I am a late-comer to On the Road by Jack Kerouac. It is the kind of book that people read in their late teens/early twenties as a classic road trip book that should offer enlightenment as to the meaning of life, as a catalyst to leading a more fulfilled and meaningful existence. I need to admit, had I read this book during that time of my life, I am pretty certain I would not have understood or appreciated it.
Having now read the book, I feel that to fully understand it and to appreciate the impact it made when published, it shouldn’t be read in isolation. It is one of those rare books that requires a bit of extra reading around the edges. You need to be prepared to do some research and background checking to get a feel for the historical context and the intellectual movement that Jack Kerouac and his contemporaries started.
Some time ago during a visit to San Francisco that included a road trip down Big Sur, highway 1, I became familiar with the term “Beat”. I had heard it before, but never knew really what it meant. The guidebooks were full of references to Beat Poets and the Beat Generation. Jack Kerouac was the first in his group of intellectual friends to coin the phrase Beat Generation, incorporating themes such as being downtrodden, dead tired, beatific (in the religious sense of euphoria), or the beat of music especially improvised jazz. It was a term intended to capture the feelings of a post-depression, post-war generation who felt disenfranchised and restless to find more meaning in life than the conformity and social acceptability of middle-class America. The group was mainly made up of intellectuals; poets, writers and philosophers who congregated around Columbia University.
On the Road is a semi autobiographical story based on events that took place during the late 40s. It chronicles the travels and adventures of Sal Paradise, a young writer (based on Jack Kerouac) and his friend Dean Moriarty (based on Jack’s friend Neal Cassidy). Sal and Dean meet through a mutual friend when Dean decides he wants to learn to become a writer. Sal soon falls under Dean’s charms and is intrigued by his craziness. He calls Dean “the holy con-man” which describes Dean’s character pretty accurately as he can rarely do wrong in Sal’s eyes and yet plays the trickster, serial womaniser and all round live-wire. Sal realises early on that at some point Dean will let him down and disappoint him. There is a real poignancy to this realisation. I didn’t like Dean as a character. He is unreliable, rude and behaves abysmally towards the women in his life and some of his male friends. However, I felt incredible sympathy for him. We hear about his background; Dean is constantly looking for his drunk father who was in and out of prison and abandoned him early on; We hear of a cousin who issues Dean with paperwork formally cutting ties with his extended family; We meet a childhood friend who looks at Dean with distrust and doesn’t want him to come back and visit again. It’s all very sad and goes some way to explain his behaviour. His whole life Dean was disappointed and let down by everyone around and yet Sal knows that eventually Dean will copy this behaviour.
When Dean travels back west after his visit to New York, Sal promises to visit him later in the year. The first part of the book follows Sal on his solo journey across America and back again. He hitchhikes west, meeting vagrants and travellers en-route. He meets up with his old friends and Dean in Denver before heading on the San Francisco, Bakersfield and, once Autumn draws in, back home to New York. The rest of the book follows Sal and Dean on 3 further trips back and forth across America and south into Mexico. On each journey they tell stories and discuss life, they are look for “it”, but never really know what “it” is, they just know that the road is straightforward, pure, uncomplicated and allows them to live in the present. It seems that only when they are on the road can they put their disappointments behind them. When commenting on some of the car-share kids travelling with them on one leg of a journey, Dean hits on the crux of their philosophy. He rages about how they worry about their bourgeois, materialistic lives, they worry about things they have no influence over. To him these worries are not just a waste of time, they are a betrayal of time.
Throughout their travels there are episodes where they meet up with old friends, visit jazz clubs, go to parties and each outing serves as a reminder of their chaotic, frenetic lives and the lives of their friends and contemporaries. As Sal and Dean are based on real people, so are some of the other characters in the book. The poet Allan Ginsberg makes an appearance as Carlo Marx and William Boroughs becomes Old Bull Lee.
On the Road is a book driven by its characters, so if you prefer plot driven stories, this may not be for you. The first person narrative can also be somewhat off-putting as huge passages become a stream of consciousness unfolding of thoughts rather than structured paragraphs. I didn’t love this book, but I do think it is a remarkable book in terms of its themes and principles. I had to keep reminding myself that this was not a book written in the 60’s when hedonism and frivolity were commonplace. I couldn’t think of its British equivalent – I think in those post-war years we were too shell-shocked to have produced something as progressive (but please prove me wrong!). I’m very glad I’ve finally read it and feel more rewarded two weeks after finishing it and having let it sink in.
A Fiction Habit 
I’ve been meaning to read this and will definitely take your advice and be prepared to do some extra research!
I came across this interview in The Paris Review with Kerouac. You might already have read it but I thought I’d send it to you.
http://www.theparisreview.org/interviews/4260/the-art-of-fiction-no-41-jack-kerouac
I like your idea of finding out more about the history and the culture of the society in which a book was written. The books I’m reading from Bennett’s list are separated from us from anything from sixty to over a thousand years. My dad and I had a recurring discussion about whether you needed to know anything about the author to understand better their work. I do think having a better idea of the world in which the book was read can challenge some of the myths that rise up about a book. As you write, On the Road was written before the hedonism of the sixties. The forties and fifties was a much more buttoned-down era of social values and culture in general.