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BIFF [deciding]: Lend me ten bucks, will ya? I want to buy some new ties.
HAPPY: I’ll take you to a place I know. Beautiful stuff. Wear one of my stripped shirts tomorrow. (Act 1)
Biff and Happy's emphasis on Biff's appearance distracts them from more relevant reality (the fact that Oliver won't recognize Biff). They've somehow deluded themselves into believing that, if Biff looks good enough, Oliver will start forking over the money – even though he hasn't seen Biff in years.
BIFF: I stole myself out of every good job since high school!
WILLY: And whose fault is that?
BIFF: And I never got anywhere because you blew me so full of hot air I could never stand taking orders from anybody! That’s whose fault it is!
WILLY: I hear that!
LINDA: Don’t, Biff! (Act 2)
Biff recognizes that false pride is a barrier to success. The failures of his life have made it impossible for him to ignore the fact that he's just not as cool as his father always tried to make him believe he was. Where is the line between instilling your children with a good self image and making them too big-headed for their own good?
BIFF [with enthusiasm]: Listen, why don’t you come out West with me?
HAPPY: You and I, heh?
BIFF: Sure, maybe we could buy a ranch. Raise cattle, use our muscles. Men built like we are should be working out in the open. (Act 1)
Happy and Biff fantasize about escape from the city and their lives in the business world. The world of manual labor is a welcome change to the rat race of city life. In the big scheme of things, though, is the life of the working class really any more free?