Neal Cassady and the Basics of Beat

Booknotes looks at the writer who spurred Kerouac to write "On the Road"

Neal Cassady (left) and Jack Kerouac

Mike Selby

“I first met Dean not long after my wife and I split up. I had just gotten over a serious illness that I won’t bother to talk about, except that it had something to do with the miserably weary split-up and my feeling that everything was dead.” These are the opening words to one of the most celebrated books of all time—Jack Kerouac’s “On the Road.” Kerouac was part of the Beat Generation, a phrase he actually coined himself. He felt he and his friends were beat by society’s post-war expectations; they were weary, raw, and felt used. The original Beats were nothing more than a small group of friends lead by Allen Ginsberg, which—besides Kerouac—included Lucien Carr and William Burroughs. After Carr was sent to prison for murdering a predatory stalker, this group found themselves further united in an avant-garde way of producing literature.

Then in the winter of 1946, along came Neal Cassady, and everything changed.

Born in 1926, Cassady was raised in poverty and physical abuse by an alcoholic father; he never finished high school. The universe seemed to counter these circumstances by giving Cassady stunning looks (think a young Paul Newman) and an IQ of 120. By the time he met Kerouac and company, he had stolen close to 500 cars—the same number of his sexual conquests. While some felt he was nothing more than a con-man lacking a conscience, he never conned anyone out of anything more than a free beer.

Fascinated by Cassady’s incredible charm, Kerouac joined him on a road trip all over the United States. He soon found himself somewhat dazed by his new friend’s lack of inhibitions, sense of adventure, chronic womanizing, and dearth of responsibilities. Even though Kerouac would occasionally find himself abandon in some strange city, he remained extremely fond of his friend.

So much so that he wanted to write about their trip. He tried for a year or two, but what he wrote never captured the frenetic energy of the real-world Cassady. Then in December of 1951, Kerouac received a letter from Cassady, now known as the “Great Sex Letter.” In it, Cassady describes how he tried to have sex with a woman on a bus, and when that failed, was successful with another woman sitting beside her. It wasn’t the content of the letter which moved Kerouac (he had already received one describing an equally detailed mother / daughter tryst), but the style of writing. Somehow Cassady was able to write exactly as he spoke, with his unusual restrained and wild manner coming across in each sentence.

By applying this technique to his own writing, Kerouac banged out “On the Road” in a record three weeks. In it, Kerouac not only expertly captured Cassady’s essence with the character of Dean Moriarty—”the sideburned hero of the snowy west,” but also created one of the most endearing characters in American fiction.

Yet Kerouac wasn’t the only one. Cassady also appears in John Clellon Holmes’ “Go,” Tom Wolfe’s “The Electric Kool-Aid Acid Test,” Ken Kessey’s “One Flew Over the Cuckoo Nest” and his “The Day After Superman Died,” and also in Hunter Thompson’s “Hell’s Angels.”

Songs have also been written about Cassady, including ones by the Grateful Dead, the Doobie Brothers, Tom Waits and Fatboy Slim.

Nine films have been about or feature Cassady, including 1980s “Heartbeat” and this year’s “On the Road.”

For all of his influence on the Beat Generation and others, Cassady never had anything of his published in his lifetime. He died in 1968, freezing to death on a deserted railway track in Mexico. Kerouac died a year later. In 1971, “The First Third” was published, containing Cassady’s autobiographical writings, and—yes—the “Great Sex Letter.” Allen Ginsberg—who also wrote about Cassady in his poems—marked these deaths as the ending of the Beat Generation; which he even recognized as simply a small group of his friends.