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Songs appear throughout the novel, most often when Winston is reflecting on the state of the world. Music appears to inspire Winston and allows him to see beauty and simplicity in an otherwise violent, ugly, and frightening world. He sees a powerful sense of tragedy in "Under the spreading Chestnut Tree," hope for a brighter future in the beautiful thrush song, respect for the true, untouchable past in the "St. Clement's Dane" rhyme, and freedom and hope in the passion with which the prole woman sings while hanging her laundry. Below, listed in chronological order are the musical events that occur in the novel.
Winston describes sitting in the Chestnut Tree Cafe, observing the clearly beaten, defeated, and tragically sad Jones, Aaronson and Rutherford, while the song "Under the spreading Chestnut Tree, I sold you and you sold me" plays over the telescreen. The song seems to reflect the broken spirits of these three men, who were once Inner Party members and now have lost everything.
Mr. Charrington teaches Winston the rhyme that begins "Oranges and lemons say the bells of St. Clement's," which is a vestige of the past. Throughout the novel, Winston holds on to this rhyme and tries to discover its entirety. He succeeds, with the help of Julia, who remembers a few more lines than Mr. Charrington, and O'Brien, who finishes the poem for Winston.
Julia and Winston are in the Golden Country, beginning their affair. As they stand next to each other surveying the landscape, a small thrush begins to sing next to them. Winston is taken in by the bird's boundless freedom and wonders what makes him sing so beautifully. To Winston, the bird's song represents all he longs for in life. It is the exact opposite of the Party.
Winston hears the prole woman in the yard behind Mr. Charrington's house sing while she works. She belts out the tune without any hesitation, throwing herself into the simple music with a passion Winston reveres.
Winston tells Julia of the poem Mr. Charrington taught him, and she adds two verses. Her grandfather taught her the rhyme when she was young, and Winston is elated to learn the next few lines of the piece. This cooperation reveals a strong bond between Winston and Julia.
Winston discusses the Hate Song the Party created solely for the Hate Week celebration. This is the only time we hear of a song created purely for negative means. Winston notes that the Hate Song is not as popular among the proles as some of the more simple tunes the Ministry of Truth has produced for them.
O'Brien completes Mr. Charrington's rhyme, and Winston is immensely satisfied to finally know the complete piece. He feels that gaining the last puzzle piece from O'Brien symbolically represents their bond in rebelling against the Party and pursuing a future steeped in freedom.
Winston again hears the prole woman singing passionately while doing her wash and reflects on the primitivism in song. Winston thinks about the millions of people around the world, just like this woman, who find such pleasure, power and freedom in music and are able to embrace it in their lives. He is arrested immediately after this brief scene, which fulfills the last line of the "St. Clement's Dane" song, "Here comes a chopper to chop off your head!"
Winston sits in the Chestnut Tree Cafe, just as Jones, Aaronson and Rutherford once did. He hears the same song he heard when watching those three men, "Under the spreading Chestnut Tree, I sold you and you sold me." Here, the song speaks to the destruction of Winston's independence, and his newly discovered love for Big Brother.