This essay descrribes the role of a woman through the prism of classical literature. In classical literature one gets to know about the tough challenges faced by women, as they rarely enjoyed the privilege of equality. Men did not treat women fairly and they could not aspire to become high standing citizens like their male counterparts. The women were answerable to men and did the designated jobs. Their life was mostly restricted to the domestic responsibilities within the four walls of the house and obedience to the commands of men was their watchword. It could be due to the religious injunctions, as interpreted by the wise men of the day. But some authors of classical texts have penned characters showing grit and determination of women and how they fought, to secure a niche for them in the society. Literary works are the reflections relating to the ground-level realities in the society. Many books, such as Giglamesh, Koran, Lysistrata, Jane Austen’s Sense and Sensibility, Henrik Ibsen’s A Doll’s House and Charles Dickens’s Hard Times are discussed in the essay. One can safely conclude that the classical Greek literature provides enough evidence as for the trials and tribulations of the women and their grim conditions. The appropriate term to describe their conditions, in oppression! But the past can not always be judged by assumptions. If the prevailing oppressive conditions in some of the countries are any indication, it is safe to assume that the plight of women then could not have been better.