20 Songs About Hobos

Juli Thanki | May 1st, 2009

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.

  • J.B. Beverly & The Wayward Drifters - Watch America Roll By 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.
  • Chatham County Line - Route 23 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.
  • Louis Armstrong - Complete RCA Victor Recordings 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″).
  • Chris LeDoux - Used to Want to Be a Cowboy 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.
  • Justin Townes Earle - The Good Life 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?
  • Hazel Dickens - It's Hard to Tell the Singer From the Song 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.
  • Hackensaw Boys - Look Out 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.
  • Doug Sahm - The Best of Doug Sahm & Friends 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.
  • J.D. Crowe & The New South - Lefty's Old Guitar 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.
  • John Prine - Bruised Orange 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.
  • Ernest Stoneman - The Unsung Father of Country Music 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.
  • William Elliott Whitmore - Ashes to Dust 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.
  • Red Foley - Hillbilly Fever: 24 Greatest Hits 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.
  • Mary Gauthier - Between Daylight and Dark 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.
  • Hank Williams - Gold 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.
  • Woody Guthrie - The Asch Recordings 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.
  • Jimmie Rodgers - The Very Best Of 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).
  • Boxcar Willie - King of the Freight Train 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.
  • Roger Miller - All Time Greatest Hits 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…”
  • Harry McClintock - Haywire Mac 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.
  1. Peter
    May 1, 2009 at 4:14 pm

    Two more:

    Merle Haggard: “I Take a Lot of Pride in What I Am”
    Jimmie Rodgers: “Waiting for a Train”

  2. Razor X
    May 1, 2009 at 4:16 pm

    And “Hobo’s Mediation” by Dolly Parton, Linda Ronstadt and Emmylou Harris

  3. Razor X
    May 1, 2009 at 4:17 pm

    And “Hobo’s Mediation” by Dolly Parton, Linda Ronstadt and Emmylou Harris

    I meant “meditation”, not “mediation”.

  4. Chris N.
    May 1, 2009 at 5:03 pm

    Hobos are great mediators.

  5. Juli
    May 1, 2009 at 5:09 pm

    Peter: “Waiting for a Train” is #4; it just barely edged out “Hobo Bill’s Last Ride.”

  6. Rick
    May 1, 2009 at 5:33 pm

    Juli, choosing between “Waiting for a Train” and “Hobo Bill’s Last Ride” for Jimmie Rodgers’ contribution would be tough. I do think that Iris DeMent’s cover of “Hobo Bill” from the “Songs of Jimmie Rodgers – A Tribute” album from 1997 is hard to beat. In fact that song alone is worth the price of a used copy of that CD and it gets played at the Grand Ole Echo club when I get to be a guest DJ on Sunday afternoons sometimes…

  7. Kim
    May 1, 2009 at 5:48 pm

    had no idea there were this many songs about hobos. thanks for another great list Juli.

  8. Dave
    May 1, 2009 at 5:49 pm

    Any list featuring hobo songs has to have at LEAST one Merle Haggard song.

  9. Rick
    May 1, 2009 at 5:54 pm

    Dave, you’re absolutely right! The main character in “Mama Tried” was a hobo criminal, so how can you beat that! (lol)

  10. Drew
    May 1, 2009 at 6:21 pm

    Not a fan of #1, but good job as usual Juli :)

  11. Drew
    May 1, 2009 at 6:26 pm

    I’m also a little confused as to why there’s a Louis Armstrong picture next to the Chris Ledoux track, lol.

  12. Drew
    May 1, 2009 at 6:27 pm

    Oh never mind, I gotcha, Louis Armstrong is above him, lol, just mixed it up there. Holy, sorry for 3 posts in a row, haha.

  13. Paul W Dennis
    May 1, 2009 at 6:45 pm

    “The Last Ride” by Hank Snow

    “Hobo Bill’s Last Ride”, “Waiting For A Train” and “Hobo’s Meditation” by Jimmie Rodgers, later by Merle Haggard and others

    “Last Train to Heaven” by Boxcar Willie

    “I Take A Lot of Pride in What I Am” – Merle Haggard

  14. Roger
    May 1, 2009 at 9:50 pm

    The Hobo Song on John Prine’s Bruised Orange record

  15. J.R. Journey
    May 2, 2009 at 12:49 am

    You’re the best, Juli. I read everything you write religiously. Great concept here, and a great list. I think Roger Miller should have been #1 though …

  16. JD
    May 2, 2009 at 6:16 am

    “Hobo Jungle” by The Band. Richard Manuel at his best.

  17. bll
    May 2, 2009 at 12:07 pm

    Garth’s ‘Fit for a King’ is a good hobo song.

    I agree with JR- Roger Miller should be #1.

  18. merlefan46
    May 2, 2009 at 7:31 pm

    How about “Trains of Life”

  19. Saving Country Music
    May 3, 2009 at 12:57 pm

    A few I would’ve switched around or added, but a good list nonetheless!

  20. Lee
    May 3, 2009 at 1:38 pm

    I’ve always liked the folkie hobo song, “This Old Mandolin,” by Michael Smith.

    A couple of lines,

    “It’ll play out of tune if there’s a cop on the train…”

    “Before I pass over boy I’ll show you some chords.”

  21. corey
    May 3, 2009 at 8:43 pm

    Great list, but I love Train Travelin’ off of Dierks Bentley first album. Excellent bluegrass song with Del McCoury

  22. Barry M
    May 4, 2009 at 7:40 am

    There are hundreds of songs about hobos–and also by them. There was a book out when Jimmie Rodgers was alive with hundreds collected THEN–though that’s not where he got his from.

  23. TimeO
    May 4, 2009 at 8:23 am

    One of my favorite Johnny Cash songs, though it was never released as a single, is “Crystal Chandeliers and Burgandy,” about hoboing. It’s on his “Junkie and the Juicehead Minus Me” album, as well as the TV special/DVD “Riding the Rails.”

  24. Mike K
    May 4, 2009 at 8:30 am

    Surprised not to see any sky-bo mentions. That’s a new kind of hobo for planes.

  25. diver
    May 5, 2009 at 6:24 pm

    Juli, I have been enchanted by this list. It has led me to do google searchs for all things hobo. What a great list. It reminded me the book , “Water for Elephants”, where the romance as well as the dangers you mentioned of being a hobo are graphically revealed.
    Thanks again for your excellent work,

  26. LizzyH
    May 5, 2009 at 7:50 pm

    I usually just enjoy reading the comments, but had to add to this one!

    A friend gave me a CD awhile back by RANDY KOHRS, a new fav now, and it has a song on it called If All Those Trains Were Still Around (I’d Be An Old Hobo). I think it deserves to be on this list, too!

  27. jg2tn09
    May 7, 2009 at 2:43 pm

    thanks for this article. I can’t wait to check out some of these songs. -jg

  28. Ben Milam
    May 8, 2009 at 3:06 pm

    no mr. bojangles? wtf?

  29. Brady Vercher
    May 8, 2009 at 3:18 pm

    Good suggestion, Ben. It’s one of my favorites.

  30. Mike Parker
    May 8, 2009 at 3:35 pm

    I agree… Mr. Bojangles needs to be there….

  31. Buddynoel
    May 20, 2009 at 1:16 am

    Sorry folks, but if Brook Benton’s “Rainy Night in Georgia” gets left off the hobo list – then something is very wrong with that list.

  32. Duke
    March 14, 2010 at 3:15 pm

    Hobo Bill’s Last Ride is the epitome of a hobo song. Mentioned already in the comments, but bears repeating.

  33. Levi
    March 22, 2010 at 4:45 am

    Woah! Not a mention of Lynyrd Skynyrd’s Railroad Song?

  34. M. Breid
    September 7, 2010 at 10:47 pm

    Has anyone listened to Arkansas Red’s CD Last Train Out? Good songs and stories about hobos.

  35. Skratch
    November 3, 2010 at 2:33 pm

    It’s funny to mention hobo’s wouldn’t be watching this page, but yes technology is amongst us now and people make alot more pay than they did back in the day. i know, i ride trains hitchhike and work occasionally. my man’s in jail some nice people put me up at there house and im using there interweb.

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