First of all, Biff genuinely wished to pursue his true passions and to avoid wasting the life he recognized as precious. “I’ve always made a point of not wasting my life,” he says, “But all I’ve done is waste it.” Near the beginning of the play when Biff is talking to Happy in their room, he tells him that he’d rather be outside with no shirt on his back, working with his hands. He then offers Happy to come with him to the West to start a ranch together—since Happy had been agreeing with him about preferring to work physically, outside in the open air. However, Happy begins talking about showing other people that “they’re made of something,” and becomes wrapped up in prestige over happiness. Biff honestly wants to go after something he legitimately enjoys, and therefore has a glimpse of what perhaps the American Dream truly means, and how one goes about the pursuit of happiness—rath...
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...t of a pleaser when it comes to his family—he sincerely wishes to be accepted by his family, to please them, and to meet their expectations. Often, caring about people, taking things personally, having skewed expectations of them, and wanting too deeply to please them simply to please them can lead to more corrosive and unsteady relationships than even that of hatred.
Intrinsically, Biff held honest intentions and wanted to pursue his own passions, taking advantage of his life. However, he allowed those closest to him to give him too much advice on what he should do even if they did not know for themselves. Therefore, since he had great potential and allowed his own emotions and other’s expectations to too greatly influence the course of his life, and especially since he could admit that he had messed up, he is the most pitiable and relatable character of the play.
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