For me, it's a tossup between "Wreck of the Edmund Fitzgerald" and "Canadian Railroad Trilogy." Both of these tell great tales of courage, suffering and sacrifice. However, if forced to a choice, it would be "Canadian Railroad Trilogy."
You see, this song is especially meaningful to me because my ancestors were all Canadians and most of them were railroaders. My great-great-grandfather, great-grandfather, grandfather and several uncles were railroaders -- some on the Canadian National and others on the Canadian Pacific. As a child, I remember taking the train to go see Grandma and Grandpa in Gananoque (Ont.) in the late 1940's and early 1950's. Grandpa, who had retired as an engineer from the Canadian National, had lots of stories and old pictures that could keep a small boy fascinated for hours on end. Plus, this was when steam locomotives were still in operation and he'd take me down to the roundhouse to see the smoking giants. Years later, I too would become involved with railroading, and even lived out a boyhood dream by actually getting to run a train!
So, for me, Gordon's story of the great undertaking in the 1880's that resulted in the trans-Canada railroad is with a doubt the best of the many stories he has told through song and verse.
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