Contrast Willy's funeral with Dave Singleman's in Death of a Salesman.

Willy describes the funeral of the salesman Dave Singleman, a successful salesman he greatly admires, as large and impressive. As he explains to Howard, hundreds of people came to Dave's funeral, because he was so well liked. Willy contrasts the impact a likable personality had on people in the old days to what he feels is the "cut and dried" lack of personal contact in the business world today. Willy longs for a probably mythic past in which a salesman could rake in easy money just through personality.

Willy's thoughts about the old days of likability being over suggest that he doesn't, at first, expect to be as mourned as Dave Singleman was. Yet, as he comes closer to suicide, Willy increasingly disassociates from reality. He talks himself into suicide so that Biff can get his insurance money in part by fantasizing about how grand his funeral will be. He describes it to the dead Ben, saying,

Ben, that funeral will be massive! They’ll come from Maine, Massachusetts, Vermont, New Hampshire! All the old-timers with the strange license plates—that boy will be thunderstruck, Ben, because he never realized—I am known! Rhode Island, New York, New Jersey—I am known, Ben, and he’ll see it with his eyes once and for all. He’ll see what I am, Ben! He’s in for a shock, that boy!

Willy, in his heart of hearts, wants very badly for Biff to be impressed with him, so much so that he is willing to kill himself for it. Unfortunately, however, only five people show up for his funeral—his family and his neighbor, Charley. As usual, reality does not align with Willy's grandiose fantasies.

One of the most poignant aspects of Arthur Miller’s play is that Willy increasingly feels envious and judges himself as inferior to other people. The deep-seated sense of failure that leads to his suicide haunts him and poisons what should be his closest relationships: his relationship with his sons.

Only Linda seems to understand what eats away at him, as she retains an image of her husband in his more optimistic youth. Even in considering another man’s death, which occurred while Dave was working and far from his family, Willy manages to bring envy into the situation. He thinks not of the sorrow the family felt that they could not be with Dave when he died, but of the surroundings of a train car as luxurious—another material item that Willy does not have. Willy also is alone when he dies, but the decision was his own rather than in the hands of fate, as he deliberately drove into a fatal accident.

Dave Singleman epitomised success in advertising for Willy. He apparently lived the life that Willy hoped to emulate, and the description which Willy gives of him is where the title from the play is taken:

'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 in to Boston'

There is a sad contrast with Willy's death where the stage directions tell us of his dramatic breakdown-

He turns around as if to find his way; sounds, faces, voices seem to be swarming in upon him and he flicks at them, crying,

Just before he drives to his death.

Also, we are told that Dave Singleman's funeral was huge,

'hundreds of salesman and buyers were at his funeral'

whereas Linda asks why there were so few people at Willy's.

We can imagine that the character of 'Singleman' is unique and venerated in his profession, whereas 'Loman' is invisible, inferior and easily forgotten.