This is the book which has given me anxiety attacks on sleepless nights.
This is the book which has glared at me from its high pedestal of classical importance in an effort to browbeat me into finally finishing it. 
And this is that book which has shamed me into feigning an air of ignorance every time I browsed any of the countless 1001-books-to-read-before-you-die lists.

Yes Jack Kerouac, you have tormented me for the past 3 years and every day I couldn't summon the strength to open another page of 'On the Road' and subject my brain to the all-too-familiar torture of Sal's sleep-inducing, infuriatingly monotonous narration. 

Finally, I conquer you after nearly 3 years of dithering. I am the victorious one in the battle in which you have relentlessly assaulted my finer senses with your crassness and dared me to plod on. I can finally beat my chest in triumph (ugh pardon the Tarzan-ish metaphor but a 1-star review deserves no better) and announce to the world that I have finished reading 'On the Road'. Oh what an achievement! And what a monumental waste of my time.

Dear Beat Generation classic, I can finally state without any fear of being called out on my ignorance that I absolutely hated reading you. Every moment of it. 

Alternatively, this book can be named White Heterosexual Man's Misadventures and Chauvinistic Musings. And even that makes it sound much more interesting and less offensive than it actually is. 

In terms of geographical sweep, the narrative covers nearly the whole of America in the 50s weaving its way in and out of Los Angeles and New York and San Francisco and many other major American cities. Through the eyes of Salvatore 'Sal' Paradise, a professional bum, we are given an extended peek into the lives of a band of merry have-nots, their hapless trysts with women, booze, drugs, homelessness, destitution, jazz as they hitchhike and motor their way through the heart of America. 
Sounds fascinating right? (Ayn Rand will vehemently disagree though). 

But no, it's anything but that. Instead this one just shoves Jack Kerouac's internalized white superiority, sexism and homophobia right in the reader's face in the form of some truly bad writing. This book might as well come with a caption warning any potential reader who isn't White or male or straight. I understand that this was written way before it became politically incorrect to portray women in such a poor light or wistfully contemplate living a "Negro's life" in the antebellum South. But there's an obvious limit to the amount of his vile ruminations I can tolerate.

"There was an old Negro couple in the field with us. They picked cotton with the same God-blessed patience their grandfathers had practiced in ante-bellum Alabama."

Seriously? God-blessed patience? 

Every female character in this one is a vague silhouette or a caricature of a proper human being. Marylou, Camille, Terry, Galatea are all frighteningly one-dimensional - they never come alive for the reader through Sal's myopic vision. They are merely there as inanimate props reduced to the status of languishing in the background and occasionally allowed to be in the limelight when the men begin referring to them as if they were objects.
Either they are 'whores' for being as sexually liberated as the men are or they are screaming wives who throw their husbands out of the house for being jobless, cheating drunks or they are opportunistic and evil simply because they do not find Sal or Dean or Remy or Ed or any of the men in their lives to be deserving of their trust and respect, which they truly aren't.

And sometimes, they are only worthy of only a one or two-line description like the following:-

"...I had been attending school and romancing around with a girl called Lucille, a beautiful Italian honey-haired darling that I actually wanted to marry"

Look at Sal talking about a woman as if she were a breed of cat he wanted to rescue from the animal shelter. 

"Finally he came out with it: he wanted me to work Marylou."

Is Marylou a wrench or a machine of some kind? 

And this is not to mention the countless instances of 'get you a girl', 'get girls', 'Let's get a girl' and other minor variations of the same strewn throughout the length of the book and some of Sal's thoughts about 'queers' which are equally revolting. 

Maybe I am too much of a non-American with no ties to a real person who sees the Beat era through the lenses of pure nostalgia or maybe I am simply incapable of appreciating the themes of youthful wanderlust and living life with a perverse aimlessness or maybe it's the flat writing and appalling representation of women. Whatever the real reason(s) maybe, I can state with conviction that this is the only American classic which I tried to the best of my abilities to appreciate but failed.