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One Slovenian (This train): https://www.youtube.com/watch?v=RHtQ4ZF2rGQ
It sings about returning home with a train and how this train will leave without author and how author has enough of traveling.
Gambler from Kenny Rogers is also happening on a train, but is not about trains: https://www.youtube.com/watch?v=7hx4gdlfamo
princess of the night by Saxon (I think) it's my favorite one
Train, Train by Blackfoot is kinda awesome.
Cowboy Troy - I Play Chicken With the Train
I'm also not sure we can leave out the Grateful Dead's Casey Jones.
Does Midnight Train to Georgia count?
Morningtown Ride
Does Journey’s “Don’t Stop Believing” count? Opens with a verse about taking trains!
They did take a midnight train going anywhere.
Peace Train by Cat Stevens
Love Train O‘Jays
Last Train to London by ELO
Chattanooga Choo Choo Glen Miller/ Andrews Sisters
Take The A Train Duke Ellington
Midnight Train to Georgia Gladys and Pips
The sandman, the brakeman, and me by Monsters of Folk
They're a super group of Conor Oberst (Bright Eyes), M Ward, and Jim James (My Morning Jacket). They only did one album, but it's brilliant.
There are about a zillion of them. "I've Been Working On The Railroad" is the most famous I'm sure.
My favorite is Marty Burke's version of "Fast Freight" by Terry Gilkyson. I couldn't find it on youtube but here's Terry Gilkyson's daughter Eliza's version (much different in feel from Marty Burke's version): https://www.youtube.com/watch?v=Sin3FeAQAws (fixed link, had Kingston Trio version earlier, oops).
Added: Found Marty Burke's version! It's been so long since I've heard this!! https://www.youtube.com/watch?v=G8y2iIzk6dw&t=1336s
"Riding On The City of New Orleans" is another one. I mostly know it from a version with rewritten lyrics inspired by James Blish's science fiction series "Cities in Flight". New Orleans, the city, is literally launched into space.
I thought of "America" by Simon and Garfunkel but it turns out to be about a bus ride rather than a train ride. Oops.
Your friend should see the movie "Mystery Train". It's great. Also read the short story "The Hell-bound Train" by Robert Bloch. We need a song based on the Robert Bloch story, which won the Hugo Award for Best Short Story of 1958.
Added: aha! The Bloch story was inspired by an actual song from 1910 (https://balladindex.org/Ballads/R599.html)! Here's a version by Dick Flood (https://www.youtube.com/watch?v=L85ciHPwDf8) and none other than Chuck Berry did a version titled "Downbound Train" (https://www.youtube.com/watch?v=4zCWJNILXUg), maybe because Berry's label wouldn't let him say "hell".
Here's a half hour podcast of a spoken-word reading of the Bloch story. You might want to skip the first two minutes, which are the podcast intro: https://archive.org/download/MindWebs_201410/046TheHell-boundTrain-RobertBloch.mp3
A now deceased friend of mine wrote a parody of "Song of the Shield Wall" about the history of the NYC subway system, but I don't think it's online anywhere.
Here's Leslie Fish (RIP)'s "Grain Train", based partly on her experiences as a railroad yard worker: https://www.youtube.com/watch?v=cRvJ2xgHt0E
Casey Jones? Out there somewhere, I'm sure you can find it.
Peter, Paul, and Mary, "500 Miles".
Oh how could I forget "Charlie on the M.T.A.". A classic. https://potrzebie.review/charlie.html
Tom Lehrer, "The Subway Song": https://www.youtube.com/watch?v=eQKA8UUH2yI
Dubliners' version of "Paddy on the Railway": https://www.youtube.com/watch?v=4kh_O2eyfX4 Again I prefer Marty Burke's version, which starts out livelier. Added: Found that too! https://www.youtube.com/watch?v=YnKjP5cywpo part of a 3-song "Canadian Railroad Trilogy". Someone has uploaded all the tapes of his that I lost decades ago!
Oh this one's important. You're bringing back so many memories. Shadows on a Dime by Ferron, title track of an absolutely intense folk album from 1984. https://www.youtube.com/watch?v=hMvnfBwv_l4
Bob Dylan's album "Blood on the Tracks" sadly doesn't contain any train songs as far as I know.
I'm not that big a train buff but I can understand the wish for a playlist. We almost need a genre of "train shanties" to go along with sea shanties. Sure, ping me with a list!
Added: aha, there is a Wikipedia category. That sort of spoils the fun, but: https://en.wikipedia.org/wiki/Category:Songs_about_trains
Ok, memory jogs from that category. Locomotive Breath by Jethro Tull is great. The category mentions Railroad Bill but the version I'm familiar with is Andy Breckman's. It's funny as hell but barely mentions trains: https://www.youtube.com/watch?v=msAuWlPZuAY
This has been fun!
A few you might not have heard
Two feet ahead of the train - Michael McNevin
And I know it's a Christian song but Josh Turner Long Black Train is so good.
Dave Carter & Tracy Grammer - Hey Conductor
The most famouse song about DB by wise guys
I have one German A Cappella song and one German Volkslied from the 1800s.
Runaway Train - Soul Asylum
Two of my favorites:
Blasting Company - Old black Train, this is from the "Over the Garden Wall" soundtrack. Both the soundtrack and show are great. If you like it then also give "Send me a peach" is also a great song.
- Midnight Special - Trad.
- In the Pines / Where Did You Sleep Last Night - Trad.
- The Beeching Report - I Like Trains
- Night Mail - Public Service Broadcasting
- Oh! Mr Porter - George & Thomas Le Brunn
A couple that come to mind that don't seem to be referenced below:
- Long Black Train - Josh Turner Note: Train is a metaphor
- On The Railroad - The Longest Johns Mostly about laying track, but the refrain is "picking up coal and picking up speed, shovel as much as the engine needs."
9 to 5 (morning train) - Sheena Easton
This train is bound for glory
Long black train - Josh Turner
Down by the station
Baby likes to rock it (like a Boogie woogie choo choo train) - The Tractors
I tried to avoid repeats, but I have to say this one again: 500 miles - Peter, Paul, and Mary
More like light rail, but
The opening line is her waiting at a train station:
Juice Newton - Queen Of Hearts
The folk standard, John Henry
Another standard, Chattanooga Choo Choo
Here by The Nicholas Brothers and Dorothy Dandridge
The O'Jays - Love Train, aka the Soul Train intro song
About a proverbial train
Georgio Moroder - Chase, aka the theme from Midnight Express
Any number of songs about hobos https://www.polarityrecords.com/songs-about-hobos.html
What is/was a hobo, you ask?
Train train (appropriate name, but sounds kind of silly by itself) by Blackfoot
"My Trains" by Lemon Demon
THIS IS MY TIME TO SHINE!
Thank you, seveas-train on #ubuntu-offtopic in the prehistory of libera.chat . I love this freaking song.
The City of New Orleans, Blood on the Coal, and Know When to Hold Them.
trains are cool. despise the real ones, love OpenTTD.
Maybe its a bit of a cheat answer, but the only song the comes to mind is I Like Trains by LilDeuceDeuce and Tomska.
Not a cheat answer imo — that was one of the three songs that cropped up randomly for my friend. The inciting incident, if you will
The Locomotion - any version you can find, they all rule M.T.A. - Kingston Trio Last Train to London - ELO Moonlight Express (album) - The Ivory Heart Love Train - The O'Jays
stretches: Takin' Care of Business - BTO ("if your train's on time...) Rydeen - Yellow Magic Orchestra (licensed for the arcade game Super Locomotive. for a rerelease without the license, they wrote a pastiche called "Ryzeen") Detroit Medley - Bruce Springstein (has a part about a train a-comin' that IIRC has never been done on it's own)