It’s been about five years since I debuted my theories about hobo tropes in pop music in this space. Dare I quote myself? I dare:
I was born in the late ‘50s, at which point the Depression was still fresh enough in the popular imagination that many of its tropes were fairly widespread. (I should say here that this post is not about the stock market or economic collapse. It’s about pop music.) Among them was the hobo — the man who rambled from town to town, riding the rails, carrying his belongings in a bandanna on a stick. While they were seen as down on their luck, often drunk, just as often they were portrayed as free spirits that society never got its claws into. …All of which is the long way around to notice that every so often a song will pop up in an oldies mix to remind me of how hard this archetype was sold, especially with regards to women.
The songs I cited in support of my argument were Glen Campbell’s “Gentle on My Mind” and Brook Benton’s “Rainy Night in Georgia.” To a lesser extent, the Allman Brothers’ “Ramblin’ Man” and Roger Miller’s “King of the Road.” And this week I listened to another oldie, and realized there’s another one out there, the Marshall Tucker Band’s “Heard it in a Love Song.” To wit:
I’m the kind of man who likes to get away
Like to start dreaming about tomorrow, today
Never said that I love you, even though it’s so
Where’s that duffle bag of mine? It’s time to go…I’m gonna be leaving at the break of dawn
Wish you could come, but I don’t need no woman tagging along
Always something greener on the other side of that hill
I was born a wrangler and a rounder, and I guess I always will
As we used to say in the features department, three makes a trend. I am now ready to write my masters thesis, “Hobo Tropes in Pop Music and Their Role in Early Third-Wave Feminism.”
Hobos. You never hear about them much anymore. Someone presents with no fixed address and no desire for one, and we think: Fentanyl. Untreated mental illness. Trafficking. Addiction. Supportive housing. SERIAL KILLER. And yet, when I was a kid, the raggedy man who picks up cigar butts to grab a few more puffs out of them (Roger Miller: I smoke old stogies I have found / Short, but not too big around) was almost a comic figure. Kids dressed as hobos for Halloween, with fake dirt rubbed into their cheeks and that aforementioned bandanna on a stick. They must have been commonplace, although I can’t remember ever seeing one, except maybe loitering around an SRO in Columbus way, way back in the day.
Times change.
How was everyone’s weekend? Mine has been amazingly unproductive, and that is fine. Blew most of Saturday on an extended lunch with friends, with drinks, that concluded close to sundown. As we left our last stop, TWO different and unrelated parties of barflies hailed us to praise our jukebox choices. What can I say? Sometimes barroom golf TVs just need a Fleetwood Mac soundtrack.
Today? I’m a teensy bit hungover, and should at least sweep and dust at some point, which I probably should do now. Let’s have a good week, shall we?
Mark P said on February 22, 2026 at 3:29 pm
Today is my wife’s last day at the nursing/rehab facility. I’m not sure how it’s going to work out at home. She has recovered physically but still has noticeable cognitive problems. Yesterday she said she was going to kind of miss the place. She has a lot more interaction with people there than at home. She stops and talks to just about everybody, including those with obvious dementia.
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Dexter Friend said on February 22, 2026 at 5:43 pm
For 4 years I followed Shoestring, a hobo based in Tennessee, on Facebook. He was very happy to see $300 in his monetizing account once in a while. He had a small following. He died a couple years back, drowned right outside his Johnson City apartment. His place was decorated with much train memorabilia, but he got antsy quickly and rode trains all over the nation. He made camp, hidden in brush and weeds alongside tracks. Sometimes engineers would throw him a few bottles of water down, some would flip a couple 20s down to him ; he was not adverse to donations. He was legally blind and partially deaf, and when he died he was 51 years old.
I only saw one hobo, about 30 years go on a grainer car. 60, 70 years ago, my friend lived near the NYCentral tracks in Indiana. His mother would always have a pot of soup on the stove, and she baked bread. Word was spread, and occasionally Bethel would hand out a clean tin can of soup and a hunk of bread to any hobo who showed up. Shoestring on YouTube is likely still up. He made great videos. Another guy who made great hobo videos was Stobe the hobo. He was young when he got drunk and was killed by an oncoming train. He was a great pianist and used his own compositions on his videos.
Stobe drank beer like I used to…like damn-nearly constantly.
Santa Rosa is where a large switching yard is. Lots of young people hop-out on trains there, yet today. There are podcasts of parents trying to understand why kids want to travel around so dangerously on freight trains; I listen sometimes. I have worked unloading boxcars and have taken samples of aluminum blocks from freight cars for testing, but never have I ridden the rails in a grainer, gondola, or boxcar. Only coach on Amtrak and years ago on the B&0 and also the NYCentral passenger cars, almost 60 years ago.
And…USA beating Canada in men’s Gold Medal ice hockey made for a great contest, overtime, even. That is all I watched of the entire Olympiad, 2026.
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Sherri said on February 22, 2026 at 6:52 pm
Maybe hobos will make a comeback.
When I start feeling really out of sync with what I see going on around me, I try to learn more to see if I’m crazy. All the AI hype has me feeling particularly crazy these days, so I’ve been trying to get a handle on understanding more about the investment in it.
To me, it seems like absurdly crazy amounts of money are being spent on AI, so much so that it doesn’t seem possible that a return on that investment could ever be possible. So, I tried to look at other pieces in the sky big investments that show no sign of providing return any time soon. How much, I wondered, has been invested in autonomous vehicles so far? From what I’ve been able to find, roughly $50 billion has been invested in this field, with no hope of profitability any time soon.
A lot of money, right? Amazon, Alphabet, Microsoft, Meta, and Oracle have indicated that they expect to spend collectively $500 billion in 2026 on capital expenditures related to AI. A factor of 10 times the total investment in autonomous vehicles in just one year, on top of what’s already been spent, without even any clear idea of what a product that might pay off might look like.
Sometimes, we used to say of a tech, that it was a solution in search of a problem. It’s not clear to me that generative AI has even reached this stage yet, though the hype would have you believe it’s going to utterly transform everything. Right now, it’s like an intern that produces more crap than useful output, and requires careful supervision from an experienced person, and costs way more than they’re worth. the difference is, that human intern is an investment; they are gaining experience and learning from their mistakes, and the hope is they will eventually turn into useful employee. Despite the talk of AI “learning”, that’s not what’s happening with generative AI. The hype would have you believe that early rates of improvement will continue forever, and that’s never true. So-called hallucinations are not going to go away, because they are a function of the probabilistic way the system works. And the harder the companies try to get rid of hallucinations by tuning the training data, the more vulnerable they are to having the training data manipulated (as social media companies discovered in trying to deal with COVID misinformation.)
OpenAI and Anthropic are the two companies driving all this money frenzy, yet neither of them have the revenues to support anything near this level of investment, nor any indication how they’re ever going to achieve those kind of revenues. Their most optimistic revenue numbers now are what are called Annualized Revenue Rate, where you take their best monthly revenue and multiply by 12. Right now, ARR for these companies combined is less than $20 billion, and they’re spending way more than they make. They are likely losing money on every user they have.
Anthropic just closed another round of funding, at $30 billion. Reportedly, OpenAI is rounding up investors for another round of funding looking for $100 billion. There’s talk of IPOs for both companies, because they’re running out of places to raise money in the private markets. I hope they don’t, because the last thing we need are pension funds investing in this stuff. Because it will all come crashing to earth at some point. AI winter always comes. It always has for 70 years, since AI was defined. This time, though, I worry it will take down the global economy with it.
But maybe I’m just crazy.
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Nancy Friedman said on February 22, 2026 at 8:13 pm
Hobos are still around. A journalist acquaintance of mine, Danelle Morton, created a podcast about hobos after her teenage daughter became one. It’s terrific: https://danellemortonwrites.com/podcast/
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annie said on February 22, 2026 at 9:32 pm
to add to your list: Snowin’ on Raton by Townes Van Zandt
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Dave said on February 22, 2026 at 11:50 pm
I remember seeing a few hobos during all my years, I remember talking to one in Bellevue, OH, who had been in a boxcar on a train that I was on. He told me our rail rode surprisingly well, he was expecting much a much worse ride and claimed to have ridden all over on the western roads.
I would walk through the power before we would leave and one evening in Cincinnati, as soon as I stepped into the cab, I knew someone was there. He was an older man, hadn’t been near a shower in several days, asked me if this train was going to Chicago. I told him I wouldn’t be going to Chicago but the train did. I told him, don’t touch anything and if anything happens, I don’t know anything about you. I didn’t tell anyone, not even my conductor, that he was back there, I didn’t tell the crew that got on in Fort Wayne, I never heard anything about it from anyone so I have always assumed that he made it to Chicago.
If I had a teenage daughter hopping trains and riding the rails, I think I would be thoroughly freaked. There aren’t a lot of boxcars anymore and less good safe places to ride and, as Dexter has noted above, those folks sometimes come to a bad end. I wouldn’t be any happier with a son doing it, either, railroads are still dangerous places.
I only recall seeing people riding trains a handful of other times and I was never one to turn them in, including the two teenage boys who got on our train in Hamilton, Ohio, one rainy night, and ended up hollering up at me in the dark at Montpelier, IN, the first place we stopped, asking where we were. They’d gotten on our train in Hamilton, thinking they could have a nice slow ride out nearby their homes but we were going too fast by then and they didn’t dare try to get off. I managed to get them on a train going the other direction without anyone officially finding out and that engineer told me he got them off there.
My wife had two uncles who said they rode trains during the Depression out to California from Ohio, looking for any kind of work. My mother, a Depression child who grew up not far from tracks, said she thought they had her childhood home marked, which they would do, because my grandmother would always give them a little something to eat.
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alex said on February 23, 2026 at 12:06 am
Hobos were still a thing in the popular imagination until fairly recently, at least in Fort Wayne, where we had a locally produced children’s show called “Happy the Hobo” (also known as “Happy the Homo” by those acquainted with the theater queen who served in the starring role.)
“King of the Road” may very well have kicked off the first wave of feminism. Remember “Queen of the House”? https://www.youtube.com/watch?v=8fpuDCQ7Mp0
“Rainy Night in Georgia” used to bring me to tears. It’s in my playlist of all-time favorites.
Even the word “hobo” hadn’t fallen out of fashion or become politically incorrect until not all that long ago. I remember buying some used modernist upholstered furniture from the library only to lament that it “smelled like hobo piss” during periods of high humidity. My ex has those in his man cave and I’ve got new stuff, but they were some cool-looking barrel chairs, even if they never smelled right. “Hobo piss” was just a catch-all term for “funk from thirty years of thousands of butts, 1968-1998.” The blue and chartreuse weave looked great with my mid-mod decor, all things considered.
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Jeff Gill said on February 23, 2026 at 7:29 am
Mark P, the social aspect of such a place is one of the things that makes them tolerable; while my sister & I are not entirely pleased with the memory care facility we finally had to put our mother in, I can say with dementia, the initial transition period was short, and today even if we could find & afford 24 hour in-home care, we’d not do so because the interactions, odd & askew though they might be, with other residents & staff accustomed to oddity, is something we’d be hard pressed to replicate in her house. Four or five social activities (they are tragic events from our point of view, but much anticipated & enjoyed from hers) each day, plus the communal meals — my mother preferred to eat alone & in silence before, and now familiarized with the room, she is overtly happy there. Perhaps in part because she’s largely somewhere in the early 1950s, we think in Lincoln Hall at Easter Illinois University. So when such a placement becomes necessary, the social element is worth keeping in mind. I say this because I know all too well how hard that decision can be even when all indications point towards the necessity of so doing.
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ROGirl said on February 23, 2026 at 9:20 am
One of the original hobo songs. “But when you die and go to heaven there will be no policeman there.”
https://youtu.be/NN_xvE79iXE?si=7hShZkx8RTiT1gst
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Heather said on February 23, 2026 at 11:02 am
I was in Napa this past weekend for my uncle’s 80th and it was lovely to be in the sun for a couple of says. They were having a “cold snap”–it was in the 50s on Saturday. Of course, we Chicagoans had a good laugh at that.
I was so happy for the US men’s hockey team and then my euphoria quickly turned to disgust and disappointment when Kash Patel showed up to party in the locker room and they welcomed him–and then when they laughed on a phone call with Trump when he denigrated the women’s hockey team–who ALSO won gold, and according to some played better than the men. I guess I shouldn’t be surprised.
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Julie Robinson said on February 23, 2026 at 11:46 am
Heather, same temps here so chuckle away but the pool had just gotten warm enough for me so I’m pouting a bit.
Our niece got a job in Napa a couple years back and thinks it’s paradise. Daughter is headed to CA for a conference so gets to visit her next week. She was going to NYC for a few days first but that leg of the trip obviously got cancelled.
I was happy for the hockey players until I saw Patel and then heard Trump offer to send a military plane for going to the White House. Now I’m outraged, but just waiting for the next horrible thing. As one does.
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Sherri said on February 23, 2026 at 4:10 pm
Trump denigrating the women’s hockey team? But he’s so invested in protecting women’s sports!!!
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alex said on February 23, 2026 at 4:19 pm
It appears Tubby is desperately trying to pack the house with Olympians for the State of the Union lest he find himself playing to a mostly empty room. The women’s hockey team declined the invitation and it’s not clear how many if any of the men’s team will take him up on it.
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Deborah said on February 23, 2026 at 4:42 pm
This morning left from Ling Beach, CA airport which is a fantastic place to our stop in Las Vegas on our way to Albuquerque to get back to Santa Fe. I’m not crazy about the airport in Vegas with all the ugly gambling digital machines everywhere. I’ve not seen anyone win during our stop over.
The weather was blustery while we were in Desert Hot Springs but the hot springs soaks were great even in the rain and wind and our drive back on the palms to pines highway was spectacular.
We had a street walking prostitute sighting back in Anaheim not that far from Disneyland which shocked me. We heard that the cops clean them out and then they come back in about 6 months, repeat, repeat, repeat.
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Deborah said on February 23, 2026 at 7:24 pm
Of course I meant Long Beach.
We are finally back in NM after a long travel day.
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Cheez Whiz said on February 23, 2026 at 9:19 pm
There’s probably a few PhD thesises (thesii?) On The American Hobo and several popular books over the decades. America was always about people on the move, looking for a new life or hustle or staying one step ahead of the law. Your classic Hobo looked like Red Skelton’s Freddie the Freeloader, ragged clothes, bindle, cigar and top hat. The plot of the classic Preston Sturgis movie Sullivan’s Travels was a Hollywood director going on the road for experience to direct a movie called Oh Brother Where Art Thou, which sounded a lot like Grapes of Wrath, which also spends some time in a hobo yard following the Joad’s failing fortunes.
You could add Mr Bojangles to your list, though the titular character wasn’t strictly a hobo. Hobos rode the rails, going from town to town, sometimes working, sometimes begging for food from a place with a hobo’s mark identifying a soft touch. Railroad trasportation seemed to be the defining characteristic separating the hobo from the less romantic Bum. Maybe the railroad connection is what drove the mythology of the free-spirit Hobo, always on the move, no strings to hold him down, with their own language and made-up code of hobo honor.
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Jeff Gill said on February 24, 2026 at 6:07 am
May I add “Carefree Highway” by Gordon Lightfoot, 1974, to the neo-hobo roster?
And then there’s the musician as hobo, voiced in 1973 by Bob Seeger’s “Turn the Page”: “But your thoughts will soon be wanderin’ the way they always do /
When you’re ridin’ sixteen hours and there’s nothin’ there to do /
And you don’t feel much like ridin’, you just wish the trip was through.”
Or in 1982 by Jackson Browne with “The Load-Out”: “We gotta drive all night and do the show in Chicago… or Detroit, I don’t know / We do so many shows in a row / And these towns all look the same.”
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Pam H said on February 24, 2026 at 11:59 am
I was listening to The Highwaymen sing Bobbie McGee (written by Kris Kristofferson) “Freedom’s just another word for nothin’ left to lose . . . got Nothin’ if it ain’t free.” That reminds me of hobos. Freedom means a lot of nothing, so hitching rides and begging food is necessary. During the depression the entire country was trained to believe that was just fine. When you have nothing left, just hop a train or a cross country tractor trailer. What rubbish. But I really like the song.
I just knew that tRump would stick his ugly face into the Olympics. He’s no doubt delighted that the US team made the Canadians look bad, in his mind at least. Canada played a great game and almost won. Now my money’s on him glomming onto at least one of the gold medals, cuz that’s the kind of sleaze he is. Also, not surprised he’s ignoring the women’s team, cuz that’s the kind of sleaze he still is.
I was hoping some hockey team members would not fly off to Washington, show a little self respect. We’ll see.
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Dexter Friend said on February 24, 2026 at 1:55 pm
The one hobo I see on Facebook, “Bazz to the Bone” was Britt, Iowa, King of the Hoboes about 7 years ago at the annual Hobo Convention
. He has logged hundreds of hops, and has documented times he found the DPU (distributing power unit) open, where he would find a cache of water bottles, and would ride there as long as possible.
Once Shoestring was riding with a man he had just met. They went into a diner, there was a donation box in plain sight, for a charity case. This guy grabbed the box and ran out. Of course Shoestring was detained for hours before the cops believed his story; he had no idea this other guy was going to rob that little cash box.
The hobo life is rough; once Shoestring found a decomposed female body. More questions by the cops. He knew nothing.
And…I am going to. Always have. Trump on the SOTU. Gotsta , just hafta.
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Sherri said on February 24, 2026 at 4:20 pm
What’s left of the rank and file at the FBI obviously hates Kash Patel, because the leaks are coming fast and furious now. Delays over responding to the Charlie Kirk assassination and the Brown shooting because no FBI jet was available while Patel was using one for personal travel, on top of his very un-FBI-like locker room performance at the Olympics. Maybe he was looking for Nancy Guthrie in the US locker room?
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Sherri said on February 24, 2026 at 7:47 pm
One of the sports columnists Jeff Bezos discarded puts the US men’s hockey team in perspective: https://www.nytimes.com/athletic/7068426/2026/02/24/usa-mens-olympics-hockey-gold-donald-trump/?unlocked_article_code=1.O1A.kAO3.cOPhmjMUtLdC&source=athletic_user_shared_gift_article_copylink&smid=url-share-ta
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