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I'm sure any number of songs would explore Willy Loman's character and surrounding effectively. One such song might be Jimi Hendrix's "Castles in the Sand." Of particular interest might be the recurring line, "And so castles made of sand slip into the sea, eventually." In many ways this same idea could apply to the lives of Willy, Linda, Biff, and Happy; their fanciful recollections of the past and their idyllic dreaming of the future will at some point fall apart. The Loman house being surrounded by tall buildings and skyscrappers also mirrors this same line.
This is a great assignment. I would focus on songs that explore the materialist nature of Wily's existence and pursuit of the American Dream. The song, "Money," by Pink Floyd might be one such song. The closing lyrics could have great tie in to Wily's predicament. Dire Straits' classic, "Money For Nothing," and Bruce Springsteen's "Atlantic City" are two songs that explore the condition of materialism in a powerful and vivid manner. Jackson Browne's "Running on Empty" and Bob Seger's "Against The Wind" are wonderful songs that capture the pain at the heart of all endeavor, a pain of nothingness. Wily would be able to identify. Finally, John Lennon's "Mother" is a song about abandonement. While it is about a boy and his mother, one could ask if Biff could sing the same song about Wily's own lack of emotional presence in his own life.
Such good answers! And because they are so good, I will take a look at the question from a different angle.
Rather than make the songs about Willy's situation per se, I would choose songs that are evocative of the era of the play, the 1940s and before. The following choices could be played at certain times during the play... just as it starts, when Willy arrives home, during the numerous flashbacks, in the hotel in Boston, at Frank's Chop House. The songs are melancholy and partly ironic, and will lend a certain authenticity to the specific time and place of "Death of a Salesman."
When You Wish Upon A Star
I'll Never Smile Again
I Ain't Got Nobody
Nobody Knows You When You're Down And Out
U2 has a song called "40" which is about a new beginning. This beginning is spiritual and idealized in a way that relates to Willy and his sense of how life should hew more to the ideal and what falls outside the ideal can/should be ignored.
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