Great question and I had to take a bit of time to ponder it fully.
The Jim song that has most meaning to me is Anything For Love, because that's the song that was playing when Mini-Pud (who's middle name is James btw) was born.
Surf's Up has special meaning because it was the first song I played in the Hotel room after I proposed to my wife on the beach in Tenerife under a full moon.
