The Wit’s Guide to Hobos

Or, of means by no means

There’s never a return address on hobo mail.

What is it that the hobos have that we working stiffs so desperately crave? Nothing! Well, nothing that can’t be carried in a bindle. Maybe it’s just the bindle we covet? So impractical for carrying a laptop to a cafe, and yet.

“We wander but in the end there is always a certain peace in being what one is, in being that completely. The condemned man has that joy.”
— Ugo Betti

What exactly is a hobo? After the U.S. Civil War, some sizable portion of displaced soldiers decided that the rooted life was not for them. The newly established transcontinental rail service created these boxcar tourists, and subsequent wars and depressions increased their numbers. Then freight trains gave way to tractor trailers and, like dinosaurs into birds, hobos became the #vanlife movement.

“The world is full of willing people. Some willing to work, the rest willing to let them.”
— Robert Frost

But just because you see a fellow riding boxcars across the Great Plains with a polka-dotted bindlestick, doesn’t mean he qualifies. H.L. Mencken set out the rules in 1931: “A hobo or bo is simply a migratory laborer; he may take some longish holidays, but soon or late he returns to work. A tramp never works if it can be avoided; he simply travels. Lower than either is the bum, who neither works nor travels, save when impelled to motion by the police.” Or as David Sedaris explained why hobo was his Halloween costume of choice: “Being at liberty, unencumbered by bills and mortgages, better suited his drinking schedule, and so he found shelter wherever he could, never a bum, but something much less threatening, a figure of merriment, almost.”

“The place in which I’ll fit will not exist until I make it.”
— James Baldwin

Do you own your stuff, or does your stuff own you? While the hobo knows the answer to this trick question, the bank reserves the right to anything valuable, while all the digital entertainments you may think you’ve purchased are actually just long-term rentals. The very first rule of the Hobo Code of 1889 says it plainly: “Decide your own life; don’t let another person run or rule you.” And Rule No. 10 advises against fragrant vagrants: “Try to stay clean, and boil up wherever possible.” A classic hobo is unhoused but well trained, roofless but never ruthless.

“One of the advantages of being poor is that it necessitates the cultivation of the virtues.”
— Jerome K. Jerome

The hobo life required wit because they didn’t have much else. “And of course the whole thing runs on talk, endless talk,” Jeff MacGregor wrote of the last American hobos in Smithsonian magazine in 2019. “Because talk’s free; because even if you give away everything you own, or they take away everything you have, you still have your stories.” And your hobo name, of course. John Hodgman revived the hobo mystique in his 2005 almanac The Areas of my Expertise, which featured an array of hobo codes and 700 made-up hobo names, including Ironbelly Norton, Sammy Austere, and No-Banjo Burns. Compare these to real-life monicas (hoboese for monicker) such as Connecticut Shorty, Jeff the Czech, and Jumpoff John. Then there’s the lingo (Hodgman called it muck-tongue), slang like the jungle (hobo encampments), bone orchard (graveyard), cannonballs (fast trains), and to dog it on the Greyhound bus. Of particular note is the hobo term for a can of beans — “Hundred on a plate” — which is a spiritual ancestor of this great line:

“Rice is great if you’re really hungry and want to eat two thousand of something.”
— Mitch Hedberg

The best hobo phrase has special resonance for Canadians: “It’s a good life if you don’t weaken” was a Tragically Hip song, a Seth graphic novel, and a line from a novel by John Buchan, known to all patriotic schoolchildren as Lord Tweedsmuir, our 15th Governor General. But if you trace it back further, as Garson O’Toole did on his consistently excellent Quote Investigator site, you find it originated in a 1908 newspaper story about a wealthy Utah man who lost a bet and thus had to live as a hobo for 60 days. And guess what? The man of means loved having no means.

“You see,” he told The Salt Lake Evening Telegram, “this jungle life is a grand one if you don’t weaken. Talk about experience, why when I get back to the folks I will have had enough experience to fill a molasses barrel. When I get home I will sure have a bigger heart for these fellows you officers term tramps.”

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“Laziness travels so slowly that poverty soon overtakes him.”
— Benjamin Franklin

For the second week in a row, skylarking was narrowly edged out. The hobos are an irrepressible bunch, but surely August is the time to skylark!

Get Wit Quick No. 318 forgot to mention Stompin’ Tom Connors and Al Purdy, two famous Canadian graduates of Boxcar University. If you’ve ever heard a distant train whistle in the night and thought, I’d better get back to sleep because I’ve got a big presentation tomorrow, the hobo life is not for you. And if your daughter falls in love with a hobo, well, he’s her hobeau. The newsletter mascot is an magpie named Magnus after the magician in Robertson Davies’ Deptford Trilogy. The title font is Vulf Sans, the official typeface of the band Vulfpeck. The book was Elements of Wit: Mastering The Art of Being Interesting. I will neatly collect all the taps of the ❤️ below in my bindle.

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Four quips to distract your therapist