I'm not much of a train guy. Never got that "romance" thing that so many guys see in them. Part of it might be that I don't have much experience with trains. I've seen freight trains all of my life but, have very little experience riding them. A couple of times on the Durango-Silverton, and about a month riding trains around Europe, pretty much sums it up. (I do have fond memories of the ride down the Rhine valley though.) On the other hand, I've lived in towns bisected by tracks. Nothing like getting stuck for half an hour watching a train go by a 1/4 mile per hour to make you hate the damn things.
So why this song then? Partly because of the melody, which I think is just about perfect, especially the chorus. The lyrics really make this song though. "Dealing cards with the old men in the club car. Penny a point, ain't no one keeping score." Has any one every caught the boredom of long distance travel so well? This song is so good that it can almost make someone like me see the what the train guys see in the them. "And the sons of Pullman porters and the sons of engineers ride their fathers' magic carpets made of steel".
Why Willie? I think he sounds better than Arlo.