Hobos are either homeless people viewed through an industrial-strength Nostalgia Filter or living Americana: freewheeling folks, usually men, who for any number of reasons live a wealth-free life, stowing away on freight trains and moving from town to town looking for campfires and a good can of beans. The Great Depression Theme Park isn't complete without these boxcar barons.
Having been everywhere, seen everything and met everyone, hobos are full of tall tales and song — not to mention sage advice. Some may claim to have been men of status (i.e., mayors or heavyweight champs) brought low by dumb luck, while others willfully renounced the stationary life. Both varieties of hobo will recount his story in detail, if you have the time.
These regents of the rails are never far from train tracks and almost always carry Bindle Sticks. Their natural habitats are moving boxcars and campfire circles, though ramshackle hobo metropolises do occur. Any gathering of five or more hobos will feature a hobo gentleman, identified by ragged top hat, cane and swagger.
Unlike street persons or the colloquial bum, hobos prefer rural settings, rarely panhandle, and generally conduct their affairs with some sense of dignity and etiquette. Newcomers to hoboism are often adopted by old timers and taught to observe some variety of "The Hobo's Code". When and how a hobo receives his nickname is unclear, but every hobo has one — it's usually "Boxcar" something.
Hobos are allergic to hard work, unless promised beans or alcohol, and are magnetically attracted to pies cooling on the window sill (whose aroma may cause spontaneous levitation). Kindly old women and farmers' daughters are friends of the hobo; police officers, bulldogs and employees of the railway ("railroad bulls") are natural hobo predators.
Bonus points are awarded whenever a hobo plays the harmonica.
Note: This applies only to hobos as a trope. Real Life hobos allegedly prefer to think of themselves as homeless travelers subsisting on odd jobs, whereas tramps travel without seeking work and bums do neither. We've yet to verify this with one of their rank, and note that calling a tramp or bum hobo elicits the same nonverbal response as calling him Gargamel. (Unless his name is Gargamel.)
- Kings In Disguise was serialized for years in Dark Horse Presents and later published in book form. It's a grim look at the desperate lives of hobos during the Great Depression, and deconstructs the carefree popular image of the hobo.
- In The Golden Age of Comic Books, Marvel Comics (then called Timely Comics, among other name changes) had a character variously called the Fighting Hobo or the Vagabond, who was a comical hobo who fought crime. These days it's panned as politically incorrect for glossing over the hardships of real hobos' lives.
- In The Goon Hobos appear as cannibalistic cavemen/jungle savages who have their own language. Their leader, the Hobo King may be a caricature of Woody Guthrie.
- The WALLE Forum Roleplay has several instances of this with the Undersite people, who escaped from a society that was no longer to their taste and withdrew in the sewer. Subverted by Dr. Grifton, who despite living in the sewer with them you'd not call a hobo at all.
- Bonus points for one of them, Hobey, who was actually a beggar before he joined the Undersite.
- The heroes in O Brother, Where Art Thou? are not hobos, but they briefly encounter some while attempting to sneak aboard a moving train. They still steal pies, though.
- They pay for the pies by replacing the pie with money held down with a rock.
- The film Emperor of the North, set in the 1930s, depicts the brutal battle between a sadistic train conductor and a legendary hobo nicknamed A#1. (A rare example of a realistic depiction of the hobo life in a Hollywood production.)
- In Meet John Doe, a reporter fabricates a letter from a John Doe who says he will kill himself on Christmas to protest the state of the country. When the story draws sympathy from the readership, she hires a former baseball player hobo to portray this fictional person in public.
- In the closing section of Pulp Fiction, Jules declares his intention to quit his job as a hitman, leave Los Angeles and "walk the earth" in the style of Caine from Kung Fu. His partner, Vincent, responds that he would be nothing more than a bum. Better a live bum than getting shot up on the toilet with your own gun, as Vincent finds out.
- The protagonist of Hobo with a Shotgun is a hobo who becomes a vigilante. With a shotgun.
- Pee-wee's Big Adventure - Pee-Wee encounters a friendly hobo when he hops a freight train, but the hobo's delight in singing old songs finally becomes too much for him.
- Who Is Bozo Texino? documents filmmaker Bill Daniel's 16-year quest for the most famous boxcar artist in history.
- Any of Charlie Chaplin's Little Tramp films.
- While hiking the Pacific Crest Trail in Wild, Strayed runs into a reporter from the Hobo Times who assumes that she is a hobo and starts interviewing her. She insists that she isn't a hobo, but has to admit that she doesn't actually have a job or a place to live.
- Woody Guthrie meets many during his travels in Bound for Glory, at one point riding in a railroad boxcar full of them. A hobo brawl ensues.
- Wild Boys of the Road: Lacking any better options, Eddie and Tommy start riding the rails, looking for work. It is a bad, bad life, nowhere near as romantic as it is often portrayed in other works. Hunger and fear plague the children as they travel across America. One child is sickened on the train by eating rotten food. Another is raped.
- Heroes for Sale: Tom and Roger become hobos and are treated horribly even though they are WWI veterans.
- The novel Sixth Column (also titled The Day After Tomorrow) by Robert A. Heinlein includes a hobo character. The hobo used to be a graduate student who decided to research the hobo lifestyle. He discovered he liked it and gave up being a student to be a hobo. He also points out to the protagonist that hobos are not tramps or bums, and in fact lays out an entire social taxonomy of American transients, with bindlestiffs at the bottom and true hobos at the top.
- Old blind Rhysling, the Singer of the Spaceways in Heinlein's The Green Hills of Earth is a kind of hobo. He's an unusual example, as he's built up something of a reputation as a wandering poet and is well-regarded by pretty much everyone.
- George and Lennie from Of Mice and Men, a novel by former hobo John Steinbeck.
- Spoofed by Tex Avery as hobo bears George and Junior.
- The climax of Fahrenheit 451 has literary hobos after Montag escapes the Mechanical Hound by jumping in a river. It is later revealed that these are all former English professors and stuff; they're keeping the books in their heads until contemporary society crumbles.
- In John Hodgman's The Areas of My Expertise, he gives a detailed history of the Hobo Conspiracy, including how a hobo (Hobo Joe Junkpan) once became Secretary of the Treasury and then gives 700 Hobo names (and 100 more in the paperback version). He does, however, make a point of distinguishing between normal homeless people and hobos (it's a lifestyle choice).
- In his Cities in Flight tetralogy, James Blish has the character Mayor Amalfi liken the titular cities to the migrants of the United States, saying that most cities are hobos, migrant workers, but some are tramps, basically petty criminals, and a few are the lowest sort: bindlestiffs, migrants who live by robbing other migrants.
- The main character of The Jungle becomes one by the end of the book, leading a happy life free of corrupting capitalism. Sinclair was known to bemoan the fact that people missed that this was the point of the book, not the meat factories.
- In the short story "The Haunted Trailer" by Robert Arthur, the narrator finds his trailer haunted by the ghosts of three hobos.
- Our Miss Brooks: Miss Brooks deals with hobos in the episodes "Hobo Jungle" and "Miss Brooks Writes About a Hobo".
- The Second Doctor from Doctor Who was basically a Space Hobo.
- It seems to be a running gag in iCarly where hobos are found or mentioned as a joke. In "iEnrage Gibby", Carly even has a "hobo party" where everyone dresses up a hobo!
- Hobos were present in pretty much all of his works, too. He actually offered a definition for the term and how it's different than just 'homeless' in a blog post. Not that it helped; multiple complaints forced iCarly to stop with the hobo jokes in 2011.
- Dave Attell encountered one on his show Insomniac with Dave Attell. After referring to him as a hobo, the man corrected him: "I'm a tramp."
- Don Draper had a life-changing encounter with a hobo, as he remembers in the episode: "The Hobo Code."
- In an interview on the "Funny Faces" video, Red Skelton described his "Freddie the Freeloader" character from his long-running TV series:
Red Skelton: “I get asked all the time; Where did you get the idea for Freddie the Freeloader, and who is Freddie really?
Well, I guess you might say that Freddie the Freeloader is a little bit of you, and a little bit of me, a little bit of all of us, you know. He’s found out what love means. He knows the value of time. He knows that time is a glutton. We say we don’t have time to do this or do that. There’s plenty of time. The trick is to apply it. The greatest disease in the world today is procrastination. And Freddie knows about all these things. And so do you.
He doesn’t ask anybody to provide for him, because it would be taken away from you. He doesn’t ask for equal rights if it’s going to give up some of yours.
And he knows one thing … that patriotism is more powerful than guns.
He’s nice to everybody because he was taught that man is made in God’s image. He’s never met God in person and the next fella just might be him.
I would say that Freddie is a little bit of all of us.”
- "Big Rock Candy Mountain" is a humorous folk song describing a fictional hobo paradise. Bowdlerized versions have been found on compilations of music for little kids; on the other end of the stick, probably in protest to the romanticizing of the hobo life, it has also been covered by the likes of Tom Waits, whose version is without accompaniment and consists of him slurring, screaming, and sobbing the lyrics even more drunkenly than usual. The original version, written by Harry McClintock in 1898, ends on this deeply cynical and very much non-kid-friendly note:
The punk rolled up his big blue eyes
And said to the jocker, "Sandy,
I've hiked and hiked and wandered, too,
But I ain't seen any candy.
I've hiked and hiked till my feet are sore
And I'll be damned if I hike any more
To be buggered sore like a hobo's whore
In the Big Rock Candy Mountains."
- "The Appleknocker's Lament", in a similar vein as the above, is about a boy taken in by the "big rock candy mountains" promises of a jocker, who proceeded to abuse and molest him during their six long months of traveling together.
- Roger Miller's "King of the Road" describes a "man of means, by no means", a hobo who travels about by boxcar wearing old worn-out clothes and smoking slightly used cigars, is well-known by the engineers and their families and well-acquainted with the handouts in every town, and two hours of pushing a broom earns enough to stay in an 8' x 12' room for 50 cents a day.
- Tom Waits himself has written "Bottom of the World" from Orphans: Brawlers, Bawlers & Bastards, a song about hobo life in Australia.
- Captain Beefheart's song "Orange Claw Hammer" is told from the perspective of a delirious old sailor who is "on the bum where the hobos run". Also note the song "Hobo Chang Ba", from the same album: Trout Mask Replica.
- "Hobo Jungle" by The Band is a song about the death of an old hobo.
- "Waltzing Mathilda" is the Australian version. It comes from a wave of German immigrants who brought with them some of their habits, such as nicknaming their awesome Great Coat Mathilda. A German swagman would refer to himself as "Auf der waltz mit mein Mathilda" (on the walk with my Mathilda), with all his belongings (swag) wrapped up in his coat.
- "The Ghost of Tom Joad", by Bruce Springsteen, is a hymn to the hobo life.
- Steve the Tramp was one of the early villains in Dick Tracy.
- Call of Cthulhu allows player characters to choose "hobo" as an occupation.
- Promethean: The Created basically has you playing [[Frankenstein's Monster Frankenstein
- Arkham Horror has "Ashcan" Pete, a hobo who makes a living being sneaky on the streets and traveling with his dog. He's one of the playable characters, and uses his sneaky stats to easily evade combat.
- The Others: One of the acolytes that the Sin player can choose is the Corrupted Hobo. They're not particularly strong (not that any of the acolytes are), but their ability allows them to be summoned once per turn to the board in a non-ranged fight and disable an upgrade that the player has for the remainder of combat.