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I have just two points to add to the excellent answers above.
First: before I teach "Death of a Salesman," I write this on the board:
I then ask the class what it means? And what does it mean? It's a sales gimmick, a trick with numbers. $14.99 is as close to fifteen dollars as you can get but still suggest fourteen. The salesman who first came up with the idea (probably back in ancient Rome) hit on the essence of selling... the come on, the little white lie. Such little lies, piled up, are at the core of Willy's being and what it means to be a salesman and to fall for your own pitches.
Add to that, Charlie's speech at Willy's funeral; it is a compassionate eulogy to the life and death of a salesman:
CHARLEY: Nobody dast blame this man. You don’t understand: Willy was a salesman. And for a salesman, there is no rock bottom to the life. He don’t put a bolt to a nut, he don’t tell you the law or give you medicine. He’s man way out there in the blue, riding on a smile and a Shoeshine. And when they start not smiling back — that’s an earthquake. And then you get yourself a couple of spots on your hat, and you’re finished. Nobody dast blame this man. A salesman is got to dream, boy. It comes with the territory.
Willy was a salesman who outlived his ability to sell, and it killed him.
There are lots of ways of looking at Willy's job as a salesman in Arthur Miller's play. I say "job" rather than "career" because in the past salesmen have been looked down upon as being uneducated or having little academic or business training - they were sometimes accused of being little more than pedlars of dreams or worse - lies. Their job is to persuade, and they can do that honestly if they truly believe in the product they are selling. But sometimes they become trapped in trying to aapire to the American dream themselves, and find that they are doing less and less honest work, maybe even persuading gullible and vulnerable clients into buying things they don't want,need or can afford. (Think credit crunch and mortgage foreclosures here.)
To flesh out the character, the author could have chosen any one of many professions, but the fact that Willy is a salesman is particularly appropriate for two reasons.
First of all, Willy embodies the "pluck and luck" optimism and go-getter entrepreneur attitude of the 40s and 50s in the United States. His dialogue is full of platitudes which come off almost as sales pitch slogans, even when talking to family members. He is full of aspirations but has no concrete plan of how to reach his goals. Willy thinks that positive thoughts and expectation will conjure success, much as in a magic formula. Willy incarnates the American Everyman in full belief of "the American dream."
The second reason, his job as a salesman is significant is that it is precarious, as apparently Willy counts on new orders and subsequent commissions as his "daily bread." He seems more focused on his social skills and sales tactics than on the viability of the product itself. When sales drop off, Willy's dreams topple over, with no safety net underneath. His failure is even more humiliating and self-depreciating in light of the flagrant success of his brother Ben.
The only other job more ironic would have perhaps been if Willy had been in life insurance, and a salesman at that.
There are several ways in which this is symbolic and significant: First, a salesman is a person who puts him or herself out to the mercy of his or her own talent to convince people to buy what they offer. This means, that a salesman should be a powerful, enthralling, convincing, magnetic, and enforcing. This, Willie Loman was...once.
Willie, having lost all these qualities gives the reader the exact picture of who Willie is now, and gives us an schema of what his intellectual power is at this point.
Another significance is that a salesman is also a person who cannot be thought of as a solid foundation to support a home. A salesman is way too dependent on circumstances, making him a very vulnerable and, in the end, breakable person. So was Willie. His life became a consequence of his decisions, and of the choices he made in moments of weakness and this is why, in the end, he only had memories to live by, and lots of things to feel sorry for.
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