"Mystery Train" by Elvis Presley
When I first got a collection of songs that Sam Phillips had produced at his Sun Records studio, this song immediately struck me cause it's awesome. I think it conveys the chug-chug freedom of a long-distance train ride, the sense of motion and space as you whip across America. I'm not really sure if the train took his baby, and now he's sad, or if it took his baby, brought her back, and now things are peachy, but at least Elvis hadn't yet succumbed to the suffocating sound of pappity pap pap that money-hungry music execs served up for most of his career.
"The Train from Kansas City" by the Shangri-Las
Things are decidedly bad in this one, cause the train's arrival brings romantic complications. I very much appreciate the clips of a steam-powered locomotive that the poster added to this song.
Apropos of Kansas City, "Kansas City" by Wilbert Harrison.
It's not a train song exactly, but I always make a point of listening to it as we roll into Kansas City station on the Southwest Chief when I'm heading from Chicago to LA. It's usually around 10 pm, and the skyscrapers loom in the distance as I peer out the window and imagine fine lookin' gents strolling around with a fat paycheck in their pockets, waiting to find a lady to spend it on.
"I Often Dream of Trains" by Robyn Hitchcock
Unlike the other songs, wherein characters await trains, this one actually takes place inside the space of the moving cars. The narrator wanders through a shifting dream train, and the song's melody shifts accordingly. I think this would make a splendid lullaby if you wanted to raise a lil' Morrissey or Donovan.
"Tren al sur" by Los Prisioneros
Let's get poppy, train enthusiasts! Honestly, since I'm not a lyrics person so much as a melody person, this song remains untranslated in my mind. I kind of make up sounds that go along with the tune when I'm singing along, like I do with many of the rock en español songs that defined my teenage years. Anyway, I like how the song chugs down at the end.
"Last Train to London" by ELO
A different kind of train, a more commuter-style job, comes up in this song, whose scheduled departure threatens to end some idyllic night in the life of the narrator. And this video really illustrates why we should replace our current unsightly railroads with neon tracks.
"Train in Vain" by The Clash
Is this song even about trains? You should let it soothe your ills nonetheless.