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A certain segment of American womanhood leaned into Jack's dashing, dark, mysterious, good looks and, just under the surface, the vulnerability that stirred their protective, maternal, lustful instincts. But women were always quick to take him to their breast and feed him food for his body and his mind. Kerouac was intensely loyal to his friends no matter their peccadilloes and included them in his work in subtle guises. The associations he made while at Columbia lasted his entire 47 years. Jack got tight with William Burroughs. The same guy whose adding machine manufacturing family millions allowed him to establish new and lofty standards for world class junky-ism (hence the novel Junky) in the gutters of Mexico and Morocco while also producing Naked Lunch. Burroughs's seminal work, Naked Lunch describes a husky lesbian indeed brandishing a stainless steel dildo she nicknames "Steely Dan." Sound familiar? Allen Ginsberg had been Kerouac's best man at his wedding to June Haverty, and, along with Burroughs and Jack, formed what they called "New Vision." To give you some idea where the thinking of New Vision was, Finnegan's Wake, Joyce, was required reading. Ginsberg's notorious sexuality was no secret and some gave him heat for that. But it was Ginsberg later saying in relation to New Visions, "The new vision assumed the death of square morality and replaced that meaning with belief in creativity. I think we were quite moralistic in a way." In Dharma Bums, Ginsburg shows up as Alvah Goldbook, and was personified in On The Road as Carlo Marx. Like Joyce, Jack had a thing for puns. Years later Ginsberg would speak at Jack's memorial.  Neal Cassady was the turning of a corner. The likes of Cassady were not to be found on a campus of formal instruction like Columbia but rather the Colorado State Reformatory. Growing up in the flop houses of Denver with his alcoholic father, and losing his innocence at eight years in a gang bang, Neal became a hard core delinquent, car thief, pool hustler, and denizen of the Denver Public Library. With a virtually photographic memory stemming from an extraordinary intelligence, Cassady inhaled the library's shelves. Shakespeare, Proust, The Greeks – as much as he could get to. Hal Chase, one of the Columbia crew, met Neal during a summer spent in Colorado. He returned to New York talking about the young cowboy with the compelling blue eyes, an inner monologue he intensely spritzed, and a naturally seductive manner covering either gender. Both Ginsberg and Kerouac were intrigued, and when Cassady made it to New York with his 16 year-old first wife, they looked him up. Ginsberg was in love. He and Neal had a short fling, and Cassady became the muse for Ginsberg's early, sexually expressive poetry. Whether Cassady and Kerouac got physical is anyone's guess, but they were soul mates and almost instantly. The relationship, of course, and what they found and motivated in each other became the basis for On The Road. Jack and Neal; Sal Paradise and Dean Moriarity. According to Carolyn Cassady, one of Neal's subsequent and – having had a few marriages, some simultaneously – probably his "main wife" of 15 years, "Jack was the observer and Neal was the doer." And that of course was what Jack loved about him. They were kind of opposites that attract because Neal was very quick and nimble and Jack was clumsy and slow. So people who say they were so much alike, and looked alike, are totally wrong. They weren't at all. But they both were very compassionate and non-violent and had those sort of values I like which attracted them to each other. Then, of course, there was literature and music. Having, at one time or another, been mother and lover to both of them, no woman could have known them better. Together, Jack and Neal made their first foray into Mexico. Burroughs and his wife Joan Vollmer were already set up in Mexico City drawn by cheap drugs and an easy freedom. One of Kerouac's less recognized works, Trestessa came out of the Mexico City experience. A tale of a poor, frail, morphine addicted, street hooker, moving cheerfully resigned, through the slums of Mexico City just looking to score. The bumper car taxi cabs, the chickens and pigs strolling her rooms crowded with family and friends, fellow junkies. She would be little Terry, Sal's dalliance in Hollywood, with her great Caesarean scar in On The Road. Jack was living in Mill Valley, above San Francisco, with poet Gary Snyder (Jaffe Ryder in Dharma Bums) and he was blocked. He wrote to friend John Clellon Holmes that he didn't know what to write anymore but that he'd been playing with a long rambling poem he called automatic writing. In other words whatever ran through his mind. And, while he saw no future for it, he would finish it anyway.
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