20 Songs About Hobos

Springtime is here, the economy is in the toilet, you just lost your job (and John Rich is probably going to write a song about it)–doesn’t it just make you want to pack a bandanna on a stick and head out of town on the next freight train? It sure sounds romantic: seeing the country, meeting new people, ditching all your material possessions except what you can carry. Plus, you get a cool hobo name like One Finger Ellis or Seasick Steve.

For the past 150 years, the hobo has been a rich cultural figure for Americans everywhere: after all, we’re a country founded by intrepid, resourceful travelers. And if anything epitomizes that, it’s the hobo. Men like Carl Sandburg and Jack London were hobos, and they’re two of the best writers America has ever known.

But for every Sandburg or London who receives inspiration from roaming, there were a dozen regular guys who got legs chopped off by speeding trains or sliding boxcar doors, suffered beatings from railyard bulls, or contracted some sort of horrible infectious disease thanks to the unhygienic nature of rambling.

If you’re reading this, chances are you aren’t a hobo (unless jungles have gotten high tech since their Depression days). But we hope you enjoy this playlist anyway, even if the only train you’ll ever ride is Amtrak.

• 20. “Gonna Ride a Train” – J.B. Beverley & The Wayward Drifters
  The band’s upcoming sophomore album Watch America Roll By features this excellent song which details a chance meeting between a grizzled hobo chock full of wisdom learned from a life on the road and a down-on-his-luck youngster. Beverley’s no-nonsense vocals combined with badass picking from BanjerDan (aka Dan Mazer) make J.B. and the Wayward Drifters stand out from your average honkytonk band.
• 19. “Nowhere to Sleep” – Chatham County Line
  A man leaves his girl to ramble through greener pastures, but ends up broke and hungry while he spends his evenings trying not to freeze to death. Karma’s a bitch, buddy.
• 18. “Hobo, You Can’t Ride This Train” – Louis Armstrong
  We’re going to have to defer to the philosopher Kristofferson on this one: “If it sounds country, it’s a country song.” And while Mr. Armstrong may be jazz royalty, the subject matter of this one sounds pure country (should you still doubt Armstrong’s country cred, remember that he collaborated with Jimmie Rodgers on “Blue Yodel #9″).
• 17. “Hobo Dreams” – Chris Ledoux
  A middle aged businessman with a three piece suit and fancy office has a chance encounter with a hobo by the railroad tracks and realizes he’s played it safe his entire life. If some smooth-voiced pretty boy sang this one it’d be eyeroll-inducing, but Ledoux’s lived-in baritone makes “Hobo Dreams” a heartbreaker.
• 16. “The Good Life” – Justin Townes Earle
  Earle’s tongue is firmly in cheek as he sings the title track from his first full-length album. This hobo’s got pockets full of jingling change, eats free dinner served out the back door of a fancy restaurant, and gets the occasional Walter Mitty-esque fantasy as he imagines those smiling and snickering at him are doing so with “subtle tones of awe.” What else could a person ask for?
• 15. “Only a Hobo” – Hazel Dickens
  This lyric paints a devastating picture of a hobo whose hard living finally caught up to him: “Does it take much of a man to see his whole life go down/To look upon the world from a hole in the ground/To wait for your future like a horse that’s gone lame/To lie in the gutter and die with no name.” The song was originally written by Bob Dylan, but no one delivers it better than West Virginia’s own Hazel Dickens.
• 14. “Hobo” – The Hackensaw Boys
  After all the bummer songs on the playlist so far, it’s kind of nice to have one that makes hoboing sound kind of fun, what with the wind on your face and the sun on your back. The hobo in this song was faced with choosing between his girl and his desire to ramble. He might be sad, but at he’s free.
• 13. “Box Car Hobo” – Doug Sahm
  This hobo’s been everywhere from New York to Frisco, but when he’s done travelling, all he wants is to get back to Texas, the land of tacos and Shiner Bock. Oh, and some girl who’s waiting at home. Forget all that nonsense; the sweet sounds of Flaco Jimenez’s accordion on “Box Car Hobo” are enough to bring us to the Lone Star State—and keep us there, unlike Sahm’s restless hobo.
• 12. “I’m a Hobo” – J.D. Crowe and the New South
  From 2006 album Lefty’s Old Guitar comes this tale about a boy who leaves home at 16 to hobo and also to sleep with Southern girls. Pretty standard material for a hobo song, except for an oddly indifferent dad who greets his kid’s desire to ramble with “Son you’ll do your own thing/If you wanna ride the rails, this is what you’ve got to do/You’ll be a hobo but that won’t mean a thing.” After a lifetime spent in boxcars, the boy—now a man—has no regrets. Great advice, dad.
• 11. “Hobo Song” – John Prine
  The opening stanza of “Hobo Song” features Prine reminiscing about the sad hobo stories he’s heard “written in the words of dead men’s songs.” Yeah, that pretty much sums up this entire playlist in under ten words.
• 10. “Ramblin’ Reckless Hobo” – Ernest V. Stoneman
  Okay, “rambling hobo” is a little redundant, but we won’t hold it against old Pop Stoneman, who recorded his version in 1928 accompanied by the Sweet Brothers. Folklorist and song collector Alan Lomax dated “Ramblin’ Reckless Hobo” (which also goes by the title “Western Hobo,” “Danville Girl,” and “Wild and Reckless Hobo,” among others) back to circa 1870-1880. Its age and similar lyrics to numerous later hobo tunes might just make this the ur-text of hobo songs.
• 9. “Lift My Jug (Song for Hub Cale)” – William Elliott Whitmore
  Hub Cale was an honest-to-goodness hobo that Iowa native Whitmore first met when he was six years old. Here he pays tribute to Cale, a man born to “ride the rails ’til judgment day.” Sparse plectrum banjo strumming combined with Whitmore’s whiskey-soaked rasp make this the best song you’ve never heard.
• 8. “Hobo Boogie” – Red Foley
  A hobo learns rhythm from the rails and plays a mean piano in exchange for “a sandwich or a quarter.” He tires of places and faces easily, so he and his hobo boogie have to keep moving down the line. Oddly enough, there’s no piano in Foley’s arrangement, but there is a nifty little whistle interlude.
• 7. “Last of the Hobo Kings” – Mary Gauthier
  Gauthier pays tribute to a dying breed here with the story of Steam Train Maury, a real life King of the Hobos who died in 2006 at 89 years old (he started riding the rails at age 14). After hearing Gauthier speak-sing “He knew how his nation was doing by the length of a sidewalk cigarette butt/Born with an aching wanderlust embedded in his gut/Hounded, beaten, laughed at, broke, chased out of every town/With a walking stick scepter and a shredded coffee can crown,” you’ll be mourning Maury’s passing too.
• 6. “Ramblin’ Man” – Hank Williams
  A freight train’s whistle becomes siren song, and when the song’s protagonist hears it, nothing—not even the love of a good woman—can keep him home. Or maybe he’s just a jerk who blames his wanderlust on God’s will. Either way, it’s one of the essential songs in the Hank Williams canon.
• 5. “I Ain’t Got No Home” – Woody Guthrie
  The socialist folkie was a real life hobo, roaming all over the country playing music until Huntington’s Disease ravaged his body at an early age. With estimates of Depression-era hobos numbering in the millions (these numbers include a fair amount of women and children who also hoboed despite the increased threat of violence), we can assume that the words of this song rang sadly true in far too many ears.
• 4. “Waiting for a Train” – Jimmie Rodgers
  “Waiting for a Train” is one of country music’s most covered songs. It’s also one of the saddest, what with the sleeping in the rain and having a heart filled with pain, not to mention an empty pocketbook. Let’s hope Jimmie Rodgers was a little nicer during his railroading days than the brakeman of this song, who slams the boxcar door in a hobo’s face and calls him a bum (hobos work; bums don’t, making this is a pretty nasty insult).
• 3. “Gypsy Lady and the Hobo” – Boxcar Willie
  With a name like Boxcar Willie you know the man had some good hobo songs. The son of a railroad man, Lecil Martin adopted the Boxcar Willie persona after he retired from his first career as an Air Force pilot; you’d probably do the same thing if your folks named you “Lecil.” Here, two rambling hearts find love over stew at a hobo jungle and roam the country together. We can’t wait to see the Tom Hanks/Meg Ryan movie adaptation.
• 2. “King of the Road” – Roger Miller
  This classic is probably the best known song on the playlist; Miller made it famous, but if we tallied up all the artists who’ve covered it, they’d probably fill a passenger train or two. Instantly recognizable from the first few seconds, who can’t help but to snap and sing along when this one comes on the radio? “Third boxcar, midnight train/Destination: Bangor, Maine…”
• 1. “Big Rock Candy Mountain” – Harry McClintock
  Born in 1882, Harry McClintock was the granddaddy of all hobo singers, and “Big Rock Candy Mountain” is the granddaddy of all hobo songs. Dogs with rubber teeth and lakes of stew and whiskey, and cigarette trees must have sounded like paradise to your average hardscrabble hobo. It sounds pretty damn good to us, too.