The American dream is interwoven and deeply embedded in every fabric of American life. It has also been the focal point of many novels under the genre of American literature. This dream as I understand it, is associated with rugged individualism, generous enthusiasm and idealism in the pursuit of success, fame, power and glory in their supremely possible ways. It trends from old puritanical American culture, the affirmation that Americans everywhere are a special people, "a city upon a hill" like the old puritans of New England called it, a land and place formulated by divine providence and right to be a beacon of hope, promise and freedom to the rest of the world. The basic tenet of this dream for the puritans was an all inclusive affirmation that everyone should belong and get a chance to be treated fairly and justly; that no insignificant person was ever born and that America should be a land where by sheer dint of hard work, pluck and trust in God, any person, regardless of their background and history, can pursue their life. commitments and avocations devoid of monarchical control, demagoguery and the rigid social and class stratification that once characterized the old world. Through much of the colonial era, the neoclassical to the post- modernist years, this feeling of idealism and cheerfulness about America and Americans has evolved, today adding secular and capitalistic overtures to its propositions, perpetrating a hegemony of class and social privilege. William Fahey in his book F. Scott Fitzgerald and the American Dream, defined the "dream" as it connotes today. For Fahey, this dream involves "a rise from rags to riches, of amassing a great fortune that will assure a life of luxuriant ease, power, and beauty in an ideal world untroubled by care and devoted to everlasting pleasure with nothing to intervene between wish and fulfillment (70)." In my essay I bring into discussion issues arising from the pursuit of this dream by examining the lives of the protagonists of two important American literatures: Sister Carrie by Theodore Dreiser and The Great Gatsby by F.