A recent "reply" from Ian Prowse on Twitter has made me think about this. I've always considered Pete Wylie's anthemic "Heart as Big as Liverpool" because the fact that it's anthemic . It is a truly great song regardless of it's connections to Liverpool in it's subject and composer. It should be in everyone's music collection and I think has become ingrained in my Liverpool associations (I worked there on and off for for years). I also love the video and wish there was some way of having a video rotation at the top of this post.
"Does This Train Stop On Merseyside" does take it up a notch. First of all it is a great song, and very simple to play, with a great chorus, but it is also a wonderful four minute history of Liverpool , with references to slavery , locations , the Maryland Pyramid , Hillsborough and much more. It triggers questions in your mind about the city in an excellent way , so much that Ian Prowse and his band Amsterdam actually did a documentary about it.
My favourite rendition is Ian's solo performance in Liverpool cathedral though it was originally released by his band Amsterdam (who , when I first saw them I went and bought their two available albums they were that good) . I am going to share those lyrics here , as well as the documentary and links to buy the music. I think overall Ian Prowse wins this one but you are talking a 9.9 versus a ten, both superb songs.