It is astounding to think that one of the most influential figures of the artistic culture of the 1950s and 60s was a man who never published a book—at least in his lifetime—or wrote a song. He didn’t play an instrument nor did he draw any headlines pertaining to himself. But even with that lack of mainstream recognition, Neal Cassady served as a creative muse for the circle of Beat writers all the way through the psychedelic era of the Grateful Dead. They say flames that burn twice as bright burn half as long, and Neal Cassady’s seemingly-eternal flame died out on February 4th, 1968, when he succumbed to exposure beside the railroad tracks in San Miguel de Allende, Mexico.

Even the circumstances of Cassady’s death read like a vignette out of Jack Kerouac‘s groundbreaking 1957 novel On The Road. Part of this can be attributed to Cassady serving as the basis for the novel’s captivating character of Dean Moriarty. This train-hopping, benzo-popping madman behind the wheel etched Cassady into the annals of American history forever and served as a guidepost for the nation’s budding youth dreaming of wild adventures on the road.

Born Neal Leon Cassady on February 8th, 1926 in Salt Lake City, UT, Cassady spent much of his early life on the streets with his father. A child of the depression born to a louse of a father, the two traveled the country together as his father scrimped together a life of meager existence. It was during these traversings of the country that Cassady became intimately familiar with its geography as well as the practice of train-hopping. Eventually, however, Cassady developed a taste for personal travel and became an avid car thief, which landed him in and out of reform schools throughout his adolescence.

It was during a trip to New York City in 1946 to visit a friend when he fell in with an aspiring crowd of literary types at Columbia University, among them were now-famous Beat figures Jack Kerouac and Allen Ginsberg. Cassady persuaded Kerouac to teach him to write fiction, a passion that would ultimately go unfulfilled. His second wife, Carolyn, is quoted as saying,

Neal, having been raised in the slums of Denver amongst the world’s lost men, [was] determined to make more of himself, to become somebody, to be worthy and respected. His genius mind absorbed every book he could find, whether literature, philosophy or science. Jack had a formal education, which Neal envied, but intellectually he was more than a match for Jack, and they enjoyed long discussions on every subject.

But it was not through his own writings that Cassady would achieve lasting immortality, but rather that of his friends. He would go on to play a role in works by Kerouac, Ginsberg, John Clellon Holmes, and more. Yet as the Beat Generation grew older and somewhat tamer, time could never extinguish Cassady’s spirit and by the beginning of the 1960s he would find himself at the epicenter of yet another cultural revolution.

With On The Road serving as a literary guidebook for millions of youth across the country, Cassady had already become a cult figure for young Americans as the 1950s transitioned into the 60s. After a brief prison stint and a divorce from his second wife, Cassady shared an apartment with Ginsberg and poet Charles Plymell in San Francisco where the hippie revolution would soon take hold. Before long, Cassady had fallen in with another emerging literary figure—Ken Kesey—and became a fixture of The Merry Pranksters‘ early Acid Tests. Cassady’s role as the driver of The Pranksters’ Furthur bus during their now-legendary 1964 cross-country trek would be immortalized in Tom Wolfe‘s seminal 1968 book, The Electric Kool-Aid Acid Test. Through his association with Kesey, The Pranksters, and even the Hell’s Angels, Cassady would cross paths with the Grateful Dead.

Guitarist Jerry Garcia has widely credited On The Road as an early artistic inspiration in his life, so he was no doubt elated to meet the star of the novel. The Dead even opened their home to Cassady and at one point the eccentric shared a closet room with nubile Bob Weir at the band’s 710 Ashbury residence.

As the 1960s slouched to a close, however, Cassady once again found himself at the turning point of history. By 1968, the hippie movement had been turned into a commercial farce and the Haight-Ashbury district overrun by yuppies. Cassady responded by increasing the speed and frequency of his travels and attempting to find solace once again on the open road. It was on February 3rd, 1968 that he attended a wedding party in San Miguel de Allende, Guanajuato, Mexico. In his memoir Cronies, fellow Merry Prankster Ken Babbs writes that Cassady was egged into counting the railroad ties between there and the next town.

Neal was all for it but the others were jacking him around and didn’t follow through. Neal was disgusted—agree to do something and then not do it?—and struck out on his own—bareheaded, short-sleeved shirt, thin windbreaker, chino trousers, worn-out leather shows—into a cold, misty night, water dropping off the trees and bushes.
They found him at down, lying on the tracks, a half-mile from the party. They tried to rouse him but could only get a slight quiver from his body.
“His lips are moving,” one of the guys said.
They bent in close.
“Sixty-four-thousand-nine-hundred-and-twenty-eight,” Cassady murmured. 

Cassady died four days later, four days shy of his 42nd birthday.

In an eerie turn of the kind of fate that defined Cassady’s life, hundreds of miles away in California Bob Weir was finishing up the lyrics to his first songwriting endeavor, “The Other One”, which name-checks Neal, on the day that Cassady died—unbeknownst to any of his stateside friends. In a short story published in Esquire in 1979, Ken Kesey details a fictionalized account of Cassady’s final hours under the name, “The Day After Superman Died”.

Cassady was a fixture at the Grateful Dead’s early San Francisco concerts, and it wasn’t uncommon for the loquacious cult-hero to seize control of the microphone. Here he is delivering a frenzied rap on July 23rd, 1967 at the Straight Theatre in San Francisco.

Grateful Dead – Neal’s Rap – San Francisco, CA – 7/23/67

[Video: Mark Scalise]

Jerry Garcia Talks About Neal Cassady

[Video: Jon Bonner]

Rest easy, Cowboy Neal.