Jack Kerouac (1922–1969)

This is one of the saddest books I've ever read. Years ago, I read the first volume, taking us up to 1956. He came across in that book as enthusiastic, motivated to be a great writer, and a good friend. That all changed when 'On the Road' was published, which is when this volume essentially begins. It brought him fame and notoriety but wasn't a financial success. It was the beginning of an eleven year slide into alcoholism (among other vices) and bitterness. Through it all, though, he kept show more up a spirited correspondence with his agent, Sterling Lord - who I believe only passed away in the last couple of years. And he was quite prolific to his sad end in his output of 'Duluoz Legend' novels. Despite the gloom, still an interesting read. show less

Everyone tells you On the Road is about freedom. About breaking free from the suffocating conformity of 1950s America, about finding yourself on the open highway, about the ecstatic possibility of movement and experience. Jack Kerouac typed it in three weeks on a continuous scroll of paper in 1951, fueled by benzedrine and jazz rhythms, and when it was finally published in 1957, it became the bible of the Beat Generation.

People still clutch it like a sacred text, still talk about how it show more changed their lives, still plan cross-country trips because Dean Moriarty made reckless driving look like spiritual enlightenment. But read it now, actually read it, and something else emerges: a chronicle of emotional vampirism disguised as adventure, a celebration of selfishness mistaken for liberation, and a narrator so enchanted by his own immaturity that he mistakes chaos for profundity.

Sal Paradise worships Dean Moriarty from the first page, and that worship blinds him to what Dean actually is, a con artist with good cheekbones and the ability to talk fast enough that people don't notice he's stealing from them. Dean abandons pregnant wives, ditches friends when they're sick, steals cars, bounces checks, leaves destruction in his wake, and Sal treats all of it like performance art.

The novel wants you to see Dean as a holy fool, a madman-saint who's too pure for conventional morality. But strip away Sal's breathless narration and what you're looking at is a narcissist who uses people until they're empty and then moves on to the next source of food and money and admiration. The freedom everyone celebrates is just the freedom of someone who refuses to be responsible for anything, including the human wreckage he creates.

The women in this novel don't exist as people. They're ports of call, bodies to sleep with, sources of money or shelter or maternal comfort. Sal and Dean blow through girlfriends and wives like they're going through tanks of gas.
When Dean abandons his second wife Camille, who's just given birth to his child to go joyriding with Sal, Kerouac writes it like a scene of liberation. The baby crying in the background is just ambient noise, not a human being Dean's abandoning. Marylou gets passed between the men like shared property. The Mexican prostitutes are exotic scenery.

Every woman exists only in relation to what she can provide the men, and the moment she wants something back: commitment, honesty, basic decency, she becomes a drag on the adventure, a reminder of obligations that must be escaped.

The prose style gets praised as spontaneous and jazz-like, but spontaneity isn't the same as good writing. Kerouac's run-on sentences pile up observations without discrimination, everything matters equally, which means nothing actually matters. He describes crossing Nebraska with the same breathless intensity he describes having intimacy or listening to bebop or eating apple pie.

The lack of editing isn't authentic, it's lazy. It's a writer refusing to make choices about what's important, hiding behind the claim that the unfiltered consciousness is more real than crafted art. The result reads like someone who won't shut up at a party, who thinks every thought that passes through their head is worth sharing at length.

If you read against Sal's adoration, the book reveals how boring and repetitive this lifestyle is. They drive across the country. They run out of money. Someone's aunt or girlfriend wires them cash. They drive back. They get jobs they quit within weeks. They talk about everything being "IT" the ineffable experience that jazz and speed and movement are supposedly reaching toward, but they never define what IT is because IT is nothing.

It's the emptiness at the center of all this motion. Dean keeps moving because stopping would mean facing what he is, and what he is turns out to be a hollow man who's convinced himself and everyone around him that the hollowness is actually enlightenment.

The racial politics are even worse than the gender politics. Sal and Dean fetishize Black culture: jazz musicians, poverty, what they imagine as authentic suffering. They want to be Black because they think Black Americans have access to some raw, real experience that suburban white kids lack.

"I wished I were a Negro," Sal says at one point, in one of the novel's most cringe-inducing passages. He wants the culture without the oppression, the music without the systematic racism that created it. The entire Beat fascination with "primitivism" is just colonialism in bohemian clothing, white guys slumming it in Black neighborhoods, treating real people's lives as material for their spiritual tourism, then going back to being white whenever it's convenient.

The book's treated as a rebellion against conformity, but what's it actually rebelling toward? Dean and Sal aren't building anything, aren't fighting for anything, aren't creating any alternative to the suburban nightmare they're fleeing. They're just consuming: experiences, people, places, drugs, intimacy, without producing anything except more need for the next consumption. It's not a revolution. It's arrested development. These are men in their late twenties acting like teenagers and calling it enlightenment because they've read some Spengler and can name-drop Proust while stealing cars.

The ending tries for tragedy. Dean, aging and broken, abandoned by everyone he abandoned first, showing up sick and needing help, and Sal finally seeing him clearly. Except Sal still doesn't quite see it. He's still romanticizing, still finding profundity in Dean's degradation.

The novel can't fully commit to recognizing that this whole glorious adventure was actually just waste, wasted time, wasted relationships, wasted potential. Kerouac keeps trying to find meaning in meaninglessness, to make the refusal to grow up look like spiritual seeking.

Here's what On the Road actually offers: permission. Permission to be selfish and call it freedom. Permission to hurt people and call it honesty. Permission to refuse responsibility and call it rebellion. Permission to treat life like a resource to be extracted rather than something to be built or shared or given to.

For young people, particularly young men, who feel trapped by expectations, who want to believe they're special enough that normal rules don't apply, this is intoxicating. It tells them their self-absorption is actually self-discovery, their cruelty is actually courage.

The tragedy is that there's a real critique buried in here somewhere. 1950s conformity was suffocating. Suburban life was often soul-deadening. The pressure to marry young and get a company job and buy a house and never question anything was genuinely oppressive. But Kerouac's answer: reject all of it, keep moving, refuse to commit to anything or anyone, isn't liberation. It's just the opposite trap. You can waste your life in a gray flannel suit or you can waste it driving in circles across America, but either way you end up at the same destination: old, alone, and wondering what it was all for.

On the Road celebrates the second kind of waste and calls it freedom, and generations of readers have believed the marketing. But scratch the surface of all that ecstatic movement and what you find isn't enlightenment. It's just someone running from themselves and calling it a journey. (anonymous FB post) show less

This is a worn down and haggard Jack, fighting to keep some of that idealism and spark alive, but well aware that he can't outrun fame, addiction, or myriad other demons eating away at his body and spirit.

For joyous, crackling prose, I prefer "Dharma Bums", but for a character study of what happens when a guy who delights in the simple joys gets caught up in the heat and confusion of being deigned king of an entire cultural movement, "Big Sur" is mighty compelling.

The only other Kerouac I've read is On the Road, which I liked a lot. This one is a quick sketch of Kerouac's crowd of cool kids in San Francisco, and a love affair gone bad due to the narrator being kind of an asshole (as are most of the cool kids). But at least he's an asshole with some insight about himself and others, and a good eye and ear, so there's a lot of dense, vivid description of places and people. There's not a whole lot else: in between boy-meets-girl and boy-chases-girl-away show more they mostly hang out with the gang in various places, and some aimless unruliness happens; you could put those scenes in any order. On the Road has a very loose shape but it is a shape - the places he goes are distinct, and we see Moriarty go through different stages of distress - whereas this book, despite the charged-up free-associating prose, is pretty static. Whenever it gets back to Mardou (the girlfriend) and the narrator's belated attempts to imagine what's going on in her mind, it comes to life and makes you love them both, sad and frustrating as that is. show less