Great discussion! I would have to say 'Ticket to Ride' as he and Johnny head off to Windrixville, and of course 'Help!' when he is jumped at the beginning of the story. 'We Can Work it Out' could be illustrative of the waiting in the church and 'Paperback Writer' for the assignment at the end of the story which becomes the novel.
Let's consider "Eleanor Rigby." Not only does it address the loneliness of the person waiting in the church--looking out, it also addresses the concept of people caught up in the lonely existence of a life in which it doesn't seem to matter what choices are made, the reality of life cannot be escaped. "Ahh. Look at all the lonely people. Where do they all come from?"
What about "Fixing a Hole?" To me, that song is about finding out who you are and what is important to you. I think that Ponyboy spends most of the book doing just this. Maybe by the end of the book he truly is able to sing that "I'm right where I belong."
I also think that "The Long and Winding Road" might work. I see it as a statement of staying true to who you are. If you equate the road that leads to "your door" with Ponyboy's path to "staying gold," I think this would really work as a song for him.
Ah, yet another discussion question I could go to town on. : ) I love the suggestions above, but I find it interesting that my mind went in a different direction when first looking at your question. (And, yes, my mind usually tries to go in a romantic direction even if there isn't one available.) Thus, I immediately thought of these lines from "A Hard Day's Night":
It's been a hard day's night, and I've been working like a dog
It's been a hard day's night, I should be sleeping like a log
But when I get home to you I find the things that you do
Will make me feel alright
It just strikes me as being a perfect refrain for Ponyboy with all of the gang violence he sees (and participates in), ... while longing mostly for poetry by Robert Frost and conversation with Cherry Valance. Ponyboy needs something a bit idealistic to take him out of his realistic world of the Greasers vs. Socs. Poor Ponyboy. Perhaps he should sing more.
[And I have to end this post with a bit of a laugh, ... because even though it has NOTHING to do with Ponyboy Curtis, the Beatles DO sing a song called "Dig a Pony." Ha!]
I think that choosing songs by The Beatles will work well with Ponyboy. I don't have a personal problem with "Within You, Without You," but I think that it's a bit too introspective for him and too ethereal. I don't see Ponyboy as being that aloof and the song has a sensibility that is "other worldly." I do like some of the songs off of that album, though. The song, "With a Little Help From My Friends," could be something to consider. The stress on social solidarity would be significant to Ponyboy's association with the Greasers. Consider when he talks about staying "together" and the song becomes even more significant. Another song that might work would be "A Day in the Life" because it speaks of life, living, death, as well as the experiences in each. The totality of such an experience might be applicable to Ponyboy, who emerges with strength from his experiences in the narrative. Finally, I would suggest that the life lessons he learns to be akin to the closing song, "The End." The moral and message of "the love you take is equal to the love you make" might be something that Ponyboy recognizes in his own experiences throughout the story.
Two of us
Thank you for the help. These are all AMAZING points!