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WILLY: Biff Loman is lost. In the greatest country in the world a young man with such—personal attractiveness, gets lost. And such a hard worker. There’s one thing about Biff—he’s not lazy."
WILLY: [with pity and resolve]: I’ll see him in the morning; I’ll have a nice talk with him. I’ll get him a job selling. He could be big in no time. My God! Remember how they used to follow him around in high school? When he smiled at one of them their faces lit up. When he walked down the street… [He loses himself in reminiscences.] (Act 1)
Willy's reflections suggest complete faith in the notion that popularity and personal attractiveness bring success. The fact that Biff's life hasn't amounted to much, despite the fact that he was so popular in high school, is truly hard for Willy to understand. It just doesn't fit into his idea of the world.
HAPPY: I bet he’d back you. ‘Cause he thought highly of you, Biff. I mean, they all do. You’re well liked, Biff. That’s why I say to come back here, and we both have the apartment. And I’m tellin’ you, Biff, any babe you want… (Act 1)
Happy really is like Willy Jr. Just like his dad, Happy draws a direct link between popularity and success. Also like his dad, Happy is a little loose with the ladies.
WILLY: [stopping the incipient argument, to Happy]: Sure, he’s gotta practice with a regulation ball, doesn’t he? [To Biff] Coach’ll probably congratulate you on your initiative!
BIFF: Oh, he keeps congratulating my initiative all the time, pop.
WILLY: That’s because he likes you. If somebody else took that ball there’d be an uproar. So what’s the report, boys, what’s the report? (Act 1)
Willy elevates being well liked over all virtues when he suggests that Biff can get away with stealing because of his popularity. In the end, Biff's tendency to steal constantly stands in the way of his path to success.