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On the Road features Sal Paradise, a young writer fascinated by the questionable "hero" that is Dean Moriarty. The novel involves, as you might expect, several road trips, sometimes with cars, and sometimes without. The first trip starts in New York (home base, effectively) and runs to Chicago (lots of jazz), then Denver (with Dean searching for his missing father, and hanging out with poet Carlo Marx), and to San Francisco to visit Remi Boncoeur. This trip, as all subsequent trips, features sex, drugs, alcohol, and music. Sal ends up working as a night watchman in San Francisco, only to discover that he isn’t cut out for law enforcement or for staying in one place longer than a month. He takes off again.
On the way back east, Sal meets a Mexican woman named Terry, who ran away from her husband and has a little boy. Sal figures, hey, I’m not doing anything else; I might as well live with her and almost starve to death for a month. They also pick some cotton. But then Sal thinks, you know, I’ve really had enough of this. So he heads back to New York.
Then Dean shows up with ex-wife #1, on the run from wife #2, and with Ed, who is on the run from his own wife. Dean is a little crazier than he was before, but Sal decides to go back on the road with him. This, incidentally, involves Sal leaving behind his potential wife #2. They head to New Orleans to see Old Bull Lee and his wife Jane – huge drug addicts who learn and teach and, you know, take lots of drugs. On the way they pick up lots of hitchhikers and speeding-tickets, which is by now routine.
The crew ends up in San Francisco, where Dean briefly abandons them. Crazy-orooni jazz nights ensue, and Dean can’t decide between his two women. Sal leaves for Denver, where his boredom quickly drives him back to San Francisco. There, he convinces Dean to go east and then on to Italy, because if the West didn’t bring them happiness, the only logical conclusion to go in the other direction. They stop in Denver on the way and Dean steals some cars.
The pair scores a Cadillac to drive to Chicago, and the city is wild with jazz and booze. They end up partaking in some self-destructive activities in Detroit before heading back home to New York, where Dean meets and marries wife #3. Sal leaves Dean in New York and goes to Denver, until Dean follows him there shortly after. In the novel that is Sal’s life, Dean is a recurring theme.
Dean convinces Sal to go to Mexico, where they spend lots of money, have lots of sex, and drink lots of alcohol. Then Dean abandons Sal – in Mexico – while Sal is in a dysentery-induced fever. When Sal sees him again in New York, Dean’s madness has progressed and taken on new, more silent and intense tones. Sal is unable to help his friend/hero, and reflects sadly on Dean and America, but mostly on Dean.