epics Odyssey and Iliad by Homer. We can safely say that it is an ultimate expression of confidence that Romans considered themselves to be destined to rule the Mediterranean including Greece. In conclusion, we can say that Romans accepted Hellenism, Romanized it and then went on to justify the Roman imperialism.