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BIFF: Why? You’re making money, aren’t you?
HAPPY [moving about with energy, expressiveness]: All I can do now is wait for the merchandise manager to die. And suppose I get to be merchandise manager? He’s a good friend of mine, and he just built a terrific estate on Long Island. And he lived there about two months and sold it, and now he’s building another one. He can’t enjoy it once it’s finished. And I know that’s just what I’d do. I don’t know what the hell I’m workin’ for. Sometimes I sit in my apartment—all alone. And I think of the rent I’m paying. And it’s crazy. But then, it’s what I always wanted. My own apartment, a car, plenty of women, and still, goddamnit, I’m lonely. (Act 1)
Although he has amassed concrete wealth, it is the intangible aspects of life that Happy craves. Material things and lots of hook ups with random girls just don't seem to be the kind of success that Happy truly wants.
BEN: Principally diamond mines.
LINDA: Diamond mines!
BEN: Yes, my dear. But I‘ve only a few minutes—
WILLY: No! Boys! Boys! [Young Biff and Happy appear]: Listen to this. This is your Uncle Ben, a great man! Tell my boys, Ben!
BEN: Why, boys, when I was seventeen I walked into jungle and when I was twenty-one I walked out. [He laughs] and by God I was rich!
WILLY [To the boys]: You see what I been talking about? The greatest things can happen! (Act 1)
Willy clings to Ben's material success as tangible evidence of his family's worth. He longs to measure up to the financial success of his brother. In many ways, Ben's success fuels Willy's misguided notion that riches are just around the corner.
WILLY: … was rich! That’s just the spirit I want to imbue them with! To walk into a jungle! I was right! I was right! I was right! (Act 1)
Willy interprets Ben's tangible wealth as proof of the worth of his family and himself. He wants his son to be like his brother – unafraid to go out and make their own success.