Neal Cassady was the literary icon who never finished a book in his life. But his life inspired some of the craziest characters ever written.
1. He Inspired Everyone—Except Himself
Neal Cassady was the free-wheeling, frenetic, hedonistic “Holy Fool” that inspired (and slept with) some of the Beat Generation’s most iconic writers. He was the man behind Jack Kerouac’s character, Dean Moriarty, in On the Road. He was Allen Ginsberg’s plaything and Tom Wolfe’s muse. Sadly, the only person he couldn’t inspire to greatness was himself.
2. He Had A Crazy Origin Story
Neal Cassady was born in February 1926 to Maude Jean and Neal Marshall Cassady in Salt Lake City, Utah. Over the course of the next four decades, he would embark on some of the wildest road trips and adventures with his literary friends.
You might say that he was born with an innate passion for the open road and unbridled freedom—and few people can survive that path for long.
Library of Congress, Wikimedia Commons
3. He Was Always “On The Road”
Road trip novels such as On the Road and The Electric Kool-Aid Acid Test would, one day, immortalize Cassady’s hedonistic lifestyle. But his first road adventure happened long before that. According to our sources, Cassady was born in the back of a bus while his parents were traveling through Salt Lake City. The road ahead would be a bumpy one.
GrawLIN, CC BY-SA 4.0, Wikimedia Commons
4. He Grew Up On Skid Row
From the very beginning, Cassady was in for a difficult life. The first real tragedy of his life came when he was just 10 years old, when his mother suddenly passed away. From then on, he would be in his father’s alcohol-hazed care. He grew up with his dad on Denver, Colorado’s skid row—but at least he had a colorful cast of characters to look out for him.
Ted Streshinsky Photographic Archive, Getty Images
5. He Had Many Surrogate Fathers
Growing up in lower downtown Denver, Cassady found himself surrounded by hardened men. But by being the youngest amongst these grizzled men, he “presented a replica of childhood” and many of them thought of him as their own son. However, none of them exactly give him a good example to follow.
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6. He Was On The Wrong Side Of The Law
Growing up on skid row, Cassady learned to live on the wrong side of the law. He had his first of many run-ins with the authorities when he was just 14 years old after the Denver fuzz picked him up for petty thievery. But, by the very next year, he had already upped his game. At the age of 15, he boosted his first car.
Too bad he didn’t drive well enough to get away.
Unknown Author, Wikimedia Commons
7. He Liked Boosting Vehicles
Apparently, two early run-ins with the law weren't enough to straighten Cassady out. Shortly after boosting his first vehicle (and getting caught), he boosted another one. This time, the law also pegged him for fencing pilfered goods.
He would need a better role model than the troubled men on Denver’s skid row if he was going to become a respectable man—or, at least, something close to one.
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8. He Found A Good Role Model
Cassady finally found the exemplary male role model that he had always lacked. Or so he thought. Around the age of 15 or 16, Cassady met the highly-regarded lawyer and educator, Justin W. Brierly. Brierly, 21 years Cassady’s senior, was a prominent figure in the community. But he wasn't as innocent as he appeared.
9. He Learned To Read And Write
Despite his troubles with the law, Cassady impressed Brierly with his raw intellect and hard-earned street smarts. Brierly then tried to set Cassady on the straight and narrow. He taught him to read, enrolled him in a good high school and gave him every opportunity that a teenage boy would need to become a respectable man.
He may also have given him some lessons that he didn’t need.
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10. He Had A Big “Sledgehammer”
It might not have been Cassady’s massive intellect that originally impressed Brierly and drew the older man to him. Later writings from Jack Kerouac and Allen Ginsberg mentioned Cassady’s other considerable talents. Namely his, how should we say, considerably above average, below-the-belt “sledgehammer”. Brierly might have been the nail.
Tom Palumbo , CC BY-SA 2.0, Wikimedia Commons
11. He Had An Affair With His Mentor
While Brierly was supposed to be helping the teenage Cassady set his life right, he might actually have been helping himself to Cassady. Allegedly, Brierly was “attracted to Neal”. Some sources suggest that he even managed to “entice” the young man into his bedchamber.
Regardless, Cassady had too free a spirit to walk the straight and narrow Brierly hoped for him.
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12. He Could Write—Really Well
In spite of Brierly’s help—or because of it—Cassady went right back to his old ways. He continued going on joy rides in other peoples’ cars and eventually spent 11 months behind bars. While in the clink, he and Brierly regularly exchanged letters. It was the first sign that he could do more than hotwire cars. He could write—like no one else on earth.
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13. He Went To University But Didn’t Attend
Seeing the promise in his prose, Brierly thought he might introduce Cassady to some of his more erudite and educated friends. In a move that would shape the future of literature forever, Brierly introduced Cassady to Hal Chase. At the time, Chase (another Brierly rescue) was attending Columbia University—alongside some future literary titans.
14. He Met Like-Minded Souls
Cassady visited Chase at Columbia University in 1946. That’s when Cassady, by way of his sheer charm and intellect, changed the course of literary history forever. Chase introduced him to two up and coming writers and fellow free spirits: Jack Kerouac and Allen Ginsberg. For one of them, it was love (or lust) at first sight.
15. His “Manhood” Inspired Ginsberg
Kerouac and Ginsberg had a gift for writing but they lacked inspiration—until Cassady came along. His freewheeling spirit fascinated Kerouac, while his substantial “manhood” impressed Ginsberg. There’s no doubt that post-WW2 poetry would not have looked the same without Cassady. It would certainly have been a lot less raunchy.
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16. He Was Animalistic
Ginsberg in particular took a shine to Cassady, with his winning smile, easy charm, and heavy “equipment”. Famously, Ginsberg exclaimed, “Neal Cassady was my animal”. But, we don’t think he was talking about spirit animals. Cassady unlocked something animalistic and primal in the young Ginsberg that would shape his later writing.
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17. He Was Ginsberg’s Lover
Neal Cassady had always been a hustler. He had a way of charming everyone around him and becoming whatever they needed him to be in order to get what he wanted out of them. In the case of Ginsberg, that meant an animalistic lover. When they met in 1946, they sparked up a torrid physical relationship—one that would last until the bitter end.
18. He Brought Ginsberg To His Knees
Nothing inspired Ginsberg more than his affair with Cassady. Writing about it later, Ginsberg said, “he brought me to my knees/and taught me the love of his [sledgehammer] and the secrets of his mind”. Cassady’s relationship with Ginsberg was just the first in a string of liaisons with literary figures who took everything from him.
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19. He Discovered His True Passion
At first, Cassady also got what he wanted out of his newfound friends. When he wasn’t busy "entertaining" Ginsberg, he was pursuing a new passion. Cassady asked Kerouac to teach him how to write fiction. Turns out, Kerouac had more to learn from Cassady than the other way around—and more to borrow without permission.
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20. He Was Smarter Than The Rest
Cassady had something that his new Ivy League friends did not: street smarts. And lots of it. Cassady’s eventual second wife recalled that “Jack had a formal education, which Neal envied”. However, it was obvious to everyone that “he [Cassady] was more than a match for Jack” intellectually. He was also Kerouac’s literary superior.
He just didn’t know it until it was too late.
21. He Went On A Wild Adventure
With his newfound friends, Cassady embarked on a cross-country journey full of adventure and wild tales. Along with Kerouac and Ginsberg, Cassady piled into a van and sped across the United States, even making it down to Mexico. Cassady picked the destinations (seemingly at random) and Kerouac wrote about it—then cashed in on it.
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22. His Essence Defied Traditional Language
Cassady’s frenetic pace and energy propelled the three men across the country and beyond. More than anything, Kerouac wanted to capture the spirit of their wild and reckless adventure. But, no matter how brilliant his writing sounded, it lacked the unique energy that Cassady gave off. He needed Cassady’s words to capture Cassady’s essence.
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23. He Wrote Breathless Letters
After their trip ended, Kerouac gave up on his mission to turn their adventures into a novel because his formal prose lacked the right tone—but Cassady wasn't finished giving Kerouac inspiration. The group had parted ways once their journey ended but they kept in touch through letters.
Cassady’s letters were exactly what Kerouac needed.
24. His Friend “Borrowed” His Writing Style
Without even knowing it, Cassady had founded a new literary style in his letters to Kerouac. A style that Kerouac was all too happy to “borrow” for his own writing. Kerouac used Cassady’s free-flowing stream of consciousness writing style to finish the novel that he had been writing about their wild road trip escapades.
He never gave Cassady any credit.
MK2 Productions, On the Road (2012)
25. His Friend Claimed All The Credit
Kerouac wrote On the Road “in a rush of mad ecstasy, without self-consciousness or mental hesitation” just as Cassady had written his letters. It was bad enough that he borrowed Cassady’s writing style, but he added insult to injury by basing the central character, Dean Moriarty, off of Cassady himself. It was not a flattering picture.
MK2 Productions, On the Road (2012)
26. He Was A Saint And A Sinner
On the Road turned Cassady into something of a Beat Generation icon. But for all of the wrong reasons. At the start of the novel, Kerouac praised Cassady as “a new kind of American saint”. But, by the time the novel’s true premise became apparent, Kerouac called him a “HOLY GOOF” who was incapable of being a dependable father and husband.
MK2 Productions, On the Road (2012)
27. His Marriage Was Sensational
Kerouac fictionalized a lot of stories about Cassady’s life and got rich in the process. One of the stories that he fictionalized was Cassady’s first marriage. Back in 1945, after Cassady made it out of the clink, he married Lu Anne Henderson. We don’t know much about the marriage except for what Kerouac sensationalized in On the Road.
MK2 Productions, On the Road (2012)
28. He Broke His Thumb Hitting His Wife
In the pages of On the Road, Kerouac painted Cassady as an absentee father and fickle husband and lover to Lu Anne. According to his book, Cassady and Lu Anne fought constantly—sometimes even physically. Allegedly, he severely “splintered” his thumb while engaged in a physical altercation with Lu Anne.
The smears didn’t end there.
MK2 Productions, On the Road (2012)
29. He Showed Off His “Enormous Dangle”
As if it wasn’t bad enough that Kerouac made Dean Moriarty a bad father and husband, he took it a step further. Kerouac further portrayed Cassady as someone obsessed with his “enormous dangle”. He claimed that Cassady used to open doors in nothing more than his socks, just to show it off.
At least some people didn’t mind the show.
MK2 Productions, On the Road (2012)
30. He Was The Perfect American Man
With such an impressive “dangle”, Cassady couldn’t ever stay married to one woman. Shortly after his marriage to Lu Anne, he met Carolyn Robinson, a master's student in theater arts at the University of Denver. Robinson immediately fell for Cassady and called him “the archetype of the American Man”. But he was taken. Well, kind of.
MK2 Productions, On the Road (2012)
31. His Wife Abandoned Him
Under mysterious circumstances that we may never know the true nature of, Lu Anne walked out on Cassady. Thanks to her abandonment, he was able to get an annulment in 1948. Just over a month later, he turned Carolyn Robinson into Mrs. Carolyn Cassady. But she was soon going to learn a very hard lesson: No one could tame the wild Neal Cassady.
32. He Settled Down For A Time
Following their hasty nuptials, Cassady and Robinson moved out to a ranch house in Monte Sereno, California. As they produced three children, it appeared that Cassady had given up on his wild days and was settling into a quiet suburban life. The truth, however, was that his thirst for wild adventures was far from sated.
33. He Still Had A Thing For Ginsberg
Even though he had a wife and family in Monte Sereno, Cassady still kept up his affair with Ginsberg. He was never more than 50 miles away from San Francisco, where Ginsberg lived. Most sources suggest that Cassady preferred the company of women, but something about Ginsberg kept him coming back for 20 long and lurid years.
MK2 Productions, On the Road (2012)
34. He Learned Sharing Isn’t Caring
Ginsberg wasn’t the only thing that Cassady hadn’t given up on in his new suburban life. Even with a family, he still clung to his law-bending (and breaking) ways. In 1958, however, he messed up terribly. At a San Francisco nightclub, he tried to share his grass with an undercover agent. This time, there was no Brierly to bail him out.
MK2 Productions, On the Road (2012)
35. He Was A Bird In A Cage
For a wildly free spirit with bundles of frenetic energy like Cassady, the worst thing imaginable was a life cooped up in a cage. Sadly, that’s exactly what happened after that 1958 incident at the nightclub. Cassady ended up spending two whole years behind bars. By the time he got out, he had too much pent up energy to go back to family life.
Ted Streshinsky Photographic Archive, Getty Images
36. He Needed His Family
Following his release from the clink, Cassady struggled to get his life back on track and provide for his family. Eventually, Robinson saw that the family was too much of a burden for him, so she filed for divorce in 1963. She didn't yet realize what she was doing.
It turns out that his family had been the only thing keeping him from going totally feral.
MK2 Productions, On the Road (2012)
37. He Lost All Of His Self-Esteem
Trying to provide for his family and tame his wilder instincts had actually been good for Cassady. So, when Robinson filed for divorce, she soon realized that she had dashed his last hopes at normalcy and respectability. As she recalled, “this was a mistake and removed the last pillar of his self-esteem”. But at least he was free to hit the road again.
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38. He Embarked On Another Journey
As a free agent once again, Cassady moved in with his old Beat Generation friend and long-time lover, Allen Ginsberg. But there was another writer, Ken Kesey, who was more Cassady’s speed by then, and the two began spending more time together.
It seemed Cassady was gearing up for one last great adventure on the free, open road.
39. He Drove Everyone Mad
Kesey planned a cross-country road trip to attend the New York World's Fair. Of course, Cassady was never one to miss out on a good adventure. Not only did he agree to tag along with the group, but he actually became the mad-hatted driver. It was an out of this world experience that would take Cassady to new “heights”.
MK2 Productions, On the Road (2012)
40. He Was A Merry Prankster
As it turns out, Kesey and his followers were ardent and vocal supporters of psychedelics. As they embarked on their 1964 summer trip across the country, they named themselves the Merry Pranksters. Fueled with all kinds of powerful psychedelics, they drove their van, Furthur, onward to adventure. But Cassady was about to be singing an all-too-familiar toon.
Michael Ochs Archives, Getty Images
41. He Inspired Another Classic
Kerouac had turned Cassady’s misadventures into solid gold with the best-seller, On the Road. This time, it was Tom Wolfe who would immortalize Cassady’s unique energy in the 1968 novel The Electric Kool-Aid Acid Test. Once again, Wolfe borrowed more than just a little inspiration from Cassady to write his masterpiece.
42. He Was A Trained Bear
According to Robinson, Cassady’s friends never truly cared for him. Decades later, she recalled how they “treated him like a trained bear” and handed him all kinds of pills. But Cassady was only too happy to play along. His wife had a theory about that: He was trying his hardest to get himself killed.
Soon enough, he would get his morbid wish.
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43. He Was Never The Bride
Cassady was always the bridesmaid, never the bride when it came to his literary friends of the Beat Generation. He founded the unadulterated literary style that made them all famous but never saw any of the money. That might help to explain one particularly tense situation between Cassady and Kerouac after the latter published On the Road.
MK2 Productions, On the Road (2012)
44. He Couldn’t Look His Friend In The Eye
When the first copies of On the Road hit the shelves, Cassady visited Kerouac. It’s not clear what their meeting was about, but the ending left a cloud hanging over their friendship. As Kerouac recalled, Cassady failed to look him in the eye when he said goodbye that evening.
It was the first time Cassady seemed distant and reserved. Something between them had clearly changed.
45. He Looked Away
Kerouac recalled that Cassady “looked away shifty-like” as he walked away that night. From then on, they grew further and further apart with Kerouac saying, “I couldn't understand it and still don't—I knew something was bound to be wrong”. Maybe if he had just given Cassady the credit he deserved, Cassady’s story might not have ended in tragedy.
MK2 Productions, On the Road (2012)
46. He Was Out Of Control
By 1967, Cassady began spinning out of control. He traveled to Mexico with his long-time girlfriend, Anne Murphy, and George "Barely Visible" Walker (another Merry Prankster). He clearly longed to recapture the frenetic energy and wild adventures of his youth, perhaps to seek inspiration, at long last, for his own writing.
But he was running on fumes—and running out of time.
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47. He Had A Farewell Tour
Cassady spent the next year traveling around the United States and Mexico at a breakneck speed. He visited some of his favorite haunts from San Francisco to New York, visited his eldest daughter to meet his first grandchild, and even welcomed in the New Year with his ex-wife, Robinson.
Sadly, he didn’t know that it was his farewell tour.
San Francisco Chronicle, Getty Images
48. He Was Writing His Masterpiece
Cassady returned to Mexico in early 1968. From the sounds of it, he had finally found the inspiration and the words that he needed to write his own book. He was, by all accounts, hard at work on something of a memoir of his childhood, titled The First Third. Unfortunately, unbeknownst to him, he was already in his final act.
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49. He Slept On The Side Of The Road
In early February 1968, Cassady attended a wedding in San Miguel de Allende, Guanajuato, Mexico. As usual, it looks like he had too much fun and ingested all kinds of substances. He began making his way home but, presumably feeling tired from the party, decided to lie down at the side of the road. It turned out to be his final resting place.
AlejandroLinaresGarcia, CC BY-SA 4.0, Wikimedia Commons
50. He Fell Into A Coma
Wearing nothing but a t-shirt and jeans, Cassady hunkered down for the night at the side of the road and passed out. But then the temperatures dropped and the rain started to fall. Cassady laid there until the next morning when Anton Black, a professor at El Paso Community College, found the literary muse in a comatose state.
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51. He Left So Many Words Unwritten
In a desperate attempt to save Cassady’s life, Black tossed his unconscious body over his shoulder and hauled him to the post office. From there, paramedics rushed Cassady to the hospital. But it was already too late. Just a few hours later, Cassady passed at the age of 41, leaving behind an unfinished manuscript.
52. His C.O.D. Is A Mystery
Cassady’s official autopsy cited “general congestion in all systems” as the cause of his ultimate demise. Others say that he succumbed to exposure, while still others claim that he gave in to kidney failure from an excessive amount of barbiturates in his system. Regardless of the exact cause, Cassady’s real fatal blow was his lack of self-esteem.
Robert Alexander, Getty Images
53. He Could Never Find The Words
In a devastatingly honest and confessional letter to Kerouac, Cassady lamented his own failure to launch as a writer. “My prose has no individual style as such,” he wrote. “There is something there that wants to come out; something of my own that must be said. Yet, perhaps, words are not the way for me”. They might have been—if everyone else hadn’t stolen them first.
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