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.