Obviously, Sal Paradise, much like Kerouac himself, loves American jazz music, especially played on the acoustic guitar by an African-American jazz/blues giant like Huddie Ledbetter, better known as Leadbelly.
As Mark Richardson sees it, writing in "Peasant Dreams: Reading On The Road," "The strain of the basic primitive," in this case jazz, ". . . is what Sal and Dean listen to in order to hear" what they call "wailing humanity" (Texas Studies in Literature and Language, Internet) or, in other words, the vocals of someone like Leadbelly wailing out the blues, another original form of American music with roots sunk deep in the elements of jazz. For Richardson, it seems that Kerouac's application of jazz in the text of On The Road serves not only as a theme but also as the basic framework for the personalities of Sal and Dean, two rebels "on the road" and "on the beat" exploring the endless complexities of the American musical landscape.
This jazz theme in On The Road can also be applied to race and gender, for as Richardson points out, Kerouac utilizes the idea of "whiteness" as contrasted with "blackness," with the first being the so-called WASP or White Anglo-Saxon Protestant, a person who usually shuns anything to do with black culture, especially jazz music, and sees jazz musicians as peasants or those who wander from place to place, much like gypsies, without putting down social roots. As to "blackness,' this refers to African-Americans like Leadbelly, Charlie Parker and Thelonious Monk who stand in stark contrast to "White America" and find pleasure and satisfaction in playing jazz music. For Kerouac and Sal, this "whiteness" is the antithesis of jazz and is symbolized by "a suit of clothes too good to be comfortable" on the body of a jazz-loving, "on the beat" rebel more suited to non-conformity ("Peasant Dreams," Internet).
Richardson also makes reference to the...
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