On the Road by Jack Kerouac [A Review]

When Jack Kerouac’s On the Road was first published in 1957 it was soon recognised as a modern classic. Its influence has been widespread, has crossed generations and saw its author hailed as the voice of a generation. It has been described as innovative in its style, shocking in its frank depictions of sex and drugs, but romantic and spiritual in its character’s naïve quest for freedom and meaning. Yet it is common to hear readers say they could not stand reading it. With its difficult prose, unconventional plot, diluted themes, unlikeable characters and with many successful iterations of its themes made since; is there much reason left for the modern reader to read On the Road?

On the Road

Sal Paradise; divorced, barely employed, sometime student, attempted writer; lives in his aunt’s apartment in 1947 New Jersey feeling somewhat lost and uncertain. As the weather turns warmer and a summer breeze floats into Jersey and New York his mind turns eastward towards the wide free spaces of America. Somewhere out there is the answer to his life, a pearl of wisdom and enlightenment. Sal has been reading the epic, wild, ranting letters of one Dean Moriarty and within them sees a kindred spirit, another searcher. Sal feels he knows what he must do. He must hit the road and seek out Moriarty, to discover a real America, to search out pure joy and pleasure, perhaps even to find meaning for his life.

So begins Jack Kerouac’s On the Road with its immortal first paragraph line:

With the coming of Dean Moriarty began the part of my life you could call my life on the road.

In On the Road, we follow Sal and Dean as they cross the country over a few summers in the late 40’s; hitchhiking, riding the rails, trashing rental cars or even their own. They share stories with fellow travellers and journeymen, drink heavily each night, thrill to the sounds of jazz and beg, borrow and steal to keep the journey going.

On the Road is a novel often cited as defining a generation, changing lives and influencing many other searchers and writers. The novel catapulted the career of Kerouac who became a Cobain-like figure of the time; the media had less interest in his writing or his books than in his potential as a spokesman for a generation, which he never aspired or claimed to be. For a novel hailed as a hugely influential modern classic, it is strange then that so many readers confess that they cannot stand this book, many saying they could not finish it and some that they could barely even start it.

Within the first few pages the reason for this disdain becomes obvious; it is the prose. The style is a form of stream-of-consciousness but there are some differences. True stream-of-consciousness is wayward and distracted. Like a car being driven on a dark highway, feeling for the road, it tends to swerve onto the shoulder before overcorrecting and swerving onto the other shoulder. Overall it is still heading in the right direction but, for other considerations, taking far longer than necessary to get there. The prose of On the Road is no less spontaneous but its direction is more direct. It reads like Dean Moriarty’s driving – in straight lines on flat roads at 110 mph. As if it is being written by someone who has consumed a few more coffees than necessary to induce a cardiac arrest. Which is not too far from how it was written. Kerouac famously wrote On the Road over a three week period in 1951, on a 120 foot scroll of continuous paper he had constructed, without paragraph breaks, taking Benzedrine to stay awake. The prose style and the story of its composition prompting Truman Capote’s famous sneer: “That isn’t writing; it’s typing”.

But the prose style does achieve symbolic resonance within the story. As well as the high speeds of Moriarty’s driving, the prose style also complements Sal’s great love for jazz. Like jazz, the prose is rapid, spontaneous and bursting with creativity liberated from convention. The prose also complements the telling of Sal and Dean’s wayward drug taking and frequent bouts of heavy drinking.

Whether the originality of the style, or its fusion with the subject, is an outcome we can attribute to Kerouac’s intentions is another matter. Despite the apparent spontaneity of the novel’s creation story, the truth is that Kerouac had been attempting to write On the Road for quite some time, experimenting with different narrators and styles, sometimes even envisioning a great quixotic epic, and never getting far. His previous novel, The Town and the City, borrowed the style and structure of Tom Wolfe’s Look Homeward, Angel. Kerouac struggled to find a unique voice for his writing or even a fictional plot and characters for his idea of On the Road. Though he chided other writers for producing roman à clef’s, in the end that is just what Kerouac did here.

Drafted as it was from memories of real events, written in hasty frustration after a few abortive attempts where story and characters remained elusive, it is difficult to dismiss Capote’s criticism as anything other than apt. Kerouac’s innovation may be more incidental than inspired. As well as the prose, difficulties with the story and characters of the novel are also difficult to look past.

The novel clearly lacks a conventional plot structure and, while some may be inclined to give Kerouac credit for breaking with convention, I would say that it is an experiment that fails. In the absence of convention, Kerouac has not produced an endearing or intriguing story as a viable alternative. The novel reads as a series of recollections of the narrator’s trans-continental drinking trips, which it very much is. What story there is, is mainly contained in Parts 2 and 3. Part 1 feels unnecessary, its relevant passages could have been easily incorporated into Part 2. Part 4, containing a Mexican sojourn, almost feels like another novel and could have been best excluded. There are more issues with the plot I would like to discuss but they are difficult to do so without first discussing the equally difficult problems with the characters.

The character of Dean Moriarty, like all the characters in the novel, is based on a real person – Neal Cassady (pictured on the left of the book cover above, Kerouac is on the right). Cassady must have been quite a character to have bewitched the imagination of a number of writers. As well as being the basis of Dean Moriarty in On the Road (and other characters in Kerouac’s novels), he is also mentioned in some of Allen Ginsberg’s poems, including Howl; he also makes appearances in Hunter S Thompson’s Hells Angels, Tom Wolfe’s The Electric Kool-Aid Acid Test and has even been linked to McMurphy of Ken Kesey’s One Flew Over the Cuckoo’s Nest.

To have had such an impact on these talented writers, and through them a lasting impact on popular culture, Cassady must have been a very charismatic and beguiling character. Unfortunately, this impression does not reach the reader of On the Road. It is very difficult for the reader to share Sal’s fascination with Dean. Kerouac is never able to convince the reader that Dean is a new-age mystic; a searcher, or even a possessor, of some truth or secret to life’s meaning.

Instead Dean comes across as a man who knows how to pose a question, but is completely lost as to how to find an answer and never asks himself whether his question was meaningful to begin with. He can never follow through with his intentions and ambitions and as a result he can only inspire but never deliver. All that he is left with are the intellectual and spiritual pretensions of a false prophet.

Beyond Dean’s failing as a character of mystery, intrigue and charisma, he also fails to endear himself to the reader. By his actions, he does not search, he abandons. He abandons the women in his life, he abandons his jobs, he abandons all his responsibilities and not to find truth and meaning, but to drink, to drive fast, to party to jazz and to chase young girls. Despite his intellectual pretensions it is hard to see what he hopes to achieve by this but his own hedonistic selfish desires.

His taste in women make him particularly repugnant. Dean marries Marylou, a girl he first met when she was fifteen and he much older. Later in the story, even Sal feels he has to protect the thirteen year old daughter of a friend from Dean’s lascivious gaze. When they are in possession of a car, Dean seems to feel its best use would be to pick up high school girls half their age. At one point, Dean has to escape a mob after trying to pick up a teenage girl.

In fact, the voices of women are noticeably absent in the novel despite their constant presence. Marylou, for all the intrigue she has possessed for readers over the years, is given very little dialogue. She sports bruises from an argument with Dean. Sal too will hit her before long and, when low on money, Dean considers pimping her out.

“You see what a bastard he is”, said Marylou. “Dean will leave you out in the cold any time it’s in his interest”.

“I know”, I said and I looked back east and sighed.

It appears to the reader that to Sal, Dean and the other men who dominate the novel, women are possessions to be used for sex and their money. A woman who does not obey their view of them, becomes a ‘whore’. Otherwise, women are like jobs and responsibilities; a hassle, an anchor, that weighs you down and prevents you from following your desires and living free. The recent film adaptation of On the Road deliberately gave the female characters more of a voice so as to offset the misogynistic taint a faithful adaptation might otherwise have produced. Although Sal does share his wishes for a serious committed relationship, it is clear he does not know how to achieve this, behaving instead as if women need to be heavily persuaded or conned into liking him.

One minor character, Ed Dunkel, marries a woman, Galatea, ostensibly for her money to finance his and Dean’s trip across the country. When her money runs out, they ditch her in Arizona. We come across Galatea again later in the novel in an extraordinary passage where she calls out Dean for what he is.

“You have absolutely no regard for anybody but yourself and your damned kicks. All you think about is what’s hanging between your legs and how much money or fun you can get out of people and then you just throw them aside. Not only that but you’re silly about it. It never occurs to you that life is serious and there are people trying to make something decent out of it instead of just goofing off all the time”

That’s what Dean was, the HOLY GOOF.

This was by far my favourite part of the novel. I rejoiced at reading a character who saw Dean the way I saw him too. Though Sal tries to defend Dean, there are signs either side of this passage that their friendship is starting to fray. I hoped at this point in the reading that the novel would turn into a cautionary tale; that Sal would wake up from his deluded admiration for Dean, shake off his naïveté and grow as a person from the experience. But the novel does not really get there.

Which leaves us with the question of what this novel is about. Given the nature of its inspiration and writing it would seem a question as relevant as asking what any summer vacation was ‘about’.

I had hoped, in picking up the novel, that it would be about the romance and freedom of the open road, of the fulfilment to be found in journeys rather than destinations. But there is little to nothing of that to be found in the novel. Instead the characters race across the country with little thought as to their destination and at speeds that undermine any consideration for the journey. These trips are as fleeting and pointless as their binge drinking and drug taking. The freedom they seek has no staying power, but again the disillusionment such a realisation should bring never really arrives.

Stories about journeys are equally about what the characters are running away from as what they are heading towards. There are details in the novel of Dean’s past – one without family, frequently on the wrong side of the law, time spent in juvenile detention. There is a sense that, unlike Sal and other characters in the novel, Dean has been deprived of the same opportunities and so possesses unfulfilled potential. That Sal has spent time in the Army is also alluded to but never explored. It is difficult to argue that escapism from the psychological trauma of a troubled past is strong theme of the novel. Instead, the characters are escaping from their responsibilities which are of the ordinary everyday variety we all face. Observers who comment that Gen-Y and Millennials are reluctant to grow up ought to read On the Road and see that the phenomenon is nothing new. It could be argued that this novel is a story of grown men, in their late-20’s-early-30’s, who ditch their wives, girlfriends and jobs in order to drive fast, drink heavily and try to sleep with high-school-age girls.

The real Dean, Neal Cassady, died in 1968 aged just 41. The cause of death was most likely exposure as he had left a wedding party, where he had been taking drugs, and wandered through a rainy night wearing just a t-shirt and jeans until he passed out. The real Sal, Jack Kerouac, died the following year aged 47 from severe internal haemorrhaging as a result of years of heavy drinking. It sounds like a case of life imitating art imitating life.

It could be argued that by containing many socially unacceptable activities – the drinking, the drugs, the theft, fraud, abuse of trust, domestic violence, destruction of property, the sex (pre-marital, extra-marital and almost more) – means that the novel achieves a break in social convention and brings a hidden ‘real’ America to light. Though probably true, like the prose style and the plot, it is hard to argue that this was the intent of the author and not just a record of events Kerouac did and witnessed.

More credible is the claim that On the Road is an exposé into the American underground, albeit sparingly and without the depth you might expect from such a reputation. This insight comes more from some of the characters Dean and Sal meet on the road rather from Dean and Sal themselves. However, Sal’s journey into the underground does raise some questions for the modern reader. Sal, like his real-life double Kerouac, is not Beat himself and the Beats are not a community in the sense that Sal’s entries and exits from their world are noticeable from their point of view. Otherwise, it would be hard for the reader to find Sal’s acceptance by Beats to be credible. His journeys into the life are a series of temporary summer-only ventures. He is living a double life, as Kerouac himself did. Sal is a tourist, he never commits to the life and does not change. When summer is over, when the trip is at an end, Sal will return to the relative comfort of his aunt’s apartment and working on his novel. A choice real Beats don’t have the luxury of making.

It might be argued that, despite all these issues, On the Road does contain some enduring and relatable themes. I would agree that it does but they are minor, not explored in depth and are difficult to see past the obstacles of the prose style, the plot and the characters. Furthermore, the modern reader might find that other works, some of which to be fair were influenced by On the Road, have expressed these themes more endearingly and with greater strength and clarity.

For the sense of adventure, the freedom of the open road and the romance of the journey, there are probably more examples than can be listed. For the story of an inspirational, mystical or charismatic adventurer – who perhaps takes things to far – and the loyal follower he leads astray; there are again numerous examples from Fight Club to Ferris Bueller’s Day Off which can probably trace their lineage all the way back to Don Quixote. The countercultural, destruction of social convention aspects, have also been covered extensively since. On the Road feels forever tied to its period. It does not have the timelessness or cross-generational affection of, say, The Catcher in the Rye. The film Easy Rider, one of the efforts most obviously influenced by On the Road, is also deeply countercultural but probably more accessible and enjoyable. For the escapism of the road, there is always Thelma and Louise. For rejection of the drudgery of the school-work-spend-die modern lifecycle there is Trainspotting.

I read On the Road mostly during the ten days my wife was overdue with our first child. In other words, during a period where there was little else to do but read while we awaited events. I think this was the best way I could have read it. If I had to read it in my slower, more considered way, it would have been a long and painful experience. The prose style is unavoidably painful and it is perfectly understandable why so many give up on this novel within the first few pages. The plot is thin with very little to drive the reader forward. The characters are not interesting or likeable. The novel does receive much praise for its ‘innovative’ prose style and its rejection of social convention but it is hard to know how much to credit Kerouac for that. As I say, it seems more incidental than inspired. Its portrayal of an underground America and its standing as a countercultural work is more defensible. That it has been very influential is without doubt, but, as its themes have found new expression elsewhere, this does not give much for the modern reader to find in the novel other than as a cultural period piece.


  1. Enjoyed your review of “On The Road”. Have not read the book. Have watched the movie. Difficult to watch. Am curious about a few scenes of a book with the word “swan” or maybe “swans” in it. One other word in the title. Not sure of the author. Do you know what book this is and its significance in the story?

    Liked by 1 person

      • Went back and looked. The book is “Swann’s Way” by Marcel Proust. A source of inspiration, perhaps?


      • I wondered if it was ‘Swann’s Way’, there aren’t too many books I know of with ‘Swan’ in the title. Maybe an inspiration, I don’t know too much about Proust but he seems to be popular with writers who want to experiment with style and structure.


      • Hi! I’ve just finished reading the book, but haven’t watched the movie. Just wanted to say that at some point, close to the end of the book, it is said that Dean Moriarty kept Swann’s Way with him, to read between the trips. Sal notices: ‘I knew it was Dean’s high-eternity-in-the-afternoon Proust’.

        Liked by 1 person

  2. What I see in your splendid review is a young observation, of an old stereotype. As I would never defend the activities described, all I can offer you is it was a different time, place, and society. The 1940’s make the 1960-70’s look exceptionally tame. We just didn’t get the story! Ive recently gone back to re-read OTR. Im going very slow in it to try and capture the suggestions Kerouac tries hard to convey. Also OTR was the first with this kind of story to have such an effect in modern American times. The genre later became all too common.

    Liked by 1 person

  3. Thanks for the great review. I completely agree with your viewpoint. I’ve just finished reading the book and I was wondering why all the fuss about it. For most part of the reading the narrative felt pointless to me. When I thought there would be a turning point, that is, when Kerouac suggested that Sal would ‘wake up’, see the ‘real’ Dean and feel the disillusionment, the reading got a new motivation. But this turning point never really happens, not even when Dean leaves Mexico at the end of Part Four. So in my opinion the book was really a bit frustrating.

    Liked by 1 person

  4. Thanks for your review Jason. I am a little more than half the book and I am just suffering. I watched the movie this weekend to see if I am just not getting the point or to see if it is even worth it to keep reading.

    I agree with your review, but also the comment of Jeff. We are just another generation with different thinking and values. We may not understand the context of that era. It gave me the same feeling of misunderstood as the book of Madame Bovary, where the protagonist also follows her hedonistic selfish desires.

    Liked by 1 person

    • Thanks! I think it is true that being detached from that era has made it more difficult to understand. But there may still be a social detachment as well as the generational one, so even if I had lived in the same era I might not have understood them. I have been learning more about the Beats, indirectly, as a anti-materialist subculture like the Romantics and the Punks. They are all a bit socially isolated and, not being among them, I’m not sure I would ever get them.


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