TL;DR: On the Road is the 1950s version of Eat, Pray, Love (with more sexism) and you can't change my mind.

This book does not deserve all the praise for being the voice of an American generation. There were some redeeming qualities, most notably how Kerouac captures the spirit of America and creates this idea of the “all-American road trip.”

However, On the Road’s flaws frequently tend to outshine its gems. While at times gorgeous, Kerouac tends to ramble and his style becomes almost Dickensian at times. Evoking the wisdom of Michael Scott, Kerouac likes to start sentences without knowing where they’re going and just hopes he finds them along the way. There were several times where I was forced to skim pages because he would talk about a minor character and all of the details of their personal life (which had no impact on the story) for two whole pages.

On the Road’s biggest shortcoming is that, to put it bluntly, it is a largely autobiographical account written by a straight white financially privileged male. In some cases, this is not the worst thing, but for a coming-of-age novel dealing with themes such as freedom, this vantage point makes the book a nuisance to read. For starters, Sal Paradise, Kerouac’s alter ego, is not a likeable protagonist. A Columbia University dropout who lives with and is financially supported by his aunt, he lacks a personality of his own as he frequently associates with and yearns to be with people he deems more exciting than himself. His attempts at “finding himself” through driving cross country appear very privileged, especially when he can wire his aunt at any time when he is running low on money. Sal’s road trips are essentially the 1950s version of Eat, Pray, Love by Elizabeth Gilbert.

Sal’s foil is the potentially even less likeable Dean Moriarty, an often shirtless and lawless man-child who is almost never held accountable for his actions. While Dean’s spiritual revelations and passion for life make him a far more interesting character than Sal, his treatment of women is grotesque. While both Sal and Dean highly objectify women and treat them as nothing more than commodities, Dean’s character is much more involved, as he holds relationships with three different women during the course of the book, while at the same time expressing admiration for women much younger than himself. The double standards than Dean has for women are, to put it lightly, absolutely insane. He expects his three lovers, Marylou, Camille, and Inez, to all be loyal to him as he drives around the country and has sex with other women. In addition, he impregnates Camille and Inez (Camille twice) and then immediately runs off and provides no support for his children. Dean’s double standards are fully displayed when he gets into a fight with Marylou in San Francisco. Out of all of Dean’s wives, Marylou is the only one who will not put up with Dean’s cheating habits. Once Marylou expresses this, along with the fact that she has been sleeping with other men, Dean hits her and permanently disfigures his thumb. Despite his frequent sexual misconduct, On the Road treats Dean as the story’s hero, the consequences for his actions only extending to receiving the light-hearted nickname “The Holy Goof.”

This book is written by a straight white man for straight white men, and I'm still baffled as to why it's considered a classic.