On the Rail

September 27th, 2010  |  Published in Uncategorized

On the Rail: True Stories from a Great American Train Ride
Yale Daily News Magazine, 2.12.07
Generations past its golden age, is there any romance left on the railroad?

Green is probably the last word that comes to mind when one thinks of Los Angeles. Smog, earthquake, ocean, anorexia — these are all more realistic free-association choices. But for the 62 hours I spent chugging across the country on an Amtrak train last month, Los Angeles loomed on the other side of a dark continent like the green dock light Jay Gatsby so longingly watched in F. Scott Fitzgerald’s The Great Gatsby.

I invoke Fitzgerald because it is the current state of the great American train ride that I hoped to investigate on my own cross-country journey. Gatsby’s narrator, Nick Carraway — a Yale Daily News writer himself — describes the way his return trips from Yale made him “unutterably aware of [his] identity with this country for one strange hour, before [he] melted indistinguishably into it again.” I decided to see what had become of this vision — to search for some trace of the romantic railroad days of yore on a modern cross-country train trip.

The itinerary called for a 19-hour jaunt from New York to Chicago on the Lake Shore Limited, followed by a five-hour layover in the Windy City and a 43-hour ride from Chicago to Los Angeles on the Southwest Chief. My cohorts were not the Midwestern gentry with whom Nick Carraway traveled; rather, they were three good friends from my suburban New York public high school. And unlike myself, Julien, Adrien and Kateri were not on a quixotic mission to satisfy some obscure literary hunger. They just wanted to have an adventure.


January 4 dawned clear and unsettlingly warm in New York. I hadn’t even packed a winter jacket. As we descended a Penn Station escalator and emerged amongst a mob of travelers who moved with all the energy of a late August afternoon, I began to grow nervous that I would never catch a glimpse of Carraway’s wintry wilderness.

At the edge of the platform, a squat, bald conductor was barking at the arriving passengers in broken English.

“Chicago in last car!” he shouted. Upon arriving in our car, we found two pairs of seats next to each other on the platform side of the train. The car seemed a relic of the late 1970s — seats were upholstered in garish shades of red and orange; magenta curtains swung from the windows. The entire interior looked like some sort of gaudy disco library. As I settled into my coach class seat, which offered the ample legroom of a first-class airplane seat, the conductor ambled into the aisle.

“This the four o’clock train to Chicago!” he exclaimed. “Next smoke-break in two hours.”

The dim lights of the Penn Station platform gave way to the dimmer and more intermittent lights of the underground tracks, and within minutes we were zipping along the Hudson River. The sun hung low above the water, dripping like a great luminous egg yolk toward the Palisades. We glided under the George Washington Bridge, cleared Manhattan, and by 4:30 we had passed Hastings-on-Hudson, the riverside hamlet from which Julien, Adrien, Kateri and I had departed two hours earlier. Forty minutes later, as we passed the Indian Point nuclear power plant at Peekskill, the sun collapsed into a soft orange puddle at the edge of the Hudson.

It was around this time that I began to survey my fellow travelers. Kateri and Adrien sat in front of Julien and me. Across the aisle, two youngish Chinese women were conversing in Mandarin (the conductor had stopped by to flirt with them earlier); in front of them, a young German couple canoodled while watching a game show on a portable DVD player. I glanced back at the rest of the car. Behind us, a middle-aged black man was reading a book; across from him, a pair of grizzled white men spoke in low voices, chuckling occasionally. Beyond them, the rest of the passengers seemed to all be people younger than 30 or older than 50, diverse as the occupants of a New York City subway car.

A stocky, bestubbled college-aged man was now speaking to Julien; they had taken an engineering course together at Columbia. He introduced himself as Elliot, a grad student heading back to Madison, Wisc., after vacation. I asked him why he was taking the train.

“It was cheaper than the plane, on short notice,” he said. “I think you have to be old, poor, or young to take the train. And you have to be a lot friendlier when you’re spending seventeen hours with the same people.”

I told him that I was going all the way to Los Angeles.

“After Chicago, things get stranger,” he mused. “Then you get all the hippies.”

We chatted for a half hour about the future of commercial cross-country train travel before the conductor emerged again.

“Albany coming up soon,” he exclaimed. “You have fifteen minute smoke break. Better smoke two cigarettes at same time, baby!”

The five hulking homogenous office towers of Albany’s skyline soon crept into view, a Le Corbusier daydream shrouded in an eerie blue-green glow. The train came to a stop and we jostled our way to the door. Already, a crowd of smokers had lined the platform, their fumes mingling with the suddenly-cold night air. I ducked into the station to buy some coffee. On the way back, I noticed a middle-aged woman wearing a Harvard scarf. Just as I was about to ask some convoluted question about Nick Carraway’s vision of American identity as constituted by the cross-country train ride, a voice on the loudspeaker announced that my train was about to depart. I hurried back to my seat.


Albany gave way to warehouses and dim streets lined with dingy houses. Occasionally we would pass a generic strip of neon-emblazoned stores and restaurants. No wilderness yet. Somewhere around Utica, the restroom door clanged open, unleashing an eggy fart smell into the entire car. The women across the aisle groaned. The Germans started making out. My comrades and I decided that it was a good time to head up to the diner car.

The hot food counter was closed, but there were still about ten people scattered around the cafeteria-style tables. A boy of about thirteen sat scribbling in a math book. A college-aged brunette sat gazing out the window. We sat down across from two men who had just finished a game of blackjack. They smiled and introduced themselves. Reggie and Damian (names changed for this article) were both from the same block in Harlem, though they had never met before tonight, and they were both on their way to Chicago. A bottle of liquid — which was eventually determined to be a concoction of Hennessey and Gatorade — rested on the table in front of them. Reggie had a round face framed by a navy New York Yankees hat and a closely trimmed beard. Damian had a thin face and cornrows that dangled out the back of his baby blue Texas Rangers hat. I asked why they were taking the train.

“Man, I ain’ want to be stuck next to no fat lady,” Damian said, revealing a thick Jamaican accent. “I took de Greyhound bus up fram Flarida one time an’ I ain’ never been so uncomfortable in my life. An’ I really don’t like the plane either.”

“I couldn’t fly because of all those background checks,” Reggie said. “I mean, I ain’t no terrorist or nothin’, but I didn’t want to deal with all that, you know what I’m saying? Hey Damian, why you going to Chicago?”

“Visitin’ my uncle,” Damian said.

“I’m going to pick up my baby boy,” Reggie said, his smile revealing two missing front teeth, which he later told us were knocked out by a drunkard who thought Reggie was a crack-head.

“Baby mom left before my son was born,” Reggie continued. “Her dad said he’d pay her rent if she came home. I wanted to struggle through, you know, try to make it work, but she left. So now I’m going to pick up my boy and take care of him for a few months.”

“Does dat mean no more Henny and Gatorade?” Damian asked. “You gonna be a responsible adult?”

“I’ll get all that stuff out my system on the way up,” Reggie replied. “I’m just worried the cops will see me with a white baby and try to take him away. His mom’s white. Black, white, it don’t matter to me. That’s how my crew rolls, you know? Not everybody’s that way. You know, some kids came up to me earlier and asked me for drugs. Just cause I’m black don’t mean I hustle. But hey. Let’s play cards.”

We played War until Julien and Reggie reached a stalemate. At Syracuse, Julien went back to the seats to sleep. The brunette started playing cards with Reggie. I played the documentary about Yale’s “We Suck” prank on my laptop (Damian’s reaction: “Da’s awesome.”) We spent a half hour watching Damian’s DVD of a 24-hour Jamaican reggae concert. Performers switched between English and Patois; dreadlocked fans spewed smoke from overloaded joints.

“You know, in Jamaica, it ain’ even no ‘ting,” Damian mused. “You can buy a pound for 50 dollars American. I like to cook it up in my collard greens.”

We laughed. Damian was about to say something else when the boy who had been scribbling in the math book piped up from the next table.

“Last time I smoked was three weeks ago!” he said brightly. “Makes me want to just go do some of that shit in the bathroom right now.”

Damian gave a look of horror.

“Wat he talkin’ ‘bout?”

At this point, a man who looked like Groundskeeper Willie from “The Simpsons” emerged from his seat, asked if he could buy whiskey from us, and trundled off dejectedly when we said no.

“Bedtime?” Adrien said, turning to Kateri, then me.

“Bedtime,” I agreed.

As I lowered myself into my seat next to an already-snoring Julien, felt the car rattling feverishly along the tracks, and smelled a fresh waft of the eggy fart smell from somewhere in the not-so-distant distance, another layer of the romantic train myth slipped to the quivering floor like a dry snakeskin. Sleeper cars may have been cheaper in the old days, but the Nick Carraways of the world can still pony up an extra $100-$200 a night for a bed at the head of the train today. The rest of us — poor, old, or young — were doomed to wake up to whatever was left of the Great Midwestern Wilderness groggy and achy-backed.

Somewhere around Rochester, I drifted into an uneasy and intermittent sleep. Old Rust Belt cities flew by in a haze of pinky-orange light; lonely traffic signals blinked vainly at shallow puddles in damp deserted intersections. Around four in the morning, I awoke to the sound of the man behind me speaking on cell phone in a low, sonorous bass.

“I do love you, baby,” he cooed. “With all my heart and three inches of my soul. I’ll be the first to admit, I was a bad little boy.”

It was like Isaac Hayes was doing a voice-over inside my ear.

“How much salad dressing? A quart?”

I drowsily attempted to wrap a sweater around my head.


By South Bend, Ind., the dim haze had brightened somewhat. Flat fields rolled by us in the early-morning mist. A young man sitting two rows ahead of us offered Adrien a bagel; the Germans had awoken and were brushing each other’s hair. The conductor came in and turned on all the overhead lights.

“Rise and shine!” he said. “Come up to dining car. Best breakfast you ever have.”

I looked at my watch. It was six in the morning. I closed my eyes and buried my face in my jacket.

Sometime later, Julien shook me awake — Chicago. We disembarked, dumped our bags in a locker at the station and wandered out into the city. On the street, we saw Reggie standing next to a young woman, holding a baby. He saw us and grinned.

“Y’all take care now,” he said. “And if you’re ever in Harlem, swing by my block.”

We slapped hands and headed out into the gray day toward the lakeshore. Even though it wasn’t terribly cold for a January afternoon in Chicago, I was already pining for some California sunshine, not to mention the real bed that awaited me there.


Nick Carraway was right about Chicago. Getting there is a chore, but leaving the Windy City for the wide reaches of the unknown West is distinctly exhilarating. When the Southwest Chief lurched into motion, Carraway’s “sharp wild brace” began to stir in my blood. Within an hour, we had cleared the western suburbs and soon we were racing across the great plains of Iowa into the shadowy dusk. Inspired, I picked up my copy of Gatsby, which I had meant to start reading on the previous train. As I sat in the warm glow of the reading lamp, leafing through the browning pages, I felt that some English professor somewhere would have been very proud of me.

When we stopped in Kansas City, Adrien and Julien started talking to a girl who had just boarded the train, and Kateri snoozed in her seat, but I remained blissfully engrossed in my book. We were just starting to move again when a bloodcurdling wail rousted me from my metaphysical basking.


A screaming toddler had just boarded the train, followed by a more silent toddler, two flustered parents and the conductor. As I silently prayed for their expeditious passage to the next car, I noticed two more families with young children in tow. Much to my chagrin, the first family sat down right behind me, and the other two began to situate themselves in the following rows.

“WHAT IS LOS ANGELES?” the little girl behind me shrieked.

My green light? The hallowed land of sunshine and swimming pools and real beds?


“Well, honey,” the girl’s father said, “it’s a … it’s the … it’s where we … it’s the name of the really big place where we live.”


I turned to my handy Amtrak pamphlet, which informed me that Los Angeles was “the sprawling metropolis that began in 1781 as El Pueblo de Nuestro Senora de Los Angeles.” I briefly considered offering this explanation.

“It’s where we’re going,” the girl’s mother said, finally betraying a hint of irritation. A momentary silence suggested the girl might be satisfied.


Adrien and I quickly grabbed the 32 oz. bottles of Fat Tire Ale we had purchased in Chicago and left for the relative peace of the snack car. When we returned to our seats an hour later, everyone was asleep, including the children. Gleefully, I reclined two nearby vacant seats as far as they would go, snuggled up with my sweatshirt, and closed my eyes, falling asleep to the gentle patter and squeak of the tracks beneath me.


I awoke at base camp. Blinding rays of white light gushed in through the open windows, and I looked out to find Colorado caked with a thick coat of fresh snow. It seemed as if the previous night’s snowfall had infiltrated the train itself — people all around the car were groggily grabbing bulky jackets. I overheard someone say that eight inches had fallen in Denver the night before. I dug out another sweater.

“I liked the hotel we stayed at better,” the little girl said. “I wish we could have stayed there longer.”


The Southwest Chief bears little resemblance to famous Expresses like Orient, Polar, and Hogwarts. There are no murder mysteries, no magical silver bells, no Chocolate Frogs. You won’t meet James Bond or Santa Claus, though you may encounter a few old men who look like Horace Slughorn. And as you move between cars, you often pass someone who smells like they’ve been on the train for too long. But the Southwest Chief does boast something the others don’t — a spectacular observation car, complete with skylights, a snack bar, and couch-like seats facing the large windows.

When we arrived for breakfast, we were lucky to find a place to sit. Passengers crowded the car, eyes glued to the wide windows. Nick Carraway would have been thrilled. We chugged through curvy mountain passes that snaked down the back of the Rockies, often slowing to a hiker’s pace. We stopped at sleepy villages with names like Lamar, La Junta and Raton. As we began our descent into New Mexico, slabs of red rock peeked out at us beneath the blanket of white. By afternoon, the terrain had leveled off, and we were speeding through an endless expanse of scrubgrass that sprouted like stubble from the snowy ground. We passed more small towns. Trailers dotted the outskirts, clusters of burnt-out automobile carcasses collecting around them like metal shavings drawn to dingy, yellowing magnets.

Near Lamy, N.M., a white-haired woman with a “Mayflower Tours” name-tag that read “Pat” sat down next to me. I introduced myself and asked where she was headed.

“We’re getting off at Flagstaff and taking the train down to Nevada,” Pat said. “It’s just five of us old ladies — senior citizens, excuse me. I took this train down from Chicago 25 years ago, and I wanted to do it again. At least last time all the bathrooms worked.”

When I told her that I was searching for a trace of the great romantic cross-country train experience as detailed by Nick Carraway in The Great Gatsby, she seemed confused.

“You might find that on the Internet,” she said. “I don’t know much about the Internet.”

One of her companions tapped her on the shoulder.

“Pat, time for dinner.”

Pat apologized and shuffled off toward the dining car.


To me, this is a lot of nothing,” said Amy, the mother of the now-docile Little Miss Los Angeles, whom we had just officially met. She and her family were taking the train from Kansas City to Los Angeles because she had a fear of flying.

“It’s a lot of something … just something annoying,” said Chris, her husband, who had introduced himself as the owner of a company that made embalming fluids.

“So what sort of reaction do you usually get when you tell people about your profession?” Julien asked. Amy laughed.

“He’s not actually in embalming,” she said. “He composes music for cartoon shows. But he really likes to get a rise out of people. Sometimes we’ll be standing in a crowded elevator and he’ll say something like, ‘Hey honey, did you pick up your yeast infection meds today?’ I just fire right back and say ‘Yep — have you found your hemorrhoid cream?’”

We laughed. The conductor came by and told us our dinner table was ready. The train rolled through Albuquerque.


After a surprisingly elegant steak dinner in the dining car, Julien, Adrien, Kateri and I returned to the observation car. We sat down and started chatting with two men named Alvin and Gary. Both were middle-aged and black; Gary was a public school administrator from Los Angeles and Alvin was an off-duty Amtrak engineer who usually drove trains on the New York to Washington, D.C. route. I asked him why he was taking the train on his vacation.

“Cause it’s free,” he said, laughing. “Free for me and everyone in my family. So I’m headed Phoenix, transferring at Flagstaff. It’s a great job, pays about $80,000 a year. Only problem is the jumpers.”

“Jumpers?” asked Kateri.

“Yeah, sometimes people jump in front of the train to commit suicide,” said Alvin, whose name has been changed to protect his identity. “First time I saw it was in 2001. A hobo just dove right onto the tracks. I stopped the train — there were body parts everywhere. It was terrible.”

“What’s Amtrak’s policy on that?” I asked.

“If you hit someone, you’re just supposed to keep going,” Alvin said. “Passengers come first. Don’t get behind schedule. I got into a lot of trouble for stopping.”

We talked with Alvin and Gary for another hour. Over the course of the conversation, we discovered that Alvin spent most of his free time caring for foster children, was deeply homophobic and had a brain tumor. We spent a long time trying to convince him that he shouldn’t kick his foster children out of his house if he caught them fooling around with a member of the same sex. The Amish couple sitting a few tables down from us chuckled audibly at various points in the conversation, but left when we started talking about anal sex. Finally, the conductor announced that Flagstaff was coming up in fifteen minutes, and Alvin prepared to leave. He shook our hands, said he was glad to hear what the young generation was thinking and walked back to his sleeper car to get his bags. I thought that maybe we had moved him to start reconsidering his opinions on sexuality. But ten minutes later, he passed us again and acted as if he’d never seen us before. Gary, who hadn’t said much over the course of the conversation, got up to go check on him. When Gary returned five minutes later, he told us that Alvin’s brain tumor had caused him to lose his short-term memory. Gary had notified the conductor, and the two made sure that Alvin was able to leave the train at Flagstaff.

Before we left to go back to our seats and sleep, I asked Gary some rambling question about Nick Carraway and the romance of the cross-country train ride.

“Man, I don’t know about that one,” he said with a laugh. “Maybe the folks on the last train could have given you an answer — I think they were doing crystal meth.”

The next morning I awoke to find that we were already in Los Angeles. I began to feel a strange elation as we zipped along the palm tree-lined freeways clotted with morning traffic. When the four of us finally stepped off the train and wandered into the bright morning, I stretched my arms toward the sun — my own green light at the end of the dock.


Today’s Amtrak trains carry a vastly different group of passengers than those of Carraway’s day. Once the mode of long-distance transport favored by the wealthy, cross-country trains have become the realm of a very different cast of characters. College students, international tourists, elderly vacationers, people with a fear of flying, Amish who are willing to bend the rules and folks looking to avoid airline background checks are just a small cross-section of this motley crew.

For centuries, writers have quested after “America,” searching for a way of defining a country and a people through a single experience. Fitzgerald’s Carraway believed that a train ride could capture the spirit of a nation in some elemental way. Indeed, today’s cross-country train ride does capture something essentially American. But in contrast to Carraway’s journeys, that definitive aspect is not the physical landscape, but the bizarre, ordinary, and amazing people on the train. Boundaries of class, race, and gender dissolve along with state lines and time zones. And at the end of the evening, no matter what sort of green light a train-rider pursues, each passenger must return to the same creaky, back-cramping seats.

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Zack O'Malley Greenburg is the senior editor of media & entertainment at Forbes and author of two books: Michael Jackson, Inc and the Jay Z biography Empire State of Mind. In a decade at Forbes, Zack has investigated topics from pension fund scandals to Katy Perry's touring business to Wu-Tang Clan's secret album. His work has also appeared in the Washington Post, Billboard, Sports Illustrated, McSweeney's and Vibe; he's served as an expert source for BBC, NPR, MTV, NY Times and 60 Minutes, and as a speaker at SXSW, TEDx, Georgetown, Harvard and Yale, his alma mater. A recovering child actor, he played the title role in film Lorenzo's Oil (1992). Zack is now writing a new book, THREE KINGS, which will be published in 2017 by Little, Brown. Get Zack's quarterly email updates | Full bio

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