"On the Road" by Jack Keruoac
A cast of dubious characters travel across the USA by road, either hitching or actually driving themselves. Starting at New York they usually end up at San Francisco by way of Denver but actually reach Mexico before the end. On their travels they are fuelled by loads of booze with a side dish of narcotics and try to jump on almost any passing female. Surprisingly they claim to be successful and on some of these occasions no cash changes hands. Sal and friends very predictably behave very badly but this is the late 40’s and compared to more recent generations its all a bit tame although I suppose it was probably considered shocking when published. I had the impression that many of the characters were rich kids posing as artists, slumming it amongst the weirdos and riff raff but all the time they know they can just send a telegram and have funds wired and so their lives and experience are fake. Reference ‘Common people’ by Pulp. But not ‘Dean’ who our narrator spends half the book trying to convince us is some kind of sainted, tortured genius and is unable to disguise that he’s actually a selfish prick who could do with a long lay down on a doctor’s couch.