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Death of a Salesman was first published in 1949. In creating the character of Willy Loman, Arthur Miller aimed to mirror one of the everyday "characters" of Post WWII American society. In fact, one of the models for Willy was Miller's own uncle, who belonged to this generation and was, indeed, a salesman. The behaviors that Miller witnessed, as well as the many stories regarding early American economy framed the historical context of Death of a Salesman.
This time in history, post World War II America, is significant because it marked the first time that Americans began to feel a sense of ownership and pride. This ownership feeling came from the surplus of goods and services that came as a result of the War, bringing tremendous opportunities for businesses, as well as many subsequent schemes for quick cash. Big corporations "ate up" the smaller business owners, and an overall sense of having "more", "bigger", and "better" began to permeate the psyche of society.
In Death of a Salesman, Miller effectively brings through Willy's consistent anxiety to keep up with these powerful trends of his time: his main ambition, hence, is to be able to "catch up" with this fast-paced and cutthroat new world of "make or break". We find this in the many instances when Willy seems to be running a never ending race in place ensuring that he and his family can face up to, and perhaps even surpass, the successes of his neighbor Charley, and his son Bernard. Considering that Willy's generation also lived through the Great Depression, it is no surprise that this new-found "land of plenty" would make men like Willy to become highly influenced by this trend of succeeding fast and "making it" in life. The tragic flaw of Willy's character, however, is that his own weaknesses as a man are the factors that lead him to failure.
Willy Loman's character shows traits that reflect what David Reisman (1950) calls in his book The Lonely Crowd as the "other-directed Post War syndrome". This was a tendency in post-war behavior, according to Reisman, where people apparently had to re-define themselves as citizens of a completely changed society. As a result, rather than looking inside themselves for identity, men, such as Willy, looked at the perception that other's had of themselves. This is the biggest of Willy's tragic flaws: he bestows this ridiculous idea of being "well-liked" as a way to succeed upon his two children.
Since Willy insisted on the twisted idea of achieving success and wealth merely by way of popularity, charm, and charisma, his children learned this canon and bought into it. Biff became Willy's ego-feeder: a high-school insolent jock and bully who bragged about his talent in football. Willy vicariously lived through Biff's successes, and ignored his other son, Happy. As he dragged along, Happy became Biff's shadow and decided to live his life by pretending and lying about mostly everything. Like Willy's own life, both Biff and Happy lead shallow, clueless lives. However, Biff finally wakes up to the facts and lashes against Willy.
I'm not bringing home any prizes any more, and you're going to stop waiting for me to bring them home!
Hence, Willy's ridiculous ambition drags everybody along with him towards a very fake and shallow path. Even Linda knowingly fools herself into pretending to believe Willy's stories. This shows that ambition without technique really leads nowhere.
He is unable to realize his idea of the American dream thus finding himself inadequate and disappointing. When we experience the frustration of our expectation defence mechanisms are triggered in order to protect our egos. Those mechanisms can be mature or immature, his response is unhealthy denial which after years of pent up emotions finally blows up and becomes self-aggression. People around him are influenced by his dark emotions which get worse as the years pass by. Willy chose a profession that was not suited for him and instead of finding something he would excel at he kept to that pipe dream. This realisation came too late, after he had squandered his best years trying tu become a salesman from the beginning (to one to whose funeral many people came).
Willy had set the bar for himself and his sons too high, which ultimately led to him losing his mind and committing suicide when all of his dreams were falling apart. It seems as if Willy regrets not following his brother, and making something big of himself that way, and therefore in his last moments is trying to justify that his choice was just as good and could still make himself and his sons great successes. His oldest boy finds no happiness in his father's career and certainly no talent in it, while his youngest tries hard to live up to his father's standards of success. This leaves his entire family in grief and misery over his lose and their own financial and career failures.
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