This dissertation looks at the dialectical relationship between Persian literary works representing or alluding to the pre-Islamic legacy and the political conditions of Iran. Through discursive analyses, it shows that these works in new political conditions change the orientation and main thrust of their message, and use or allude to the same pre-Islamic legacy for promoting modernization, criticizing official policies or showing resistance to the ruling establishment. The main thrust of their arguments also subtly indicates the country's future intellectual and political orientation.A transition from the traditional to modern use of antiquity took place during the second half of the nineteenth century, mainly as a result of increased interaction with Europe. Until the fall of the Qajarids, the Persian intellectuals and writers such as Akhundzadah, Dihkhuda used pre-Islamic legacy to support their arguments for modernization. Later, the despotic Pahlavi rulers (1925-79) sought to modernize the country but stifled the democratic evolution of polity and employed the pre-Islamic Persian heritage to strengthen monarchy. Hence, the Persian fiction writers such as Hidayat, Shahani, Danishwar dissociated themselves from official nationalism and used pre-Islamic heritage in non-glorifying ways to criticize the official policies.After the Islamic Revolution in 1979, the new rulers reversed the Pahlavi official policy of glorifying the pre-Islamic Iran, and projected Shi'i Islam as the central element of Iranian identity. In their efforts to create Islamic subjects, they deprived people many of their civil and political rights. In the new political environment, the fiction writers such as Danishwar, Sadiqi and Arian showed remarkable interest in using pre-Islamic mythological and historical references, themes and events in their writings. Such literary production functioned as a literary resistance to the policies of the Islamist rulers.To substantiate the findings about the use of pre-Islamic legacy in modern Persian literature, the dissertation also examined the representation of Iranian antiquity in Persian films. The dissertation showed that the political representation of pre-Islamic heritage in Persian literature finds a parallel, though less pronounced, in Persian films too.