They're just good ol' boys never meaning no harm, making their way the only way they know how, but that's just a bit more than the law will allow...
The characters of Sal Paradise and Dean Moriarty in Jack Kerouac's On the Road
are 20th Century equivalents of Huck Finn and Tom Sawyer: boys having joyous American adventures. Sal and Dean trip (in more ways than one) back and forth from the east coast to the west, and down south even as far as Mexico, always looking to get their kicks. It's a free-flowing good time perfectly delivered in Kerouac's jazzy beat style.
Most of the book follows their ultimate liberation, psycho-philosophical, free-wheeling adventures bumming rides, seeing the country, scoring weed and drink, making it with real gone girls, and getting meaningless jobs along the way to further their desire to go farther, always farther. Only problem is, Sal and Dean are based on real boys. Oh sure, On the Road
is called a fiction, but it is absolutely based on real occurrences and people, so much so that Kerouac had to be dissuaded by his publisher to print their real names. Sal is Kerouac himself and Dean is his friend Neal Cassady, an essentially motherless delinquent "raised" by an alcoholic and mostly absent father. Dean/Neal, a hyper lover of life, seemed to be a manic prophet, the words and ways of which Sal/Jack was happy to follow. So when these boys steal all manner of things (including cars) or shack up and knock up women only to inevitably leave them time and again for the road, one can't help but marvel at their unconscionable irresponsibility. It smacks heavily of nothing more that having fun at the expense of others. There's only so much hedonism you can take before you have to step back and ask, what's the point?