Willy and Charley are contemporaries, growing up at the same time and in the same place, and even working in the same profession. Though they share this history, they grow into very different people. Charley is a hard-working realist who raises a son who becomes a success. Willy is an entitled dreamer who raises two sons to share his own specific mode of failure - a compulsion to fantasize and a willingness to supplant reality with fantasy.
Looking strictly at the facts, Willy has worked as a salesman for as many years as Charley, and has managed to pay off his house. However, Willy has no capital - moral or financial - to draw upon in his old age. Charley, conversely, has built up his own business and his son has achieved success. Bernard will be in a position to help Charley, should a time come when he needs help.
Willy professes to know about success and about the qualities that lead to success, while Charley chooses not to talk about these big ideas. Instead, he acts. Charley works hard and sees the rewards of that labor, while Willy attempts to find ways to be "well-liked" and fails. Though Willy often berates and belittles Charley, Charley extends a helping hand to Willy.
Charley tries in vain to dispel Willy's delusions and attempts to save him from financial ruin by offering him a job...
Willy's faith in his deluded vision is unshakable. Though Charley attempts to wake Willy up to reality, Willy continues to insist that he is owed something. He claims that his former relationship with his boss, who has been replaced by a son, qualifies him for financial consideration.
Charley attempts to counter this opinion:
"Willy, when're you gonna realize that them things don't mean anything? You named him Howard, but you can't sell that. The only thing you got in this world is what you can sell."
This statement presents a neat summation of the philosophical and personal differences between these two men. Despite the fact that they live in the same neighborhood and have pursued the same profession and watched their children play together, these men exist on opposite sides of an invisible line.
On one side, a dream has failed to come to fruition while a man refused to alter his vision or to compromise. On the other side, a man has grown into a success because he didn't dream, but dealt with reality on its own terms.
Willy and Charley are very different. While Willy has a pathetic need to be loved and liked, Charley on the other hand feels that it’s not of any importance whether a man is liked or not.
Charley is also more successful financially than Willy. Charley owns a business and even offers Willy a job which he arrogantly declines. He also gives Willy 50 dollars per week, as we learn from Linda since Willy’s can no longer sell.
Both men also are very different in bringing up their children. While Willy pushes his sons,Biff and Happy, to follow a particular dream, of being in business, Charley on the other hand tells Willy that he never pushed his son Bernard about what to be. He,Bernard, eventually became a lawyer arguing a “a case in the supreme court".