Willy brings up his memories of Dave Singleman while he is in Howard's office trying to talk his boss into letting him work in the New York area rather than having to cover all of New England. What impressed Willy was that Singleman was eighty-four years old and still successful as a traveling salesman. Willy is using him to suggest that he himself is relatively young at the age of sixty-three, but he is making a bad impression on Howard. If Willy is still full of energy, then why does he want to be taken off the road? Willy sounds like an old-timer by talking about a man who traveled by railroad in the old days when automobiles were a novelty.
Singleman set a bad example for Willy. Specifically, Willy got the idea that he might never have to retire, so he didn't have to worry about the future. He was the kind of man who would be unhappy in retirement. He didn't know anything but selling. He had thought about doing a little gardening but never got around to it until it was too late. A lot of men do not want to retire or even to think about retiring. As Shelly Levine, a salesman, says in David Mamet's play Glengarry Glen Ross, "A man IS his job." So, partly because of Singleman, Willy never planned ahead but just lived from day to day and from roadtrip to roadtrip. There wasn't too much he could have done, but he did meet lots of people on his travels and he might have found ways of making more money by changing to a different company, or even starting his own little business.
The name Singleman suggests several different things. It suggests that he was a single man, a bachelor. He didn't have Willy's responsibilities or expenses. And he never thought about retiring because life on the road was more interesting than sitting alone in some furnished room waiting to die. The name Singleman also suggests that he is a single, unique example of a man who can continue working when he is eighty-four years old. Willy shouldn't have chosen him as a role model. Willy is nearly used up at the age of only sixty-three. Furthermore, Willy only took Singleman's word for it that he had lots of friends and that he was earning a good living. Singleman may have just been getting by. People who live to be eighty-four don't have many friends left. He was dealing with merchants who were half his age, or less. He may have had some bread-and-butter item to peddle which merchants could use but not in big quantities, so he didn't have any competition. The description of Singleman's magnificent funeral was all, literally, in Willy's dreams. Willy probably had more people at his own funeral than Singleman had. Willy had his wife, two sons, and Charley.
It is interesting that the words "death of a salesman" are spoken only once in the play. This is when Willy is talking to Howard about Dave Singleman.
Do you know? when he died--and by the way he died the death of a salesman, in his green velvet slippers in the smoker of the New York, New Haven and Hartford, going into Boston--when he died, hundreds of salesmen and buyers were at his funeral.
Singleman was homeless. He was undoubtedly buried in Boston because that was where he died. If he had died in Philadelphia, he would have been buried in Philadelphia. Willy thinks there is something glamorous and even heroic about being a traveling salesman, but he himself is an example of the grim reality.
Dave Singleman is a salesman with a reputation of nearly-mythical proportions. Of course, Willy would always take things by face-value, so he would have believed every single thing said about this man. One of the things said about Singleman is that, when he was alive, he lived in a hotel room from where he would sell, be successful, well-known, and still make it rich.
Willy sees those qualities as essential to be victorious in life, and this is what sparks his motivation. This is because, to Willy, David Singleman is the American Dream: money, popularity, easy-done deals, and the benefit of having friends everywhere you go.
And when I saw that, I realized that selling was the greatest career a man could want. ’Cause what could be more satisfying than to be able to go, at the age of eighty-four, into twenty or thirty different cities, and pick up a phone, and be remembered and loved and helped by so many different people?
So little is Willy's concept of "self" that he does not even realize that he depends on being liked, in order to feel his own worth. Moreover, he also thinks that things come easy to everybody, and that there is a specific formula that can be followed by anyone and still achieve the same results. He still does not understand that David Singleman followed his own dreams, and that he succeeded by doing what he felt was necessary. Willy is doing the opposite: he is following David Singleman's dreams, and he expects the same results. Since it does not work that way, Willy will end his life, still not well-grounded.
Dave Singleman represented half of the American Dream for Willy, although he thought it was the whole dream. He was wealth, business success and respect - all things that Willy desperately aspired to have yet never acquired. However, 'Singleman' is a telling, rather Dickensian irony of what Willy would still be dreaming of if he had Dave Singleman's life. A family, he wanted to be a great father, and to have boys who made him proud in the sports and business arenas and preferably both. This is why he continually views his fathering experiences with rose tinted glasses and refuses to accept his failings.