Study Guide

On the Road Analysis

By Jack Kerouac

  • Tone

    Retrospective, Thoughtful, Sad

    It’s pretty amazing how a book that’s so much fun to read ends up making you want to sit in a beach and stare into the water and contemplate the subtleties of your life. Which is what it sounds like Kerouac is doing in this book. Sal, the narrator, is straightforward about what happens, but he’s also incredibly reflective about it afterwards. He realizes that his hero, Dean, is a rat, or he stops to think about Rickey’s foolish mantra, or he wonders at the transience of the friendships he forms on the road. All of these reflective bits are a little sad. It’s easy to forget this when you get caught up in the sex and the stories and the intoxication of the language – but it’s there.

  • Genre

    Literary Fiction

    On the Road can’t really be categorized as tragedy or comedy or any of your normal genre subdivisions. "Frantic-poetry-like-tale," perhaps, but we couldn’t find that section in Barnes and Noble.

  • What’s Up With the Title?

    Main character Sal Paradise spends about, oh, let’s see…99.9% of his time traveling on the road. And the other 0.1% of the time he’s wishing he could be on the road. On the surface, the title describes exactly what’s going on, but if you want to get all English-majory (which we feel like doing about once a week), you could say it also describes Sal’s ethos and the ethos of the whole Beat Generation that Kerouac represents with this book: their restlessness, dissatisfaction, longing for something and somewhere else.

  • Setting

    America and Mexico in the 1940s and 1950s, specifically New York, Chicago, Denver, San Francisco, and Mexico City

    To discuss the "setting" of On the Road is interesting and informative about just what’s going on in this text. Sal is restlessness, right? He keeps needing to move, to go somewhere else – but we really only see him in four major American cities – New York, Chicago, Denver, and San Francisco – each of which takes on a persona and describes a particular phase on Sal’s travels.

    The temporal setting is a post World War II America, a time that Sal and his friends find full of intellectual falsity (read: the arty types "sucking up the blood of America") and in fact rather aimless. There is a need to go, to be, to do something, but this Beat Generation, defined by its time and circumstance (i.e., the setting), doesn’t know where or how to channel that energy.

  • Writing Style

    2 Fast, 2 Furious

    And we're not just calling it that because a lot of On the Road takes place in cars. More than most, Jack Kerouac was famous for crystalizing the Beat style of writing with his work. What's the Beat style, you ask?

    Well, dig it daddy-o's and hep gals, allow Shmoop to enlighten you. The Beats shared a philosophy that privileged spontaneity, non-conformity, and, well, self-indulgence. At the core of their beliefs, though, was a kind of ecstatic embrace of the world and every possibility that might lie in it. Now, what does that look like in a writing style?

    Well, think about how you might sound if you were ecstatic about something, just really amped up about something. Maybe you've just pulled off the most rad BMX trick ever. Or maybe you just skydived for the first time. Or maybe you cured cancer. Now a reporter comes running over to you to ask you about it. How are you gonna sound?

    One way to answer that question is by reading On the Road. It's just brimming with wild energy, with sentences that rush across the page, taking turns left and right, before coming to an exhausted stop. Then, the next crazy train of a sentence takes off. Here's a sample of what we mean:

    I went to the cold-water flat with the boys, and Dean came to the door in his shorts. Marylou was jumping off the couch; Dean had dispatched the occupant of the apartment to the kitchen, probably to make coffee, while he proceeded with his loveproblems, for to him sex was the one and only holy and important thing in life, although he had to sweat and curse to make a living and so on. You saw that in the way he stood bobbing his head, always looking down, nodding, like a boxer to instructions, to make you think he was listening to every word, throwing in a thousand "Yeses" and "That's rights." My first impression of Dean was of a young Gene Autry – trim, thin-hipped, blue-eyed, with a real Oklahoma accent – a sideburned hero of the snowy West. In fact he'd just been working on a ranch, Ed Wall's in Colorado, before marrying Marylou and coming East. Marylou was a pretty blonde with immense ringlets of hair like a sea of golden tresses; she sat there on the edge of the couch with her hands hanging in her lap and her smoky blue country eyes fixed in a wide stare because she was in an evil gray New York pad that she'd heard about back West, and waiting like a longbodied emaciated Modigliani surrealist woman in a serious room. But, outside of being a sweet little girl, she was awfully dumb and capable of doing horrible things. That night we all drank beer and pulled wrists and talked till dawn, and in the morning, while we sat around dumbly smoking butts from ashtrays in the gray light of a gloomy day, Dean got up nervously, paced around, thinking, and decided the thing to do was to have Marylou make breakfast and sweep the floor. "In other words we've got to get on the ball, darling, what I'm saying, otherwise it'll be fluctuating and lack of true knowledge or crystallization of our plans." Then I went away. (1.4)

    Okay, all together now: DEEP BREATH. Whew! That is one rambling paragraph, meandering from point to point with plenty of sidetrips in between. Sound familiar?

    It should. The speed and wandering energy of the writing style is mirrored perfectly by the rambling journey of the novel's characters, which, in turn, are totally in keeping with how the Beats lived their lives on a personal level. Still, we invite you to see this as a kind of controlled chaos, not just a series of random events or word choices. Underlying all this motion was a restlessness to experience the next big thing, and an eagerness to experience it in a hurry.

  • Symbolism, Imagery, Allegory

    The Cadillac

    Dean and Sal drive a Cadillac across country to Chicago. Or rather, they start with a Cadillac, and they end up with a big hunk of destroyed metal. What destroys this car, you ask? Primarily, it’s Dean – Dean’s mad, fast driving, his need to move, and his dangerous lifestyle. Now for the symbolism. The Cadillac is an American car, and a big beautiful Cadillac is all tied up with the Big Beautiful American Dream. The Beat Generation is running around rebelling against the American Dream, and destroying in it their trips across country with their mad, fast driving, their need to move, and their dangerous lifestyles. Ohhhh.

    Times Square

    Every time Sal returns to New York, he goes back to Times Square. Now you might have noticed a slightly obsessive discussion of time that permeates this novel. Time…Times Square…Time. Let’s give it a shot. Dean measures everything in terms of time, right? This many minutes for sleeping with Camille, this many hours for driving to Chicago, etc. And Sal, Sal always measures things in distance. He’s 2,000 miles from home, or there’s 50 miles left to Denver, and so on. Sal isn’t as conscious of time as Dean, until he returns to New York and looks out over "those awful cemetery cities beyond Long Island City" and realizes everyone’s going to die. So while he’s right back where he started geographically (New York), he realizes that TIME is running out. Because Sal thinks in terms of places, he needs a physical location to represent time, like Times Square.


    Check out Sal pawning his watch for gas on the way to Tucson. It’s a four dollar watch, he tells us, so naturally he sold it for one dollar. Sal drastically undervalues time. Not to mention, he sells the watch for gas money, which means he’s trading time for distance. Not unlike using years and years to travel across the country.

    Young Girls

    Wait a minute – Dean’s lusting after young girls is pedophilia, not a symbol. Right? Well, depends on how literary you’re feeling. Dean thinks in terms of time, and the problem with time is that it makes us all older. We were particularly interested in that passage where Dean and Sal play basketball against some younger boys and we get to see that Dean and Sal are aging. So what’s a frantic, older man to do? Fall in love with youth. And the nearest embodiment is youth is a very young girl, or two, or twelve, that Dean lusts after.


    Not the Stephen King novel, either. By "IT" we mean…well, what do we mean? That’s the question. Only it’s more like, what is Dean talking about with this IT business? Does he even know? And what is going on with this flagrant abuse of capital letters?

    Dean tends to talk about IT when he’s talking about 1) time and 2) God. So IT has something to do with time and God. Also it’s capitalized, so that you don’t mistake IT for a pronoun when you’re reading. So it’s important; we get that. But what does it mean? IT becomes this thing that Dean seeks and then knows, insists that Sal knows, but won’t detail explicitly because he just doesn’t have the time. Musicians have IT, George Shearing definitely has IT, and because of IT, Dean is able to groove anywhere in America.

    IT most likely is to Dean what this "pearl of wisdom" business is to Sal. It’s the end of the road. It’s what they’re searching for. But the problem with the Beat Generation was that they didn't know what they wanted. There’s a reason that IT is vague, and it’s because the desires of the Beat Generation were vague. That’s what makes their dissatisfaction so frustrating. Dean simply put a name on this thing that he doesn’t know he wants; he calls it IT.

  • Narrator Point of View

    First Person (Central Narrator)

    We see the story through the eyes of Sal Paradise, the character who is supposed to mirror Jack Kerouac himself. What’s interesting is the other main character, Dean Moriarty. Sal is, to a degree, slightly obsessed with Dean and focuses on this quite a bit. Sal remains our main character, though. We see his thoughts, not Dean’s, get his background, see him live and talk without Dean there.

    Sal’s perspective let’s us hear On the Road as if it’s just another story being told by some truck driver to the hitchhiker he picked up (yes, in this analogy, you are the hitchhiker). Which is cool. It’s colored with some looking-back perspective because of the first person narration, and so we get a bit of insight into the characters that we might otherwise miss.

  • Booker's Seven Basic Plots Analysis

    This novel doesn't quite fit the Booker framework because it's more like Voyage and Return, and voyage. And return. And then voyage, return, followed by some voyage, and remarkably, a return.

  • Plot Analysis

    On the Road is famous for not following a standard plot. In fact, it’s famous for doing a horrible job at being a novel, in the plot sense of what a novel should be. This may have something to do with the fact that Kerouac banged out a manuscript in a few weeks on one long piece of typewriter paper. But, because we were feeling experimental, we decided to give it a shot anyway. Let us know if it works for you.

    Initial Situation

    The part where On the Road doesn’t fit the Classic Plot structure so well.

    The first sentence of On the Road is the conflict, so there isn’t so much of an initial situation.


    "I first met Dean Moriarty" etc.

    Yes, that’s right: Dean is the conflict. Dean either causes Sal’s restlessness or incites some latent restlessness. It is in large part due to Dean that Sal takes off across the country. Dean also sets up the conflict inherent in any relationship in which one guy idolizes another: eventually, Dean has to become human in Sal's eyes.


    All of the novel until Mexico, which in itself is kind of complicated.

    Basically all of On the Road is complication after complication, through which we come to better understand our narrator and his hero. The poverty, the women, the policemen, the thefts – all of these serve as complications in the story’s plot.


    The alcohol/drug/prostitute blowout in Mexico

    Sal and Dean have spent the entire novel in pursuit of "the end of the road." They believe they will find it in Mexico, and do in fact declare parts of the country "heaven" when they get there. This is also the climax of drug and alcohol use, as well as the climax of Sal’s idolatry of Dean, since he finally calls his hero "God."


    Sal gets a fever in Mexico! Will he survive? Dum dum dum…

    The suspense lies not only in the fact that Sal might die, but that his friendship and idolatry of Dean is brought into question. Dean betrays his friend big-time here, leaving Sal in Mexico on what could be his deathbed. Sal says he’ll "say nothing," but we don’t know if he genuinely forgives Dean. Even if he does, it could still be that his conception of Dean has been forever ruined.


    Sal finally finds The Girl, and Dean makes a last visit.

    Sal’s grand search for love in America is over. We know this is denouement material and not climax material because this woman (Laura) is presented in such an understated way. No fireworks, just a simple declaration that she’s the one. Dean’s final visit, too, lacks the vitality and energy of previous interactions we’ve seen between our two main characters. If the novel is winding down, so is Sal – and whether he likes it or not, so is Dean.


    Sal ruminates on the world and Dean.

    Sal ends, not surprisingly, on a note of sadness. He wonders at the fact that Dean came all the way to New York just to see him, and realizes that he could not help his hero in the end. Dean is still clearly with him, though, still the focus of Sal’s thoughts.

  • Three Act Plot Analysis

    Act I

    The Sal and Dean saga begins, with idolatry in Denver, followed by some time with Remi Boncoeur in San Francisco, and some Terry goings-on thrown in for good measure.

    Act II

    The second cross country trip, with excessive drug use (Bull Lee in New Orleans) and the first notions of blatant abandonment in San Francisco. Act II would end with the Cadillac trip to Chicago before the return, once again, to New York.

    Act III

    The journey to magic South, i.e., Mexico. This act includes many revelations, a deeper look into Dean’s character, and a thought-provoking conclusion on the streets of New York.

  • Allusions

    Literature, Philosophy, and Mythology

    Sir Arthur Conan Doyle: Sherlock Holmes (Dean’s last name, ‘Moriarty’).
    Karl Marx (Carlo’s name)
    Frederick Nietzsche (I.1.1, II.3.11)
    Arthur Schopenhauer (I.1.7)
    Johann Wolfgang von Goethe (I.1.12, I.6.6)
    George Ruxton: Life in the Far West (I.6.1)
    Arthur Rimbaud (I.7.10)
    Opera Fidelio (I.9.6, I.9.16)
    Jack London (I.11.73)
    Ecclesiastes (I.1.16)
    Allen Ginsberg: Denver Doldrums (I.7.23, I.8.7, II.3.5)
    Ernest Hemingway (I.7.1, I.9.10, I.104): Green Hills of Africa (I.10.12), The Sun Also Rises (I.11.101-I.11.104)
    Fyodor Dostoevsky (I.11.51)
    Alain-Fournier: Le Grand Meaulnes (I.14.1)
    The Bible (II.6.17, IV.2.2): Solomon (II.6.17)
    Shakespeare (II.6.38)
    Maya Codices (II.6.34, II.6.35)
    Kafka (II.6.54)
    Eugene Sue: Mysteries of Paris (III.2.16, III.3.4)
    Sir Thomas Aquinas, (III.8.16)
    Herman Melville: Moby Dick (III.9.16)
    Louis-Ferdinand Céline (II.6.10)
    Marcel Proust (V.5)

    Historical Figures

    President Truman (I.11.63, I.11.65, I.11.70, II.6.4)
    Mickey Cohen (III.9.12)
    Stonewall Jackson (IV.2.1)
    Franklin Delano Roosevelt (IV.5.39)

    Music and Movies

    James Dean (Dean’s first name)
    Gene Autry (I.1.4)
    Jack Dempsey (I.4.50)
    Beethoven (I.9.6)
    Sullivan’s Travels (I.12.14)
    Veronica Lake (I.12.14)
    Joel McCrea (I.12.14)
    George Murphy (I.13.3)
    Lionel Hampton: "Central Avenue Breakdown" (I.13.5)
    Of Mice and Men (the movie) (I.13.11)
    Burgess Meredith (I.13.11)
    Billie Holiday (III.4.4): "Lover man" (I.13.46)
    Peggy Lee: "Mañana Is Soon Enough For Me" (I.13.49)
    Irving Berlin: "Blue Skies" (I.13.50)
    Dexter Gordon and Wardell Gray: "The Hunt" (II.1.15, II.4.15).
    Groucho Marx (II.3.11, II.4.15, II.7.15, III.4.14)
    W.C. Fields (I.7.1, II.3.11, II.6.36, IV.4.6)
    Giuseppe Verdi (II.4.15)
    George Shearing (II.4.18, II.10.9)
    Dizzie Gillespie (III.7.11, III.10.4)
    Lester Young (musician) (III.10.3, III.10.4, IV.1.2)
    Charlie Parker (I.3.2, III.10.3, III.10.4)
    Miles Davis (I.3.2, III.10.3)
    Louis Armstrong (III.10.4)
    Roy Eldridge (III.10.4)
    Count Basie (III.10.4)
    Benny Moten (III.10.4)
    Thenolius Monk (III.10.4)
    Willie Jackson (IV.1.2)
    Stan Getz (IV.I.18)
    Gary Cooper (IV.2.16)
    Wynonie Harris (IV.4.9)
    Lionel Hampton (IV.4.9)
    Lucky Millinder (IV.4.9)
    Duke Ellington (V.13)


    Amadeo Modigliani (I.1.4)
    Rembrandt (I.9.6)


    Don Ameche (I.13.3)
    Marty Glick (IV.1.2)
    Gil Hodges (IV.I.17)
    Joe DiMaggio (IV.I.17)
    Bobby Thomson (IV.I.17)