Kerouac’s vagrants are literate, self-pitying, afraid of women, and condescending towards Mexicans and African-Americans. No one will confuse them with Steinbeck’s displaced Okies, and no grapes of wrath are trampled out by them. Nor are they doom-eager dreamers like Gatsby, or monomaniac questers like Ahab, or benign wanderers like Huckleberry Finn. Comparing On the Road to the masterpieces of Classic American fiction is most unkind to Kerouac.Harold Bloom
Whatever your opinion of old Harold Bloom (and my own cannot be described as favorable), that first sentence sounds about right. Kerouac's heroes belong to one of the nastiest species in the Western world's literary zoo: the dramatic young man (where "young" stands for a state of mind more than it does for a biological age - see also "man-child").
What's the dramatic young man's story in a nutshell? It is the story of easily-frustrated entitlement. The dramatic young man knows the world was supposed to be his oyster. But, alas, his life is marred by an atrocity, usually war or school, autocratic fathers, prolonged stretches of peace, dead fathers, the bourgeois, saintly mothers, literary rivals, modern art, promiscuous mothers, dead brothers, live brothers, old art, emancipated women, that sort of thing. One of these horrors, or a combination of them, has put a dent in the lovely oyster, such that our hero is loath to even touch what should have been his for the taking. He channels his self-pity into some form of rebellion against the world, which usually turns out somewhat less glamorous than he'd hoped for and ends with him either self-destructing or conforming to the rotten old world he tried to fight in the first place.
The beauty of this narrative is that it is essentially timeless, because everything in it apart from the young man at its center is a prop. To paraphrase one of the most famous passages from On the Road: "What did they call such young people in Goethe's Germany?" It almost doesn't matter when or where the story is set, the dramatic young man's drama is easy to recognize. (And for the record, I think young German hipsters at the turn of the 19th century were usually called "Oh, for Pete's sake, put that gun down, Werther was fictional!")