I don't know the song and don't know the A train, so, for me this is not more than a common b&w photo.
I have tried to capture your "trick" - if you don't like it I will remove the edited photo.
Nostalgia (it is good thinking: a song from the '30s and this train from the '60s) is much more than just a black-and-white conversion, because nostalgia is memories, sentiment, mood, feelings.
Visualizing a feeling or mood is not easy, don't make things too difficult, when you have to explain a photo from A - Z this normally means it's not an okay photo.
I cut of a piece on the right (a woman standing in the back) and left, put in a zoom blur, a brownish tone and an small amount of noise.