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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 attributes Biff's former popularity and success to his smile. Now, however, it seems that Biff's smile and good looks just haven't been enough to get him to a stable place in life. Yes, it seems that Biff's attractiveness just hasn't gotten him that far.
WILLY: I’m fat. I’m very—foolish to look at, Linda. I didn’t tell you, but Christmas time I happened to be calling on F.H. Stewarts, and a salesman I know, as I was going in to see the buyer I hear him say something about—walrus. And I—I cracked him right across the face. I won’t take that. I simply will not take that. But they do laugh at me. I know that.
WILLY: I gotta overcome it. I know I gotta overcome it. I’m not dressing to advantage, maybe. (Act 1)
Willy assumes his business problems have to do primarily with his appearance. It doesn't seem to occur to him that his real problem may be that people see right through his flimsy, image-obsessed personality. The play may be pointing out that people of real substance are the ones who get real respect.
WILLY: Yeah. Sing to me. [Linda hums a soft lullaby]. When that team came out- he was the tallest, remember?
LINDA: Oh, yes. And in gold. (Act 2)
Willy and Linda place great importance on Biff's appearance when he was a high school football star, as if that had something to do with his talent. The very fact that he was so attractive made them positive that he would one day be successful.