From troubled youth to literary legend

Hidden in an otherwise joking, high-on-pot, mocking letter to Allen Ginsberg in 1947, Neal Cassady offhandedly gives the key to his life: “[S]ee how I write on several confused levels at once, so do I think, so do I live, so what, so let me act out my part at the same time I’m straightening it out, so as to reach an authentic destiny.”

Millions of people around the world have heard of this man, born in 1926 and raised by a derelict, alcoholic father on Denver’s Skid Row during the Depression, and many think they knew who he was: the fast-talking, womanizing sidekick of Jack Kerouac and hero of Kerouac’s most famous novel, “On the Road”; the “secret hero” to whom Ginsberg dedicated his first book, “Howl”; the primary archetype of the hot (as opposed to cool) hipster; the driver of Ken Kesey’s psychedelic bus and star of the Merry Pranksters; the first and most notorious martyr to America’s paranoid anti-marijuana laws, and many other seminal roles.

But as “Neal Cassady: Collected Letters, 1944-1967” shows, he was far more. To begin with, he was an exceptionally gifted thinker and writer, almost wholly self-taught; he was a pioneer theorist on fiction writing whose enormous energy helped to push fiction into the twin eras of postmodernism and new journalism; and he called himself the most “balled-up” man on the planet.

Abandoned by his mother at 6, Cassady grew up mostly on the streets with little adult supervision; predictably, he got into trouble early and often. It wasn’t long before he went from boosting change off newsstands to stealing cars for joy rides with girls. At 12, he had sexual intercourse for the first time, igniting a ferocious appetite for women that would consume him. Though never his great passion, he also began having sex regularly with men and soon discovered that he could make a passable income as a male hustler. A great part of Cassady’s charm was physical: his ruggedly handsome face with its startling blue eyes and what Kerouac called his Franklin D. Roosevelt chin, and an incredibly manly body -- wide shoulders, big biceps, narrow waist, powerfully muscled legs. Like Kerouac, he was a natural athlete; unlike Kerouac, he was not shy with women or men.

What saved Cassady from disappearing into a life of “iron sorrows” -- Kerouac’s name for Cassady’s propensity for prison life -- was a chance meeting at 15 with Justin Brierly, a wealthy, cultivated Denver lawyer who was gay and -- in an era and place where homosexual behavior was not condoned -- developed relationships with numerous young men whom he coached and recommended for admission to his alma mater, Columbia University. Besides falling in love with Cassady, Brierly recognized the teenager’s exceptional mind and drive to succeed and immediately offered Cassady his considerable educational and social influence. And Cassady, who had learned confidence games to survive long before his voice changed, made use of Brierly’s fascination.

Still, the teenager could not keep out of jail. Cassady began taking stolen cars farther and eventually was arrested in Los Angeles in 1943 and sent to a youth camp for six months. He soon escaped and returned to Denver; more arrests followed. In 1944, he was sentenced to a year in the Colorado State Reformatory at Buena Vista. “The Collected Letters” opens with Cassady’s Oct. 8, 1944, letter to Brierly from that reformatory. He is clearly trying to impress the older man, but the letter reveals his enthusiasm for books and the precise, minute-to-minute schedule he set for himself -- what would become a lifetime habit of using his time to its maximum. In later letters to Brierly, Cassady sketches a reading list that would do credit to an East Coast preppy: Philip Wylie, the Harvard Classics, Dickens, Twain, Thomas Wolfe, Freud, Socrates and Santayana. Though he doesn’t mention it, he also was devouring Dostoevski, including “The Idiot,” which would later put him in good stead with Kerouac and other Beat compadres.

Out of the reformatory at 19 and filled with plans to go to New York and enter Columbia, Neal’s life began to tumble rapidly in many directions. At Pedersen’s Pool Hall in Denver he met his lifelong friends Al Hinkle, Bill Tomson and Jimmy Holmes. Their youthful high jinks would give way to jobs and marriages; Cassady’s wildness escalated. He stole some 500 cars; seduced women all over town, including a daughter, mother and grandmother who lived in the same house; got more than a few women pregnant; and was constantly on the run from police. (He returned to prison at 32 when he was sentenced to two years in San Quentin for giving away two joints to an undercover narc in 1958.)

At 20, after marrying a 16-year-old beauty named Luanne Henderson, Cassady stole her uncle’s car and drove at top speed for New York. The car didn’t make it, but Neal and Luanne did, stepping off the Greyhound bus into Times Square in December 1946, Proust and Shakespeare in his suitcase and hardly enough money for one automat meal in his pocket. Another Brierly protege, Hal Chase, took them to the West End Bar to meet some of his Columbia University friends, including Ginsberg and Kerouac. Ginsberg fell in love with Cassady; Kerouac was in awe of him. Cassady latched on to both men, not only as possible tickets to the cultivated, literary life he’d always imagined for himself, but also as the loving brothers he’d never had. The rest, as they say, is history.

The three of them would chase each other across the continent endlessly -- to Denver, San Francisco, Texas, Mexico City, Chicago and back to New York -- creating material for countless novels, stories and poems and, as this book of letters shows, amazingly conscious that this was what they were doing. Reading letters Cassady wrote to Ginsberg and Kerouac less than a year later -- in the fall of 1947 -- after he’d run off to San Francisco with yet another new love, Carolyn Robinson, it is hard to believe that he was only 21 and had been what Kerouac called a “jail kid” just a few years earlier. Among other things, Cassady writes of hearing author Thomas Mann discuss Nietzsche’s superman -- a “problem,” he notes, they all were wrestling with -- and the triteness of Lord Chesterfield’s 18th century ideas of mature development. In almost the same breath he refers to getting high on some “good tea” (marijuana), the “rococo” textures of Dexter Gordon’s saxophone and the “kick” of conning a junkie named Stephanie.

Cassady’s philosophy of life, enunciated throughout these letters, was simple -- and seductive. “That the will is all, has, and always will be my basic concept,” he writes Kerouac in April 1947. His basic temperament, he explains, combines an attitude of “not to worry about worry” and a “native enthusiasm.” Growing up among the destitute, he writes that he learned early that life offered no guarantees and so he habitually “anticipate[d] none.” Instead, he could use his own will and intelligence to extract some benefit. His core belief was not so different from Saroyan’s exhortation, “In the time of your life, live,” or Henry James’ “Live all you can.” Cassady’s mantra was even simpler: “I have yet faith.” Kerouac would echo this over and over, but especially in “On the Road,” in which the Cassady character, Dean Moriarty, speaks some of the book’s most famous lines, such as, “We know TIME and we know that everything is really FINE.”

In an Aug. 10, 1948, letter to his Denver friend Tomson, Cassady says the trick is “to see you are nothing, then grow into something” and brags that he has “used women, tea and psychology” to turn his life around. The question this collection keeps thrusting at us, but unfortunately does not answer, is whether Cassady grew into a great man or a monster.

On the side of greatness is the indisputable fact that Kerouac would not have become the revolutionary novelist we know or made enormous breakthroughs in modern fiction without Cassady’s literary insights and textual examples. When they met, Kerouac was working on his first novel, “The Town and the City,” a Wolfean family saga with a lot of ornate description of people and places but virtually no originality. Almost immediately, Cassady bombarded Kerouac with demands that he write directly from life, in the rawest language possible, the kind used in talking to a friend:

“I have always held that when one writes one should forget all rules, literary styles, and other such pretensions as large words, lordly clauses and other phrases as such, i.e., rolling the words around in the mouth as one would wine and proper or not putting them down because they sound so good. Rather, I think, one should write, as nearly as possible, as if he were the first person on earth and was humbly and sincerely putting on paper that which he saw and experienced, loved and lost; what his passing thoughts were and his sorrows and desires; and these things should be said with careful avoidance of common phrases, trite usage of hackneyed words and the like.... Art is good when it springs from necessity.”

Cassady prefigures many of the specific breakthroughs for which Kerouac is renowned, including sound and voice experiments with a tape recorder and transforming the theory behind action painting into spontaneous prose. In one evocative passage, he describes to Kerouac how the full experience of art must involve one’s whole body: “Breath comes quickly, eyes close in squinty anticipation, head lowers until chin point is almost vertical, feet spread as heels raise slightly, hands seek nearest object with fingers quiveringly, tantalizingly caressingly poised, belly tightens, from each buttock twin masses of balled nerves join at base of expectant spine.... “

Kerouac is frequently credited with having written the first postmodern novel in “Visions of Cody,” his second book ostensibly about Cassady but one that questions whether there is any reality whatsoever -- let alone an actual person -- that can be known and written about. One surprise in this collection is to find that the idea came from Cassady: “Not in any sense of ‘truth’ am I writing,” he tells his second wife, Carolyn. “[T]here is none actually that can be recognized, & ‘truth’ is a matter of the understanding process only ... & since each of us can not really understand each other -- in the sense that time defeats ability to understand anew & afresh each instant.... “

Unhappily for all involved with Cassady -- and for the reader who must slog through a tortured soul’s descent into darkness and self-destruction -- this book does not stay long in the realms of literary theory but increasingly reflects an utterly selfish and, at times, thoroughly unlovable individual. With the best of intentions and an apparently sincere desire to see everyone be happy, Cassady would promise anything then, rather than try to keep these promises, spend his energy devising elaborate explanations for his failures. In many ways he fit the classic profile of a sociopath, and his brilliance and good looks gave him a bigger edge in taking advantage of everyone around him. Cassady’s insistence that he lacked emotion, his inability to focus on productive work such as an autobiography he never finished and what he called his growing “blankness” all point to a serious pathology.

A recently discovered cache of letters from Cassady to his third wife, Diana Hansen, whom he impregnated, married, then divorced to remarry Carolyn, is perhaps the most revealing in the collection, but editor Dave Moore apparently made little effort to find other letters besides Cassady’s already-known and voluminous correspondence with Kerouac and Ginsberg. Letters from others are thrown in sporadically with no real sense of purpose. There are far too many letters from Carolyn Cassady to her husband, often detailing nothing more important than her procedures for bathing the children. Perhaps most disappointing, there are only a smattering of letters from 1954 on -- the crucial last 14 years of Cassady’s life.

It seems probable that Carolyn Cassady, with whom Moore worked closely, had a large hand in determining which letters were included and which subjects were broached. There are a maddening number of prefaces that digest what is in the letters and an equally maddening number of useless footnotes, telling us who Dr. Benjamin Spock and Dante are, for example, yet none commenting on the many mysteries Cassady alludes to -- such as the alleged existence of numerous illegitimate children, his apparent preference for violent sex or his claim that he had “no feeling for females except sexual ones.”

Despite these flaws, “Collected Letters,” by putting together such an array of Cassady’s thoughts in one volume, creates a watershed in our understanding of Neal Cassady’s genius, as well as illuminating the price a lot of people had to pay for it. *