Through the early to mid 1900s, the concept of striving to attain more than one is originally born with became predominant in most American societies. During this era, many authors, through literature, began expressing their concern with the rise in materialistic ideals and its effect on society and the individuals living within it, one being F. Scott Fitzgerald. Two of Fitzgerald’s widely-known works of literature, The Great Gatsby and “Winter Dreams”, both heavily elaborate on the effects of the increase in materialism and the ultimate effects of attempting to achieve the American Dream; this is conveyed through the unhappiness of the Dexter and Gatsby despite their perseverance to acquire women of higher social statuses. These texts both reach the conclusion that the American Dream is not within reach of anyone. Fitzgerald’s representation of the unattainable American Dream is demonstrated in The Great Gatsby and “Winter Dreams” through his portrayal of the materialistic nature of society as well as the characters’ failure to possess the women they love. By portraying both Gatsby and Dexter as taking great lengths to achieve their dreams, but however ultimately failing, Fitzgerald implies that striving for more than what one is given generally results in not only eventual failure, but also a decay in moral values. Both pieces of literature demonstrate the concept that hard work cannot always guarantee success, with success primarily defined as attaining the American