The world of beat was firmly entrenched in the world of bebop jazz, a music that was famously gestated during a period when its main proponents, Charlie Parker and Dizzy Gillespie, worked with Afro-Cuban musicians like Mario Bauzá and Chano Pozo. When Sal Paradise and Dean Moriarty go out in San Francisco to see jazz, they go to see Slim Gaillard, a singer and pianist who embodies the multicultural roots of bebop jazz. By some accounts born in Detroit, he was rumored to have been born in and cut sugar cane in Cuba, and invented a nonsense "jive" language that symbolically represents the confusion of Anglophones when encountering Spanish.
In the end, after disappointing all the women in their lives, Sal and Dean head for Mexico, an action that would become a rite of passage for the nascent hipster counterculture. A 1957 article in Life magazine describing the hallucinogenic powers of psilocybin mushrooms would eventually bring flocks of hippies to Oaxaca, Mexico to visit a curandera named María Sabina. Years before, William Burroughs, whose character in On the Road is called Bull Lee, played by Viggo Morgenstern, had visited the Amazon rainforest to sample the hallucinogenic plant yagé and wrote Allen Ginsberg several letters about it, eventually published as The Yage Letters.
"When they go to Mexico towards the end, I told Walter [Salles, the director] that I didn't want to write that part of the screenplay," said Rivera. "I thought they were acting like entitled, white, almost college-aged kids coming down to the Third World to sleep with 15-year-old prostitutes and get drunk and get high. And I thought, 'Wow this is where all this enlightenment leads to, just this kind of like sexual colonialism?' But Walter was very clear, he said 'You know, we really need to show them at their best and their worst, and we can't whitewash what their truth was.' And I said, 'Yes, you're right.' And that's what we did."
In the film's climactic montage/dream sequence, Sal suffers for days in a bed, feverish with dysentery. Various characters in the film flash over his head like the Tin Man and Cowardly Lion float over Dorothy when she lands back in Kansas. Bull Lee glowers at Sal, admonishing him, "You're white!"
"I liked that line, but I didn't write it," said Rivera. "It was improvised by Viggo, he came up with it…it was really intense. But it points to the limitation of the white Negro idea - isn't the whole counterculture just an outgrowth of this, forgetting the original racially charged roots of the lifestyle until they are almost entirely unrecognizable?"
Perhaps, but Kerouac - in the published novel at least - seemed to acknowledge that, in a way that some might find condescending, but others compassionate, Mexicans were free in a way he wanted to be, in a way Americans weren't.
…they knew this when we passed, ostensibly self-important moneybag Americans on a lark in their land; they knew who was the father and who was the son of antique life on earth…all Mexico was one vast Bohemian camp.