Every now and then I come across someone on the subway who defies easy categorization. I remember, for instance, a man who boarded the 3 train in Brooklyn a few years ago wearing military fatigues and a bandolier packed with little glass bottles of liquids. “Who is man enough to buy my fragrances?” he shouted. (When one rider replied that he wasn’t sure, the man responded, “Are you man enough to kill a hooker in Moscow with a crowbar?”) More recently, there was a man on the uptown 6 wearing a pair of oversized New Year’s glasses—the ones where the 0’s serve as eyeholes—who played atonal jazz on his saxophone and asked for no monetary compensation in return. I could keep going, but no doubt anyone who has lived in a city for any length of time has their own mental list of these self-styled subterranean eccentrics, grouped together not so much by any particular characteristic other than the fact that they seem only to exist underground.

Over the years I’ve made casual study of this joyful band of accidental philosophers as they’ve decorated my dreary morning commutes with their Bedazzler guns of mischief. A few months ago I had the good fortune of getting to know one of them on the R train. I was reading Joseph Mitchell’s Up in the Old Hotel when a man whom I’ll call Z. (because he asked me not to use his name) approached me and said, “That’s a great fucking book.” In short order, Z. unwound his own, self-proclaimed Mitchell-esque story for me: Now in his sixties, Z. told me he spent his life wandering the world, setting up shop as a tour guide in various cities in Europe and Asia; a sort of tourist of the tourism industry. He claimed to have known the last great Tammany boss, Carmine DeSapio—“you got one favor a year”—and to have once lived in Frank Serpico’s apartment. He spoke of corruption in the Church of England and a long-gone love from Peru. These days, he’s “between a few places,” he said, passing his time chatting up strangers on the subway and in Christopher Park, a block-sized patch of grass in Greenwich Village. (“It’s the last vestige of decrepitude,” he explained.) When I asked Z. why he chose this life of wandering and park benches, he told me he that if I wanted to understand people like him I should go read a book called Subways Are for Sleeping.

Published in 1958 by the journalist Edmund Love, Subways Are for Sleeping chronicles the day-to-day lives of a handful of transient New Yorkers that Love met during a year he spent living on the street. “I was caught up in a whirlwind,” Love wrote in the introduction. “When it all ended, I found myself walking the streets. I needed more than just a job. I needed to reassess life … So I drifted.” The books is essentially Love’s personal list of subterranean eccentrics, the mid-twentieth century’s brand of atonal jazz masters, perfume salesmen, and tourism tourists. He dubbed them Twilight People, which he defined as a transient class of city wanderer distinct from the downtrodden lonely types that have come to be associated with the notion of homelessness. Twilight People, as Love described them, were hopeful and intelligent, living “by and large, by their wits … most of them have no regular job; only a few of them have a normal home.”

Take Henry Shelby, the subject of the book’s title essay. Shelby lived on the subway, though he spent his days above ground, traveling exclusively by foot (“subways are for sleeping,” he told Love). Occasionally he’d work an odd job, earning enough for a shave in the bathrooms of a train station. But he spent most of his days exploring Manhattan, studying everything from shipping routes to police behavior, making it his business to collect arcane knowledge of the city. He discovered, for example, that after 7:30 P.M., only gentlemen wearing horn-rimmed glasses could sit in Grand Central and read a book without being harassed by the police; curiously, however, anyone could read a newspaper unbothered as late as they pleased.

Love’s Twilight People all share this trickster’s dual existence: willfully out of step with everyday people but brilliant at exploiting them. There’s the story of Sam Victor, a 250-pound homeless man who worked with Love at a warehouse some sixteen hours a day as he pursued his lifelong goal of winning big on a single bet at the racetrack. To this end Victor would stay up three or four nights in a row, fueled by more than a quart of whisky a day. (“By any other standards than Sam’s, he would be called an alcoholic,” Love wrote. “Yet I never saw him drunk in all the time I knew him—unless he was always drunk.”) Like all the Twilight People in the book, Sam led a transient life. He grew up in Ohio and played for twelve years on the Cleveland Indians and the Philadelphia Phillies. Then he married a woman in California who left him after he ran up a $687 bar tab in the first month of their marriage (in today’s dollars, that’s $6,394.68). In roughly this fashion, Sam Victor—never drunk or casual with people’s hearts—drank and gambled his way through five more marriages. It wasn’t that his wives didn’t love him. Indeed, he kept a full wardrobe at each of their homes, where he frequently crashed, sleeping for thirty or forty hours at a time. “The most important word in the English language to him was friendship,” Love wrote. “In its name anything was forgivable. He expected friendship to go both ways.” His wives all cared for him, forever offering him the comfort of their affections, but they simply could not bumble through life in the manner he preferred.

“These are people like the man who takes a shortcut to explore the countryside, forgetting completely why he took the shortcut in the first place,” Love wrote. “To them there is more security in a home on a fire escape or a job washing windows than there is in a furnished apartment or a regular job. An apartment might burn down. A man with a regular job might get laid off.” This idea that Twilight People chose homelessness was, for Love, essential. It was not out of desperation but honest desire. They lived whatever life they wanted for exactly as long as they wanted or needed. Consider the story of George Spoker. Spoker was once a banker in San Francisco until it was discovered he had been skimming the books. He did two and a half years in San Quentin. Upon his parole, he moved to New York equipped with a $78 a month family inheritance (about $700 today). Despite his wealth, Spoker chose a transient city life. He bounced around flophouses and then began seeking out free places to eat, sleep, and wash, keeping track of the locations in a notebook. He did this for years, eventually settling on a park bench where he became a sort of consultant for the down and out—once even securing a job for Love. Soon, Spoker was cleaning and feeding the city’s homeless, employing them as caterers for the downtown Manhattan office crowd. In time his catering business became wildly successful; Love estimated Spoker made around $10–12,000 a year (about $92,000 today). Nevertheless, Spoker kept his post on his park bench. He lived as a homeless man doling out advice to the less fortunate until, years later, he fell in love. He moved up to Westchester for his relationship and soon found himself commuting back and forth to his park bench. Finally, he gave up the homeless life. “There is nothing the matter with being a bum,” he told his friends. “But when you have to commute thirty miles every day there’s just no percentage.”

A few weeks later I met up with Z. in Christopher Park. I told him I had read the book and—in the vain hope of trying to understand why he chose never to “put down roots,” as he put it—I asked him which characters he most related to. The stories were “just stories,” he replied, explaining that he was not particularly impressed with the individual lives of any of Love’s Twilight People. (In retrospect, this response was to be expected; I suspect even an astronaut finds the daily routine of other astronauts mundane.) Z. said that more than anything, it was Love’s introduction that kept him returning to the book. Particularly, it was Love’s description of Twilight People as “waiting.” “Waiting” was the word Z. kept using. It appears in only one passage in the introduction:

[T]hese people I write about are not really bums. The big difference between them and the real, down-and-out bum could be called a matter of hope. I recognize in them something of what I felt in myself. Most of them are in a state of reassessment. They have come up against something which they cannot understand, and which they want to think about. The thinking is important to them. My people still believe in miracles. Your average bum does not. He has given up hope. Most of my people are living stop gap lives. They are waiting for the big break. That break may be a call from the producer of a Broadway show. It may be a horse that gallops home at 40-1. It may be just a bright and shining light that suddenly comes to show them the way out of the jungle. Some aren’t sure what kind of a break they are waiting for, but they have assured me that they will recognize it when it comes. In the meantime, they wait and try to keep going through today, for tomorrow may bring any miracle. Tomorrow is always a big day.

What exactly Z. had come up against, and what he was waiting for every night as he sat in the park, I’m not sure. He never seemed to understand it either: “Music is notes and blanks. You need both,” he told me. “I’ve got a lot of blanks in my life.” These day’s Z. gives tours of the Village to out-of-towners who are hoping to see locations used on Sex and the City or to eat at some fusion restaurant they saw on the Food Network. He entertains these people only because he’s trying to earn enough money to go to India. “I keep coming back because my roots are here. I never made new roots so I have to come back. Even though I hate this fucking place,” he told me. “Now everyone’s a tourist.” I pointed out as politely as possible that he had essentially spent his life traveling around the world and that everywhere else he went, he too was a tourist. He conceded this fact with a skepticism that suggested I’d somehow failed to understand the point of Love’s book, which I imagine was something like this: There are those of us—most of us—for whom subways and city parks are just stopovers, waypoints on the way to where we are going. But the Twilight types feel at home with the movement. Constantly traveling themselves, they are perhaps unaware of any motion at all. In Subways, Shelby explained his lifestyle choice to Love this this way: “I don’t have much trouble. I’ve never gotten drunk and lain in a doorway all day,” he said. “Things seem so easy and natural this way, the way they are now, that it’s just as though it was supposed to be this way.”

The last time I met with Z. was in late spring on his bench in Christopher Park. We had spoken for a few hours and our conversations had begun to repeat themselves. I got the sense Z. was ready to find a fresh ear for his stories. I shook his hand and wished him well. As I got up to leave he called to me: “Look,” he said, laughing as he pointed to a group of tourists. “These are my people.”

Joe Kloc is a writer and illustrator living in New York.

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