Bill tells Willy that "he had the wrong dreams. All, all wrong." ("Requiem")

Willy's quest to realize what he views as the American Dream the "self-made man" who rises out of poverty and becomes rich and famous is a dominant theme in Death of a Salesman. Willy believed wholeheartedly in this treasured national myth, which began during colonial times, and which was further developed during the 19th century by such industry tycoons as Andrew Carnegie and J.D. Rockefeller. In the 1920s, the American Dream was represented by Henry Ford, whose great success in the automotive industry was achieved when he developed the assembly line.

Also in the 1920s, a career in sales was being hailed as a way for a man without training or education to achieve financial success. Pamphlets, lectures, and correspondence courses promoting strategies for improving the skills of salesmen were widely distributed during this decade. These strategies focused on teaching salesmen how to effectively manipulate their clients. Willy would have begun his career as a salesman in the 1920s, when belief that salesmen adept at manipulation and "people skills" were destined for wealth and fame was widespread. However, by the late 1940s, when Death of a Salesman takes place, the job market and prevailing belief has changed, and salesmen (and other workers) required specialized knowledge and training in order to succeed. Because he lacks such knowledge or training, Willy is destined to fail in a business world that demands the ability to play a specific part in a large establishment. Willy, of course, does not realize how things have changed, and he continues to try to strike it rich using his powers of persuasion. Willy's personal representations of the American Dream are his brother Ben and the salesman Dave Singleman, and he views the success of these two men as proof that he can indeed attain the success he is so desperate to achieve According to Willy's version of the American Dream, he is a complete failure.