The best train songs tell tales of power, freedom, and fortune as they were once understood by Americans from the California coast to the Georgia pines. At one time, the downtown train depot represented the only way out of town for some. For others, the railroad presented an honest way to make a living. Its mighty locomotives possessed a power only surpassed by a fictitious Superman. The engineer at the helm of the train maintained enough control over this might to suit Biblical analogies of that unseen hand.
And that's just the glamorous side of train songs. Scuzzy hobos, shifty vagrants, and stingy train robbers offered foils for silver screen cowboys and their musical counterparts back when trains remained a vital part of American culture.
Today, these songs represent a different era of transportation and technology. That's not to say they're unrelatable now just because a train ride isn't everyone's main mode of transportation. Leaving on a midnight train doesn't sound like a final goodbye now, but it remains an understandable enough analogy for such lyrics to age well.
This imagery of watching a train drive by appeals to more than just country singers. Folk singers (Woody Guthrie, Pete Seeger, Bob Dylan and Peter, Paul and Mary) and roots-minded rockers and rock bands (Elvis Presley, Bruce Springsteen, The Doobie Brothers, Tom Waits, Lonnie Donegan, the Rolling Stones, and the Grateful Dead) would all contribute to a genre-free list of train songs.
That said, the historic importance of most of the songs that follow capture how a single theme of folk songs and ballads (such as the well-known ballad of John Henry) helped shape the development and commercial growth of country music, bluegrass, and other forms of rural entertainment. Train songs exist outside of country music, but no other genre's development owes more to these stories of the disappearing railroad blues.
With all of that in mind, here's our official playlist of the best songs about trains in the great American country songbook. Note that many of these songs have been covered numerous times. Honorable shout outs to "Midnight Train to Georgia," "Mystery Train," "Long Black Train," "Last Train to Clarksville," "Chattanooga Choo Choo," and "Rock Island Line," and "Midnight Train to Memphis."
10. "This Train," Randy Travis
Sometimes titled "This Train is Bound for Glory," this timeless spiritual song adapted well to country music. Cover versions by Johnny Cash, Hank Snow, and Randy Travis solidified its spot in country music's hymnal.
9. "Trains Make Me Lonesome," George Strait
George Strait helped popularized this late '80s deep cut by Merle's son, Marty Haggard. It beckons back to the time of Jimmie Rodgers while also considering how blues players helped mystify the era of railroad dominance.
8. "Freight Train Boogie," Doc and Merle Watson
This bluegrass corker about Casey Jones best exemplified the varied talent of roots music icons Merle and Doc Watson. Later on, it became one of the more underrated cover songs in Willie Nelson's repertoire.
7. "In the Pines," Bill Monroe
One of the most memorable melodies in old-time music won over fans of everyone from Leadbelly to Nirvana. In the hands of bluegrass innovator Bill Monroe, this gorgeous old tune became yet another example of how trains set the scene in story-songs.
6. "Hobo Heaven," Boxcar Willie
As his stage name suggests, Boxcar Willie built his entire persona around singing great songs about trains. His greatest song reveals that he was more than a gimmick. Willie should rank high on the list of all-time vocal talents, up there with Don Williams and Ronnie Dunn.
5. "Waiting for a Train," Jimmie Rodgers
It'd be just as simple to put together a top 10 list of Jimmie Rodgers train songs. "The Singing Brakeman" sang about the railroads with a voice of experience. He went from a switchman for the Southern Pacific Railroad to the performer on this and other history-altering recordings.
4. "City of New Orleans," Willie Nelson
Chicago Cubs superfan and songwriting great Steve Goodman's story of the Illinois Central Monday morning rail put the fading importance of trains into perspective back in 1971. Willie Nelson later made the song the title track of a 1984 album.
3. "Orange Blossom Special," Flatt & Scruggs
Few songs remain synonymous with bluegrass as "Orange Blossom Special." The longtime measuring stick for fiddle players helped make Lester Flatt and Earl Scruggs household names before inspiring Johnny Cash's classic album of folk standards.
2. "Wabash Cannonball," The Carter Family
The Carter Family's greatest gifts to recorded music include this 1929 reworking of an old tune previously called "The Great Rock Island Route." The band's high-energy retooling shaped the sound of country, bluegrass, and rock music to come.
1. "Folsom Prison Blues," Johnny Cash
Few opening lines in popular music history grab the listener's attention faster. Plus, this train reference points to a creatively bright future for country music more so than a long-lost past for American commerce, making it more important and relatable to modern fans than most other railroad songs.
This story was originally published on June 25, 2020.