Hobo Lit

America’s attitudes toward its most destitute citizens have always been sharply polarized. Consider, for instance, the philosophical divide between Emerson’s uncharitable self-reliance (“Are they my poor?”) and proto-liberal Thoreau’s opinion that “none can be an impartial or wise observer of human life but from the vantage ground of what we should call voluntary poverty.” Yet the ideas of self-reliance and voluntary poverty often converge in the classic American “bindlestiff” (or hobo) figure who hops trains or hitchhikes across the country, forever living on the margins of an unforgiving marketplace. And while the image of the homeless-by-choice hobo benefits from being associated with the dream of American independence and freedom, what about those rendered homeless by forces beyond their control? The non-voluntary poor hold no such privileged place in our collective imagination. The titles listed below go beyond historical myth, academic theory, popular prejudice, and newspaper statistics to address in more humane terms all the ways one can be homeless in America.

Beggars of Life by Jim Tully

Published in the mid-1920s, the sine qua non of American low-life narratives stands in stark contrast to the rumble-seat martini parties and rug-cutting flappers that dominate popular Jazz Age imagery. While Hemingway was in Gay Paree blowing his wife’s inheritance and Fitzgerald was conceiving aristocratic tragedies about wealthy gin-swilling depressives, teenage runaway Jim Tully was surrounding himself with “human wrecks, with degenerates and perverts, greasy and lousy, with dope fiends who would shoot needles of water into their arms to relieve the wild aching for an earthly heaven.” Tully’s grimy “novelistic memoir” of cross-country boxcar-hopping, bum fights, beggary, racial violence, petty thievery, and brick-through-a-window class warfare captures the ugly underside of life without romanticizing it. In doing this, he inadvertently introduced the “hard-boiled” writing style long before the term became associated with detective fiction. Beggars is as philosophical (“A tramp is merely a parasite who has not been admitted to society”) and poetic as it is faithfully mimetic: Tully’s uncommonly receptive ear allowed him to believably reproduce the speech patterns of America’s itinerant rural poor like no author since Twain. Popular in its day but snubbed by literary history, Beggars of Life is a cold, hard look into an American outsider culture all but ignored by official Roaring Twenties lore.

Travels with Lizbeth by Lars Eighner

Onetime psych-ward worker Lars Eighner’s late 1980s entrée into homelessness was hardly a pre-conceived immersion-journalism adventure. True, the title is an obvious nod to Steinbeck’s mutt-accompanied joyride memoir Travels with Charley. Yet Eighner isn’t on some leisurely quest to find the “real” America: his goal is to just survive on the streets until he can find a real job and a home. Priced out of their tumbledown shack in Austin, TX, the sporadically paid author and his dog Lizbeth initially hitchhike to California, where Eighner chases mirage-like job prospects. But soon he’s back in Austin, broke and homeless in a state where “a general contempt for the poor is reflected in a useless, vestigial social welfare system.” While camping illegally in a public park, Eighner perfects the art of Dumpster diving and learns to survive without resorting to panhandling or stealing. When not being harassed by fire ants, winos, meddlesome cops, or random thieves, the author and his steadfast pooch are engaged in the sort of “pointless circular rambling” that doesn’t exactly conjure On the Road romanticism. But thanks to the author’s defiant street-urchin reportage, we witness an outrage that goes far beyond the plight of a homeless guy and his dog: Eighner lifts the lid off the post-Reagan American Southwest to find the rotting remains of an outdated social system—one that still associated homelessness and poverty with criminality.

Night Freight by Clyde Rice

Rice was 84 when he penned this Depression-era autobiographical novella, which traces an unsuccessful gold-panning poet’s inaugural boxcar-hopping journey from Eureka, Oregon, to his family in California. The failed prospector sets out on his journey home empty-handed and half-starved. He soon forms some unexpected bonds with a cast of roadside prophets that include “professional” bums, a disgruntled ex-sheriff, a drifting shoemaker, and a Marxist revolutionary, all living out their raggedy utopian ideals in the shadow of the American Dream. Dickens’s ghost looms over much of this, especially when it comes to Rice’s tendency to portray normally inanimate objects as being vital and alive while humans are sometimes described in machine-like terms. The workhorse locomotive at the center of the novella is just as memorable a character as any of its passengers: its clanking, shrieking, tie-connected body winding through the Siskyou mountains like some serpentine pack animal lamenting its Sisyphean fate. In this way, Rice’s observances of vagabond life in Night Freight make extraordinary sensory events of the most mundane aspects of human experience.

Hobo by Eddie Joe Cotton

Gen X’s most famous self-styled, suit-wearing hobo, Cotton left his father’s brickwork business in 1991 and embarked on a coming-of-age train-hopping tour across the country, ostensibly bound for Mexico. This memoir covers the months he spent tramping his way from Denver to Las Vegas, but it’s probably more a travelogue about Cotton’s love for middle American kitsch and truck-stop culture than his willingness to bond with the less fortunate. Cotton’s at his best, though, when objectively observing the hard reality of the hobo life rather than playing up its rosy Americana mystique. What makes Hobo unique is Cotton’s ability to so clearly define and interpret the lifestyle and to shape his accumulated knowledge into a trusty how-to guide for aspiring slackers. The book comes equipped with a full glossary of hobo-related terminology while dispensing such potentially useful rail-riding wisdom as how to keep warm without a blanket, how to dodge railroad police, how to conduct yourself in a hobo “jungle,” and how to tell the difference between a bum, a tramp, and a hobo. What’s more, Hobo can be a handy traveler’s resource—especially if you’re looking for an insider’s guide to Winnemucca, Nevada.

Sister of the Road: The Autobiography of Boxcar Bertha as told to Ben Reitman

At a time in the 1930s when close to 25,000 homeless women were hopping trains looking for work, “Boxcar” Bertha’s 15-year stint on the road engaging in petty crime, prostitution, drugs, and radical politics seemed driven by her predilection for the hard life as much as anything else. From a long pedigree of Midwestern working-class leftist radicals, free thinkers, and free lovers, Bertha is raised among freight yards, brothels, and boarding houses, and educated in a socialist co-operative colony. At 16, the brawny blonde set out for existential fulfillment hitchhiking and hopping freight trains from the Midwest to the East Coast. Eventually Bertha’s gluttonous quest for love and adventure comes at a price: one of her lovers, the ringleader of a band of shoplifters, is eventually convicted of murder and hanged. Another beau loses his legs under a train’s wheels while she watches helplessly. But Sister of the Road is more than straight autobiography. It’s also a cross-country panorama of a long-lost bohemian expanse of Depression-era America: the book’s noted brothels, bughouses, jails, hobo colleges, IWW halls, drug dens, bootleg joints, and protest marches help mark a time in US history when it seemed the once-chugging engine of capitalism had finally lost its steam.

Tell Them Who I Am by Eliot Liebow

Tell Them Who I Am was written and researched in the early 1980s, around the time Ronald Reagan’s elitist trickle-down economic policies were helping to create the modern face of American-style homelessness. After being diagnosed with cancer, sociologist Liebow decides to live among residents of a women’s homeless shelter in Washington, DC, and document the everyday reality of their lives. Liebow’s participant-observer perspective dismantles the then-prevalent caricatures of homeless people as lazy and unwilling to work. Liebow’s writing is basic bricks-and-mortar craftsmanship but also porous enough to absorb the frustration and anger radiating from the surprisingly hopeful women interviewed here. Controversial for its time, Liebow’s conclusion was that these women, representing a broad cross-section of racial backgrounds, weren’t failures despite a successful free-market system; rather, they were victims of a broken free-market system’s failure to provide for those unable to conform to its strict behavioral codes. This is, on the one hand, an intensely personal study of homeless women bravely coping with loneliness, boredom, job instability, and society’s innate fear of homeless people. But there’s also an informed institutional critique at work: Liebow finds that the American social service system’s aim of “helping people to help themselves” often leads to cruelty and abuse rather than charity and compassion.

The Last Known Residence of Mickey Acuna by Dagoberto Gilb

Having a roof over your head doesn’t mean you aren’t homeless, as evidenced by the life of daydreaming, drifting protagonist Mickey Acuna in former journeyman carpenter Gilb’s debut novel, set amid the dusty tumbleweed streets of West Texas. With his entire life stuffed in a duffel bag, Mickey shuffles from one unskilled job to another, eventually trading his flophouse tenancy for what he thinks might be the prelude to grander things in life: temporary residence and part-time work at the El Paso YMCA. Gilb’s subversively simple naturalistic style bears the unmistakable stamp of life experience and shows a rare sensitivity to the Southwestern region’s much-ignored underclass. Through Mickey, we get the sights, sounds, and vicious-cycle psychology of poverty: Gilb deals directly with the sort of self-perpetuating illusions that lead one not backward or forward in life, but forever sideways—a lateral slide into a vaguely envisioned future. And as Mickey comes to realize, once you lose yourself in the wanderer’s life, it’s damn hard to find your way out.

Without A Net by Michelle Kennedy

Kennedy’s recent memoir is testament to how easily an intelligent, mentally fit young woman can go from college student to middle-class suburban wife to living hand-to-mouth in a rusty Subaru with her three small children. When Kennedy’s husband quits his job in DC to live Unabomber-style in a rural cabin, Kennedy dutifully follows him, bearing his children with the speedy efficiency of a sharecropper’s wife. But once the couple’s unromantic bucolic reality sets in, Kennedy collects the kids and leaves her broke, selfish hubby for the sunny prospects of independence. Next thing you know she’s bussing tables at a Maine pub. And sleeping in her car with the kids. Although plenty of obvious lapses in judgment led to her predicament, it’s difficult not to admire Kennedy’s determination in the face of squalor and penury. She diligently stashes her tips and below-minimum-wage salary in the glove compartment for an entire homeless summer until she can afford a place to live. Along the way, she gets hit with the hard reality that obtaining food stamps can be more difficult than finding affordable housing. And she questions perhaps the most head-scratching free-market economy paradox of all: why is it often more expensive to be poor than rich?

A former staffer at Pitchfork and Popmatters, Michael Sandlin has written for the Village Voice, Time Out New York, and various other print and online publications.