On the Road
Jack Kerouac
1951-1957
For years I had a vague feeling that I should read this, but really didn’t want to, because people I knew in college wrote so much terrible crap under his influence—and maybe because I associated it with macho cool, and thought it might make me feel wimpy and naive. Fortunately I got over it and this really is a great novel.
Kerouac and his friend Neal Cassady (a.k.a. Sal and Dean) travel around, lose each other off and on, settle down once in a while, meet people. Dean is a broken person, kind of sociopathic in a non-aggressive way, but he’s entertaining so he gets away with things; Sal is obsessed with trying to figure him out and describes him as a mythic figure, and Sal has some big ideas about himself too: writer, free spirit, representative of the new jazz bohemia, etc. But somehow even so, the book doesn’t really allow him or Dean to become larger than life; things keep happening around them and in spite of them, and Sal keeps losing sight of his navel and getting caught up in the stories of others. Kerouac describes a diverse assortment of people, landscapes, towns, jobs, and relationships, all with such affection that you can see why Sal wants to keep moving and see them all, but he (mostly) manages to avoid the sense that they’re all just about what they mean to the narrator—he values them for just existing, and Sal also understands at some level that Dean is whatever he is and has his own story.
It would be stupid to use this as a template for your own pursuit of happiness, and many of the characters behave very badly, but it’s a very humane book. The prose has a casual elegance and it’s also pretty funny. Read it for what’s in it, not for the mythology.
The Subterraneans
Jack Kerouac
1958
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 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, as sad and frustrating as that is.