Learn about Kerouac's personal life (see References below for biography). He wrote almost exclusively from personal experience and almost all of the characters in his books have real-life counterparts, many of whom were prominent cultural figures at the time (see Resources below for link to character key).
Read Kerouac's bibliography (see Resources below), noting the order in which his books were written. Because his writing draws so heavily from his own life, it's best to start off with an earlier work, such as "On the Road," rather than a later work like "Big Sur." His evolution as a writer and human being are apparent when his work is read more or less in order.
Download or purchase some of the voice recordings of Kerouac reading his own work. What may seem incoherent and almost impossible to read in your own head becomes clear when he reads it as it was meant to be read. It becomes much easier to understand the flow of his prose once you have heard him read it.
Find some of his earlier work. Again, "On the Road" is generally considered his masterpiece and is one of his earlier pieces. Other early work includes "The Town and the City," "The Subterraneans," "The Dharma Bums" and "Doctor Sax."
Read while listening to some Bop-era jazz softly in the background. Jazz musicians like Charlie Parker and Dizzy Gillespie heavily influenced Kerouac's writing style. Kerouac's spontaneous prose method is closely related to the improvisational jazz riffs he writes about in many of his books, and his writing has a cadence and rhythm at times that seems musical when read aloud.