I would pick different songs from different periods in music to capture much of Phoebe's eclectic and engaging temperament. The first song I would pick would be from The Beatles' last album, "Abbey Road." Harrison's "Here Comes the Song" is probably one of the most intensely poetic and tender songs from the group. Listened in context, it appears right after the song, "I Want You (She's So Heavy)" which is a long and intense ranting type of song, heavy with the group's dabbling in a type of metal. The song is so dreary and intent on moving the listener into a type of other world with its repetition and almost "angry" tone. This is juxtaposed nicely with "Here Comes the Song," a song that emphasizes that after the rain, the sun will emerge. In my mind, this is a great contraposition between Holden and Phoebe, who represents much of the spirit of positive energy and vibrance that Holden is not. This is similar to "Here Comes the Sun" which represents much of "I Want You (She's So Heavy)" could only hope to embody: "Little darling, I feel that ice is slowly melting."
Another song that I would use to represent Phoebe's sense of authenticity and purity would be another Beatles' song, "In My Life." The song is a reverie about the "places and things" that one remembers in one's life. Phoebe's impact on Holden, and how he envisions himself as a "catcher in the rye" and watching over Phoebe while on the merry- go- round would represent the same level of tender reflection that is captured in the song: "In my life, I've loved you more."
In terms of articulating the pain of leaving and the oddly simultaneous feeling of wanting to stay with someone while wanting to leave, The Rolling Stones' song, "Angie," would be a great song that captures both Holden's feeling of wanting to leave, but being doggedly pursued by the feeling of not being able to go. I can imagine this song playing when Phoebe has her suitcase, intending to go along with him: "Ain't it time to say goodbye?"
I have always felt that the relationship between Holden and Phoebe is where the former is troubled water and the latter is willing to be a bridge to happier sentiments and stronger emotional connection. In this light, I sense that Simon and Garfunkel's "Bridge over Troubled Water" speaks quite powerfully to this sentiment. The opening lines could be spoken by Phoebe to Holden: "When you're weary/ feeling small/ when tears are in your eyes/ I'll dry them off." I think Phoebe demonstrates the emotional sensitivity to be that sentimental "bridge" over Holden's troubled waters.