The Twenty-Three Best Train Songs Ever Written–Maybe

Below, my list of the best train songs ever written. In America, at least. Scoff at it, hate it, love it, add to it — you’ll probably be right. My list was selected to reflect the incredible variety of musical genres in which train songs have been written. Folk, rock, blues, big band, gospel, show tunes, skiffle, bluegrass, Newgrass — you name it.

Really: outside of the basics — sex, death, love, God, food, dances, and drugs — have so many popular songs ever been written about anything else? Particularly an inanimate mode of transportation? I don’t think so.

1. “Folsom Prison Blues,” by Johnny Cash. Yes, I know it’s about prison. But it also speaks to the heart of how we feel about trains, that pang we feel when we see them taking other people to other places — even if you’re not in prison. It’s immensely visceral: we can hear the train rolling, can hear its whistle. We can see not only free people but rich ones, “in a fancy dinin’ car . . . drinkin’ coffee and smokin’ big cigars.” In the end, “those people keep a-movin’, and that’s what tortures me.” And isn’t that the American lament in a nutshell, whether we’re doing hard time on a murder rap, or a mortgage-and-family?

2. “City of New Orleans,” by Steve Goodman. Popularized by Arlo Guthrie, it’s not only a song about trains, but also a pretty good one about deindustrialization. Try writing that sometime at home.

3. “The Ballad of John Henry.” The classic 1870s “hammer song.” I always liked the Harry Belafonte version, but it’s hard to find a bad one.

4. “Chattanooga Choo Choo,” by Harry Warren (music) and Mack Gordon (words).Yes, there’s that offensive and anachronistic shout-out to a shoeshine “boy” at the beginning. But this swings. And if you don’t believe me, just watch Dorothy Dandridge and the Nicholas Brothers dance and sing it to the Glen Miller Orchestra.

5. “Mystery Train,” by Junior Parker. Originally a blues song. Who hasn’t done a version? Sure, there’s Elvis. But also Clapton, Bob Dylan and Johnny Cash, the Doors, the Dead . . . it translates.

6. “The Midnight Special.” An old, old folk song, the words first written down by Howard Odum in 1905, and first recorded in the 1920s. My favorite version is Leadbelly’s rendition, but Creedence is also great, and then there’s Belafonte’s 1962 cover, which starts with a hard-driving Dylan harmonica riff to start — supposedly the first piece of music Bob ever got recorded. Contrary to popular lore, it does not refer to the Southern Pacific’s Golden Gate Limited; no such train ever ran. It may have been inspired instead by the Missouri Pacific’s Houstonian, which left Houston around midnight and rolled by the Sugar Land penitentiary where Leadbelly was imprisoned. Or the old Chicago and Alton Railroad’s Midnight Special between Chicago and St. Louis (which, as the Gulf, Mobile and Ohio, ran the last, regularly scheduled Pullman sleeping car in 1971.)

7. “The Wreck of the Old 97.” Reportedly, Vernon Delhart made this America’s first million-selling country-music hit, in 1924, although David Graves George, one of the first people to actually reach the wreck site, made a long and dogged fight in court to claim the song was his. (It was in any case set to the music of an older folk favorite, Henry Clay Work’s 1865 “The Ship That Never Returned.”) The song told of the September 27, 1903, crash of the Old 97, a.k.a., “the Fast Mail,” which ran between Monroe, Virginia, and Spencer, North Carolina, and had legendarily never once been late. The train’s engineer, a thirty-three-year-old named Joseph “Steve” Broady, had been ordered to put on speed by his bosses at the Southern Railway, who were concerned about keeping the company’s U.S. Mail contract. The crash occurred when the 97 failed to negotiate a curve on a forty-five-foot-high wooden trestle outside Danville, Virginia. Eleven men died so the mail could get to Spencer on time.

It’s not true, as the song’s lyrics state, that Broady was going 90 miles an hour; this was a lie propagated by the railroad, which tried to blame the crash on its engineer. But it is true that “They found him in the wreck with his hand on the throttle / Scalded to death by the steam.” Most of the mail burned, too — but the Southern Railway unceremoniously rehabilitated the engine and ran it for another thirty-two years. Again, the best cover is Johnny Cash’s, at San Quentin.

8. “This Train Is Bound for Glory.” First recorded in the 1920s, this traditional American gospel song became a hit for the influential gospel and blues singer Sister Rosetta Tharpe in 1939. Probably the most well-known cover, though, was performed by Woody Guthrie. Yet another train song that seems to incorporate the very rhythms of the rails in its chords.

9. “On the Atchison, Topeka, and the Santa Fe,” music by Harry Warren, lyrics by Johnny Mercer. Yes, it’s a show tune. Deal with it. Or more accurately, it’s a movie musical tune, from The Harvey Girls, director George Sidney’s schmaltzy 1946 tribute to the waitresses at the old Harvey Hotel chain, which offered a decent meal and a bed to Western rail travelers for decades. Judy Garland’s performance won an Oscar for best song.

10. “Dixie Flyer,” by Randy Newman. This song from Newman’s immortal 1988 album, Land of Dreams, tells the story of a trip with his mother back home to New Orleans from Los Angeles, while his father was fighting in World War II. Beautifully evocative, right down to the faint bell of a crossing and the sound of a receding train at the very end. And not without Newman’s usual humor. Its best lines were about his uncles drinking rye whiskey from a flask in the backseat of a “great green Hudson”: “Tryin’ do like the gentiles do/ They wanna be gentiles, too!/ Who wouldn’t down there/ Wouldn’t you?”

11. “500 Miles.” No, not the Proclaimers song from that Johnny Depp movie. “500 Miles” — also known as “500 Miles Away from Home” or the “Railroader’s Lament” — was first put together from snippets of old folk songs that the great Hedy West remembered hearing from her family. There’s a famous version Joan Baez sang live in England, but I’d go with Peter, Paul and Mary’s version, or Rosanne Cash’s.

12. “Downbound Train,” by Bruce Springsteen. In which trains serve beautifully as both metaphor for, and reality of, the collapse of working-class America.

13. “Rock Island Line.” The great folk archivist Alan Lomax first captured a recording of this song on an Arkansas prison farm in 1934. Lomax credited it to Kelly Pace, the convict who sang it for him, but it’s almost undoubtedly older than that. Once again, there are kick-ass versions by Leadbelly and Johnny Cash, while Lonnie Donegan released a sped-up version that set off the skiffle craze in England in 1954. The line in question — the Chicago, Rock Island, and Pacific — never got farther west than the Mississippi.

14. “Paddy on the Railway.” A work song, obviously a converted sea chantey, about Irish immigrants building the railroad out to California. Carl Sandburg, who published a version in the anthology The American Songbag, claimed to have found sheet music for it dating to the 1850s. It was first recorded in 1941; my favorite is the rollicking, snarling Wolfe Tones version: “For it’s Paddy do this / And Paddy do that / Without a stocking or cravat / And nothing but an old straw hat / While workin’ on the railway . . .”

15. “Freight Train, Freight Train,” by Elizabeth “Libba” Cotten. An incredible story, Cotton, a black woman, was a left-handed, self-taught guitarist who played bass lines with her fingers and the melody with her thumb. She wrote this song in North Carolina in 1904, when she was eleven. As an adult, she made her way north and put away her guitar, getting married and having children while scraping out a living as a domestic worker. While working in a department store, she helped find a lost child of Pete Seeger’s — and the rest was history. She became part of the folk revival in her sixties, made enough money to buy her family a house, and won a Grammy in 1984. (It was Peter, Paul and Mary who changed “Chestnut Street” to “Bleecker Street” in their version.)

16. “The Ballad of Casey Jones, or, The Brave Engineer.” Another legendary song about a legendary wreck. John Luther “Casey” Jones was filling in for a sick engineer on April 30, 1900, trying to make up time for the Illinois Central’s New Orleans Special out of Memphis. Steaming around a bend near Vaughan, Mississippi, he spotted four cars and the caboose of an overlong train sticking out from a siding. After telling his fireman to jump, Jones clung to the brake, miraculously slowing his train enough so that he was the only one killed. The song was written in tribute by Casey’s friend Wallace Saunders, a black “engine wiper” who sung it to an older folk tune known as “Jimmie Jones.” Within a couple of years it became a vaudeville and concert hall favorite, but Saunders supposedly received only a bottle of gin for his efforts.

17. “Casey Jones,” Jerry Garcia (music), Robert Hunter (words). This might rank higher, if it had anything to do with trains.

18. “Wabash Cannonball,” by J. A. Roff. First set down in 1882, this is probably the only song about a train for which a train was eventually named. There was no Wabash Cannonball; it seems to have been a bit of hobo mythology, maybe about a “death train” carrying souls to the afterlife. In any event, the Carter Family recorded a version as early as 1929, and Roy Acuff another in 1936. It became so popular that the Wabash Railroad fell into line and named its daytime express run from St. Louis to Detroit after the song.

19. “Long Train Running,” by the Doobie Brothers. Lots of fun — trains as a metaphor for the long run of life without life, including specific mentions of the Illinois Central and the Southern Central Freight.

20. “I’ve Been Working on the Railroad.” Come on, it was the first song you sang in kindergarten! The main verses go back to at least 1894, and likely much earlier. The song seems to have been adapted from a minstrel-show favorite. And the whole “Someone’s in the kitchen with Dinah” part that seems like it comes from another tune? It did, originally — one dating back as far as the 1830s, with “Dinah” a generic term for a female slave. Pete Seeger claimed the “Dinah won’t you blow” part was added much later, by college students. Apparently it has become a very popular nursery rhyme in Japan, entitled, much more elegiacally, “The railroad continues forever.”

21. “Last Train to Clarksville,” by Tommy Boyce and Bobby Hart. The first hit single, in 1966, for that marvelous TV mock-up of a rock group, The Monkees. Boyce and Hart, and their band, the Candy Store Prophets, played much of the music on the Monkees albums. There was an after-the-fact attempt by some listeners to assert that “Clarksville” was an effort to sneak an anti-Vietnam song in under the nose of The Man, because Clarksville, Tennessee, is near Fort Campbell, Kentucky, home to the 101st Airborne. Hart even tried to confirm the urban myth, though he also admitted the song’s geographical inspiration was Clarksdale, Arizona, and that he’d been influenced by the chorus of the Beatles’ “Paperback Writer,” which he heard as “Take the last train . . .” O-kay.

22. “Midnight Train to Georgia,” by Jim Weatherly. Originally about a plane. To Houston. Still, fun to sing along with when you’re drunk.

23. “Bringin’ in the Georgia Mail,” by Fred Rose. A late edition to this list, courtesy of Nick Royal, who wrote me a note after reading my Harper’s Magazine feature on trains. Written by Fred Rose to an old country tune and first recorded by bluegrass immortals Lester Flatt and Earl Scruggs, here is Nick’s favorite version, with Sam Bush on mandolin. Thanks, Nick!

Great train songs that didn’t make it because they were mostly about subways and commuter lines: “Take the ‘A’ Train,” “Don’t Sleep in the Subway Darling,” “My Baby Takes the Morning Train,” and “The Man Who Never Returned, or Charlie on the MBTA” — a take-off on the original “Casey Jones” that started as a campaign song in Boston, and became a Kingston Trio hit. Also, my editor bids me to add Tom Waits’s “Downtown Train”:

Great pick — though I have to admit I also like the over-the-top Rod Stewart version:

The Twenty-Three Best Train Songs Ever Written—MaybeSongs with great train references that aren’t really about trains: “Johnny B. Goode,” “Waitin’ For the End of the World,” “American Pie,” “Dirty Old Town,” and the most romantic song ever written, Eric Maschwitz and Jack Strachey’s “These Foolish Things”: “The sigh of midnight trains in empty stations . . .”