In this series
In this series










This series on homelessness is what journalists call an explainer. If you’ve been reading along week by week, by now you know much about the facts of homelessness, including both its personal and societal causes.
Now we’re getting to proposed solutions—and I’ll lay groundwork with a brief survey of the long disposition in American culture that pushes many of us to look for answers to homelessness in all the wrong places.
First, consider the 1933 hit movie Hallelujah, I’m a Bum. Al Jolson plays Bumper, a homeless man who lives most of the year in the Hooverville of New York City’s Central Park, then winters in Miami. Bumper, in his 40s, has chosen homelessness because of the freedom it affords. He sings, “You’ve got the grass, / You’ve got the trees. / What do you want with money?” Others among the homeless respect Bumper and call him Central Park’s “mayor.”
Then, after falling in love with a woman suffering amnesia, he puts on a coat and tie so he can work in a bank and settle down with her. “I’m not a tramp anymore,” he declares. “I’m going to get promoted, then I’m going to get promoted again. I’m going to have an office.” But the woman regains her memory: She is the girlfriend of the real mayor of New York, and she goes back to him. Bumper quits his job and comes back to his senses—and the good homeless life: “You’ve got the air, / You’ve got the breeze, / What do you want with money?”
Three decades later, in 1965, Roger Miller’s “King of the Road” hit No. 1 on the Billboard Country chart. For weeks it ruled radio: “Trailers for sale or rent. / Rooms to let, fifty cents.” The song won five Grammys and had legs: Dean Martin, George Jones, and Randy Travis later covered it.
Miller’s tune was snappy and its message happy. The king of the road has freedom and independence: “Don’t pay no union dues.” He doesn’t have to work all day: “Two hours of pushin’ broom / Buys an eight-by-twelve four-bit room.” He’s not isolated: “I know every engineer on every train. / All their children, all their names.” He’s rich in not having to follow dull rules: “I’m a man of means by no means, / king of the road.”
Come 1997, scholar Gwendolyn Dordick published her PhD sociology dissertation, Something Left to Lose, describing her time with four groups of homeless New Yorkers. Some lived in the huge west side bus station, some in a shanty town on the east side, some in a large public shelter at the northern tip of Manhattan, and some in a church shelter.
Each place came with tradeoffs. Station and shanty offered freedom—but no material security. The public shelter yielded food and a bed, “three hots and a cot,” but also danger. Dordick contrasted the unpredictability, squalor, and risk of life in the church shelter. There, the inhabitants were “safe and well fed,” but they were required to work, get their GEDs, and attend Alcoholics Anonymous meetings.
Dordick depicted those rules as patronizing and invasive. At the church shelter, “the men live in a fishbowl,” she complained, “their progress monitored constantly in the logbook by well-meaning volunteers who want their clients to be more like them.” Ugh: sober, self-controlled, bourgeois. She “came to understand [the church shelter] best in terms of what it lacked,” Dordick wrote. People there “lived in conditions that were materially better and more secure,” she acknowledged, but said “they had clearly given up something in return.”
Here in 2026, another 30 years on, a review copy of a 2024 book is in my mailbox: Neil Gong’s provocatively titled Sons, Daughters, & Sidewalk Psychotics: Mental Illness and Homelessness in Los Angeles. The role of individual autonomy—or lack thereof—is a central theme of the work.
America’s anti-institutional instinct predates the establishment of the United States. George Washington was the father of our country, but Jean-Jacques Rousseau, who died in 1778, its uncle. He advanced the notion that people are naturally peaceful and good, “noble savages”—until social and economic structures, along with self-interest, mess us up.
That archetype remains with us to this day and is often tied to homelessness. Even comic books have noble savages who live outside society’s strictures.
In the 1960s, Captain America lived in cheap hotels then hit the road on his motorcycle. In 1987 and 1988, “Homeless Avenger” comic books celebrated a “punisher dedicated to protecting the homeless and homeless people of New York.” Relative Heroes comics in 2000 featured homeless orphans running from the government after their parents’ deaths. And in 2021, Marvel Comics introduced a gay Captain America and made him homeless too.
The Rousseau-style emphasis on personal autonomy is so widespread in our culture that it finds a place in Disney films like Frozen, where the main character sings, “No right, no wrong, no rules for me. / I’m free.” Who in the real world follows their own inclinations and lives free of the rules? In some romanticizing eyes, the homeless: “independent urban noble savages.”
The website TV Tropes, which documents common trends and story templates in modern media, has documented many more examples than I can give here, including the “Magical Homeless Person,” “Wisdom from the Gutter,” and the “Magical Barefooter.” So the meme lives on, encouraging an anti-institutional and pro-autonomy ethos that makes homelessness more difficult to understand and address.
