Blog: Kerouac’s Winding Road

Halfway through reading Jack Kerouac’s On The Road I wondered if I had made a mistake. For a book that revolutionized American literature, it had a hard time keeping me interested. The opening chapters of the book drew me in with their analysis of human actions and c’est la vie mentality, but the repetition soon got to me.

Nevertheless, I trudged on through the remaining hundred or so pages until I had made it to the end and there, amazingly, I was brought to tears.

I wanted to immediately start the whole book over again and follow the ever-discontented Sal Paradise and his mercurial friend Dean Moriarty across the country again and again.

Written on a single roll of typing paper, Kerouac’s On The Road describes his experiences traveling the country with his friends during his college years at Columbia University, with some liberties taken of course. His name and those of his friends have been changed and, being fiction, episodes and adventures are much more dramatic than those that occurred in Kerouac’s life.

The story follows a young Sal Paradise as he is roped in by his friend Dean to go on a cross-country, hitch-hiking adventure. Along the way they converse with hobos, fall in love time and time again, and meet with great minds of the “beat generation.” Though this initial concept is entertaining, it slowly loses its novelty as the same trip occurs two more times as Sal moves back and forth across the country.

So why is it worth reading past the first section? Kerouac performs the herculean task of capturing humanity, both the painful and the humorous sides. He works as a sharecropper, hitches a ride with out of work hipsters and watches as his friends either settle down or spiral into self destruction.

As a member of the male portion of the population, I connected especially well with the line, “A pain stabbed my heart as it did every time I saw a girl I loved who was going the opposite direction in this too-big world.”

Although you want to cry out as the characters make bad decision after bad decision, whether it be with drugs or relationships, you cannot help but feel that maybe, just maybe, life might be better with the freedom that comes from being on the road.