Wired's copy chief, Tony Long, makes the case that On the Road belongs in the "geek's literary canon":
Whether Kerouac was a "great" writer is certainly debatable (define "great," for starters); that he was one of America's most influential writers is beyond dispute. On the Road, at 50, sells more copies in a given year than most new fiction does, so it evidently still strikes a chord somewhere.
Kerouac gets kicked around pretty good in academia and by other writers, mostly East Coast snoots who wrinkle their noses at the idea of automatic writing. It was Truman Capote, remember, who dismissed Kerouac with one of the bitchiest literary putdowns of all time: "That's not writing, that's typing."
Without a doubt, writing on a scroll in a nonstop, three-week frenzy of Benzedrine-fueled inspiration doesn't represent the height of literary craft. But On the Road is a banshee cry for freedom, not pop literature, so in this case Kerouac's improvisation thoroughly guts Capote's measured prose.
While you're digesting that morsel, try this one: On the Road is as deserving of a place in the geek's literary canon as anything penned by Tolkien, Gibson or Dick. Kerouac didn't invent alien civilizations or futuristic worlds, but he helped break down the walls of convention in the real one. If the modern geek is the maverick he often claims to be, then he owes at least a cursory nod backward to a genuine maverick, one who helped pave the way while on a hopeless struggle to find himself.
Fifty years along, On the Road still resonates for those of us possessed of a restless spirit, who see gray conformity as spiritual death, who place the value of the individual above the mere possession of things. For us, Sal Paradise's odyssey stands as the antidote -- and as a warning to keep a close watch on our souls.