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Nostalgia, Loss, Discovery and Adventure around Jack Karouac's "On the Road"

ON THE ROAD by Jack Kerouac (1957)


On the Road, first published in the USA in 1957, is the most famous of Jack Kerouac’s many novels. It is semi-autobiographical, and is based on events that took place in the USA in the late 1940s and early 1950s. This is when Jack Kerouac (Sal Paradise in On the Road) and his friend Neal Cassady (Dean Moriarty in the novel) traveled throughout America, covering huge distances in a very short time. The story begins with Sal meeting Dean when he comes to New York for the first time. They discuss traveling to the west of the US, or “going West”. At first, Sal goes traveling on his own. He goes to San Francisco, staying with friends on the way there and falling in love on the way back. He and Dean do not travel together until some time later, going from the East to the West of the US and back again by car. Their adventures on the road involve meetings with girls, wild parties, getting drunk, taking drugs and enjoying sex. They never have much money and have to rely on delivering cars for people who don’t want to drive long distances themselves, doing casual work when they can, and sometimes stealing food, drink, and gas. The loosely-structured writing style and the freedom of the behavior and lives of the young people involved captured the attention of the public at the time. On the Road has remained a cult classic.


Jack Kerouac lived a brief but full life. He was born in 1922 and died in 1969 at the age of only 47. He was born into a family with French-Canadian roots, and did not speak English until he was six years old. It wasn’t long before he decided he wanted to be a writer. He started at the age of ten, writing a sports news sheet, and by eleven had written a complete novel. After leaving Columbia University in New York early - he had gone there as a football scholar, but his success was not helped when he broke a leg - Kerouac joined the Marines for the latter part of World War 2. He then took a succession of jobs while trying to make a living as a writer. By this time he had already decided he wanted to travel, and in writing On the Road he combined his desire to travel with his desire to write. Despite writing some thirty published and unpublished books, including plays and poetry as well as novels, Kerouac never repeated the international success of On the Road. This may have been because subsequent novels such as Doctor Sax (1959) and Big Sur (1962) repeated the themes of On the Road, and he found it impossible to, or he didn’t want to, develop into other areas. Kerouac’s style was spontaneous and unconventional, and it was this as much as the content that caused On the Road to be so well received. After his travels in the 1940s and 50s, Kerouac sought a more solitary existence in the 1960s. Dependent to some extent on alcohol and drugs throughout his life, he drank more and more.


Four men who met at Columbia University, New York, in 1946 were to become firm friends and fellow travelers through life. Indeed, they are all characters in On the Road. They were the writers Jack Kerouac and William Burroughs, the poet Allen Ginsberg, all three students at the University, and a wild young man who was on a visit there, Neal Cassady. They became key figures in an American social and literary movement known as the “Beat Generation”. It was Kerouac who invented the term “Beat”, which comes from the word “beatitude” (blessedness). The Beats, or Beatniks, expressed a mood that was common among young artists in the USA after World War 2: a mood of anxiety and anger, of rootlessness, and of disillusionment with the “American Dream” and society at large. They were perhaps the first literary group of “angry young men”, of rebels who led the way for later movements of artists expressing anger and dissatisfaction with the way society was - protest singers, hippies, the anti-Vietnam war peace movement, and punks. Their work encouraged young people to question rather than accept the values they were taught by their parents and teachers. They saw this not as a destructive influence but as something very positive. When Kerouac traveled he was looking for a positive experience, and wanted to find and describe the pure beauty of America, and the beauty of the “ordinary people” who inhabited it. The Beat Generation’s unconventional views of life were reflected in their appearance and behavior. Life for them was certainly not about conforming, it was about being on the road, listening to jazz (a huge influence on their literary style with its free forms and spontaneity), having wild parties, being alive, and living for the moment. Also, of course, life was about writing - not necessarily poetry or prose as such, but writing thoughts and feelings. These thoughts and feelings were also influenced by the Eastern religion of Buddhism, followed in particular by Kerouac and Ginsberg, which it is necessary to understand in order to fully appreciate the Beats themselves. Those four men who met at Columbia University in New York over seventy years ago remain cult heroes to this day, much admired by many with an “alternative” lifestyle. Cassady had a huge influence on Kerouac’s literary style, as Kerouac tried to use the same forms as Cassady did when he spoke, without hesitation or self-consciousness, and this led to the free-flowing letter writing style which became Kerouac’s trademark.


PART 1 – CHAPTER 1 - How It All Be

What you could call my life on the road began when I first met Dean Moriarty, not long after my wife and I separated. Before that, I often dreamed of going West to see the country, always planning but never going. Dean is the perfect guy for the road because he was actually born on the road, when his parents were passing through Salt Lake City in 1926, on their way to Los Angeles. First reports of him came to me through Chad King. Chad showed me some letters from Dean, written in a New Mexico jail for kids. This is all far back, when Dean was not the way he is today, when he was just a mysterious jail-kid. Then news came that Dean was out of jail and was coming to New York for the first time; also there was talk that he had just married a girl called Marylou.

One day in college Chad and Tim Gray told me Dean was staying in rooms in East Harlem. He had arrived the night before with beautiful little Marylou. They got off the Greyhound bus at 50th Street, went around the corner to Hector's cafe and bought beautiful big cream cakes. All the time, Dean was telling Marylou things like: "Now, darling, here we are in New York and although I haven't quite told you everything I was thinking when we crossed the Missouri River, it's absolutely necessary now to postpone all those things concerning our personal love, and at once begin thinking of work-life plans ... " That was the way he talked in those early days.

I went to their little apartment with the boys, and Dean came to the door in his shorts. Dean had blue eyes, and a real Oklahoma accent. He had worked on Ed Wall's farm in Colorado before he married Marylou. She was a pretty blonde, with long curly hair. She sat on the couch, her smoky blue eyes staring. But although she was a sweet little girl, she was stupid and could do horrible things. That night we drank beer and talked until dawn, and in the morning while we sat around smoking in the gray light of a gloomy day, Dean got up nervously, and walked around, thinking. Then he decided Marylou could get some breakfast. Later, I went away.

During the next week, he told Chad King that he absolutely had to learn how to write; Chad said that I was a writer and he should come to me for advice. Then Dean had a fight with Marylou in their Hoboken apartment just across the Hudson River from New York and she was so angry that she went to the police and accused Dean of some false, crazy thing so that Dean had to run away from Hoboken. He came right out to Paterson, New Jersey, where I was living with my aunt, and one night while I was studying there was a knock on the door.

And there was Dean in the dark hall, saying, "Hello, you remember me — Dean Moriarty? I've come to ask you to show me how to write."

"And where's Marylou?" I asked. And Dean said that she had gone back to Denver. So we went out to have a few beers because we couldn't talk like we wanted to talk in front of my aunt, who took one look at Dean and decided that he was a mad man. In the bar I told Dean, "You didn't come to me only to learn to be a writer, and anyway what do I really know about it except that you have to work and work at it."

And he said, "Yes, of course, I know exactly what you mean and in fact all those problems have come to my attention, and ... " and on and on about things I didn't understand, and he didn't either. But we understood each other on other levels of madness, and I agreed that he could stay at my house till he found a job. And we agreed to go out West at some time. That was the winter of 1947. One night we went to New York, and it was the night that Dean met Carlo Marx. They liked each other immediately, and from that moment on I did not see Dean as often as before. And I was a little sorry too.

But all the crazy things that were going to happen began then. It would mix up all my friends, and all I had left of my family, in a big dust cloud over the American Night. Carlo told Dean of Old Bull Lee, Elmer Hassel, Jane: Lee in Texas growing marijuana, Hassel in jail, Jane wandering on Times Square, full of drugs, with her baby girl in her arms, until somebody took her to Bellevue Hospital. And Dean told Carlo about people in the West like Tommy Snark, the card player, Big Ed Dunkel, his many girlfriends, sex parties, and other adventures.

Then the spring came, the great time of traveling, and everybody was getting ready to go on one trip or another. I was busy working on my novel. And when I was halfway, and after a trip down South with my aunt to visit my brother Rocco, I got ready to travel West for the very first time.

Dean left before me. Carlo and I went with him to the 34th Street Greyhound bus station. Dean was wearing a real Western business suit for his big trip back to Denver. It was blue, and he bought it in a store on Third Avenue for eleven dollars. He also had a small typewriter, and he said he was going to start writing as soon as he got a job and a room in Denver. We had a last meal together, then Dean got on a bus which said Chicago and went off into the night. I promised myself to go the same way soon.

And this was really the way that my whole road experience began, and the things that happened were amazing, and must be told.


The end of our journey impended. Great fields stretched on both sides of us; a noble wind blew across the occasional immense tree groves and over old missions turning salmon pink in the late sun. The clouds were close and huge and rose. "Mexico City by dusk!" We'd made it, a total of nineteen hundred miles from the afternoon yards of Denver to these vast and Biblical areas of the world, and now we were about to reach the end of the road. "Shall we change our insect T-shirts?" "Naw, let's wear them into town, hell's bells." And we drove into Mexico City. A brief mountain pass took us suddenly to a height from which we saw all of Mexico City stretched out in its volcanic crater below and spewing city smokes and early dusk lights. Down to it we zoomed, down Insurgentes Boulevard, straight toward the heart of town at Reforma. Kids played soccer in enormous sad fields and threw up dust. Taxi-drivers overtook us and wanted to know if we wanted girls. No, we didn't want girls now. Long, ragged adobe slums stretched out on the plain; we saw lonely figures in the dimming alleys. Soon night would come. Then the city roared in and suddenly we were passing crowded cafes and theaters and many lights. Newsboys yelled at us. Mechanics slouched by, barefoot, with wrenches and rags. Mad barefoot Indian drivers cut across us and surrounded us and tooted and made frantic traffic. The noise was incredible. No mufflers are used on Mexican cars. Horns are batted with glee continual. "Whee!" yelled Dean, "Look out!" He staggered the car through the traffic and played with everybody. He drove like an Indian. He got on a circular glorietta drive on Reforma Boulevard and rolled around it with its eight spokes shooting cars at us from all directions, left, right, izquierda, dead ahead, and yelled and jumped with joy. "This is traffic I've always dreamed of' Everybody goes.'


In downtown Mexico City thousands of hipsters in floppy straw hats and long-lapeled jackets over bare chests padded along the main drag, some of them selling crucifixes and weed in the alleys, some of them kneeling in beat chapels next to Mexican burlesque shows in sheds. Some alleys were rubble, with open sewers, and little doors led to closet-size bars stuck in adobe walls. You had to jump over a ditch to get your drink, and in the bottom of the ditch was the ancient lake of the Aztec. You came out of the bar with your back to the wall and edged back to the street. They served coffee mixed with rum and nutmeg. Mambo blared from everywhere. Hundreds of whores lined themselves along the dark and narrow streets and their sorrowful eyes gleamed at us in the night. We wandered in a frenzy and a dream. We ate beautiful steaks for forty-eight cents in a strange tiled Mexican cafeteria with generations of marimba musicians standing at one immense marimba-also wandering singing guitarists, and old men on corners blowing trumpets


What difference can you notice between the first and the second chapter above?

Is the writing style the same?

How has it changed and how has the writer changed, after his travels "on the road"?

The story of the travels of Sal Paradise and his friends takes place in the USA in the late 1940s. Discuss how their experiences would be different if they traveled across the USA in the late 2010s. Think about: cars, public transport, hitch-hiking, money, casual labor, popular music, and the attitudes of society.


On the Road” first appeared in 1957. Why do you think it is still popular?

Do the characters in the book share any sense of right and wrong? Give reasons for your opinions. Would you like them as your friend?

Some people say that On the Road is about a journey of self discovery. In what ways do you think this is true?

What kind of traveler are you?



1) Bob Dylan's "Fare Thee Well" (1963) questioning Time, Loss, Nostalgia, Distance...


Oh it's fare thee well my darlin' true, I'm leavin' in the first hour of the morn. I'm bound off for the bay of Mexico Or maybe the coast of Californ’. So it's fare thee well my own true love, We'll meet another day, another time. It ain't the leavin' That's a-grievin' me But my true love who's bound to stay behind.

Oh the weather is against me and the wind blows hard And the rain she's a-turnin' into hail. I still might strike it lucky on a highway goin' west, Though I'm travelin' on a path beaten trail. So it's fare thee well my own true love, We'll meet another day, another time. It ain't the leavin' That's a-grievin' me But my true love who's bound to stay behind.

I will write you a letter from time to time, As I'm ramblin' you can travel with me too. With my head, my heart and my hands, my love, I will send what I learn back home to you. So it's fare thee well my own true love, We'll meet another day, another time. It ain't the leavin' That's a-grievin' me But my true love who's bound to stay behind.

I will tell you of the laughter and of troubles, Be them somebody else's or my own. With my hands in my pockets and my coat collar high, I will travel unnoticed and unknown. So it's fare thee well my own true love, We'll meet another day, another time. It ain't the leavin' That's a-grievin' me But my true love who's bound to stay behind.

I've heard tell of a town where I might as well be bound, It's down around the old Mexican plains. They say that the people are all friendly there And all they ask of you is your name. So it's fare thee well my own true love, We'll meet another day, another time. It ain't the leavin' That's a-grievin' me But my true love who's bound to stay behind.

2) Willie Nelson's "On the Road Again" (1980) is instead about Space, Distance, Friendship, People, Happiness


On the road again Just can't wait to get on the road again The life I love is making music with my friends

And I can't wait to get on the road again

On the road again Goin' places that I've never been Seein' things that I may never see again And I can't wait to get on the road again

On the road again Like a band of gypsies we go down the highway We're the best of friends Insisting that the world keep turning our way And our way

Is on the road again I just can't wait to get on the road again The life I love is makin' music with my friends And I can't wait to get on the road again

On the road again Like a band of gypsies we go down the highway We're the best of friends Insisting that the world keep turning our way And our way

Is on the road again Just can't wait to get on the road again The life I love is makin' music with my friends And I can't wait to get on the road again And I can't wait to get on the road again


Nostalgia, Loss, Discovery, Adventure, Holiday, Friendship, Experiences

Riccardo Zambon


Rovigo, 19th February 2022

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