The next up on my reading of the 306 greatest books is On the Road by Jack Kerouac. The book can be found on the Observer and BBC Book Lists.
As one of the seminal books of the Beat Generation, On the Road gets a sort of larger than life impression every time that I hear about it. Before I started the book I had thought it was a sort of autobiography/life lessons tale and that is sort of how it turned up after I read it. The book is essentially an autobiography, except with the names changed and, as far as I am aware, some of the circumstances adjusted for the narrative. The book essentially follows Sal Paradise in the first person role (standing in for Kerouac himself), along with the other prominent figure in the book, Dean Moriarty, standing in for his real life friend Neal Cassady. The narrative is broken up into 5 parts, each of which encompasses a unique cross country trip where Sal "just has to get away". Often times the trips are hitchhiking, bus travel, or driving a car into the dirt, and all of them are with Dean along with an assortment of other characters that come and go throughout the narrative. Taking place in the mid 1940's, post war, we are getting a different picture of America than we have today. Yes, things are cheaper, such as gas, but people are making much less and we see into the lives of those on the lower end of the socioeconomic spectrum. We live with them through the book and talk to them and really get a sense about who they are and what matters to them. That along with the prose, which is absolutely riveting, really draws you into the story. The style of the book is written based on a rambling, run-on letter that Kerouac once received from Cassady with the sentences sometimes going on and on, and other times being cut rather short. Ideas, themes, and questions are often brought up in the story and then immediately dropped, never to be answered or even acknowledged again. Kerouac's descriptions though, and his often poetic prose, makes this a beauty to read with bits and pieces of contemplative fiction and philosophy creeping in that is often profound in its take.
With all that being said, there is a major negative to the book. And that is that it's content is often homophobic, racist, misogynistic, pedophiliac, and probably lots of other negative adjectives that I can't think of at the moment. It's like these characters dive into these worlds of sex and drugs and are still able to pick out the negative stereotypes about everything. But it is weird, in that they "love" those stereotypes so it is a kind of "romanticized racism". With all of the gay characters in the book it is also super weird at how homophobic the book really is, however reading outside the book, I found out that Kerouac was rather a homophobe himself despite having almost all of his friends it seems in the LGTBQIA community. And although the book is often romanticized about it's "get out and see life" message, I see it as a tragedy, with the character of Dean slowly destroying his life through one method or another, and a character that could seriously have used medical and therapy intervention that could have perhaps helped with his constant downward spiral throughout the book. He gets to the point where he is often characterized as not being able to speak or make a sensical thought by the end of the book. If anything I see this book as a warning, and not necessarily a romantic adventure book. Overall, I would say that despite the beautiful prose, and the fantastic look at America in that time period, it is hard to recommend given all of the negatives throughout the plot and I would have to say unless you are really interested in reading it you could likely skip is and be fine.