The following paper deals with some of the most prominent aspects of the American Dream through the eyes of three different literary protagonists. The main character of Ham on Rye voices his mistrust towards the concept of upward social mobility amidst the Great Depression, Fear and Loathing in Las Vegas centres around the downfall of the counterculture movement at the beginning of the 1970s and the main character's disillusionment with the Sixties and Zone One deals with racial and social segregation in the 21st century exemplified through a post-apocalyptic setting. The aim of the following thesis is therefore to analyze different periods of social or financial turmoil in order to highlight certain shortcomings of the Dream myth. The protagonists of the first two novels not only express their disenchantment with certain aspects of the Dream, but also hint at its flaws during times of ostensible financial or social progress. The idealized image of the Roaring Twenties is questioned in view of the unenviable position of many disenfranchised groups who did not reap any benefits from the country's general prosperity, while the counterculture movement is criticized in terms of the idea of achieving peace, freedom and a sense of individuality through excessive drug use. The final novel serves as a means of analysing contemporary racial and social segregation in the United States through various periods of crisis, such as 9/11 and Hurricane Katrina.