No illustrations for this one, friends: just songs and stories.
According to Wikipedia, the technical definition of a hobo is a wandering homeless person, usually a man, especially the ones who hop trains, riding on empty freight cars from place to place. A hobo would differentiate himself from a tramp--who would travel but not work--or a bum--who did neither. A hobo prided himself on doing both, but society at large seldom made such distinctions.
Although hobo culture (the derivation of the term hobo is hopelessly intricate, and I won't even attempt to untangle it) began to develop in the years after the Civil War, as a phenomenon its glory years were during the Great Depression, which began in 1929. Coincidentally, those years spanned the career of Jimmie Rodgers, a former railroad man himself, who met hoboes in the course of his work and turned their stories into songs of gentle ironic humor, pathos and poetry. His most famous songs of the hobo lifestyle are "Hobo Bill's Last Ride," "Hobo's Meditation," and "Waitin' For a Train." "Hobo Bill's Last Ride" is an especially sentimental but nonetheless affecting piece about a hobo who is dying, alone, on a boxcar, on a rainy winter's night. It concludes with a chilly comment on society's dismissive attitude toward these men who rode the rails:
There was no mother's longing to soothe his weary soul
He was just a railroad bum who died out in the cold.
That one has been covered by several singers, but none of them quite match up to the original; Hank Snow probably came closest.
I have already mentioned the Parton-Harris-Ronstadt cover of "Hobo's Meditation," with lead vocals by Linda Ronstadt; it's quirky and the harmonies are flawless. As for "Waitin' For a Train" my favorite cover was by Jim Reeves. Put off the train in Texas--"a state I dearly love"--by a brakeman, the hobo ends his song
My pocketbook is empty, my heart is full of pain
I'm a thousand miles away from home, waitin' for a train.
Hank Williams Sr. did a series of recitations in the course of his short career under a name that would be appropriate for a hobo--Luke the Drifter--and a few of his songs make reference to the hobo life, most particularly "I Heard That Lonesome Whistle Blow." However, since the nameless protagonist of that song ends up in prison for life, it is usually classified as a prison song.
Next up is the immortal cheeky 1965 Roger Miller classic, "King of the Road." It is sui generis; there is no other hobo song quite like it, and though George Jones among others tried valiantly to cover it, nobody ever sang it with Roger Miller's joyful insouciance. This is one that nothing will do but the original, if you want to check it out.
May I also mention the great Boxcar Willie (1931-1999), who performed parttime as a singer in the hobo style (complete with the layered clothing and scruffy unshaven look) throughout a twenty-seven year career in the Air Force, only becoming a full-time entertainer when he left the service in 1985. Born Lecil Travis Martin, he met hoboes in train stations in the 1940s and wrote a number of his own songs, in addition to performing Jimmie Rodgers with an elan that would please the Singing Brakeman himself. I used to listen to the Grand Ol' Opry a lot; Box was a member beginning in 1981, and one of my fondest memories of him was a night he did an entire set of Hank Williams songs. He alone of all those who have made the kamikaze flight of singing Hank Williams did not embarass himself. My favorite of all his recorded performances, though, is a duet from Hank Williams Jr.'s 1981 album THE PRESSURE IS ON. Called "Ramblin' in My Shoes" it's an exuberant celebration of trains, hoboing and great music.
No doubt I've missed a whole lot of great performers and performances; Woody Guthrie, for example, was a hobo for awhile, and his experiences turn up in his music. Bob Dylan was never a hobo, but he sang about them. Hopefully, though, I've hit the high points.
Thanks for holding your yawns, and till next time, fair thee well.

PS It's official. Miss A DOES NOT have mono. One less worry.