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Cassady was born in Salt Lake City, literally "on the road", as his mother gave birth to him while his parents rode in a car. They later separated, with his father raising young Cassady in Denver, Colorado. He got into trouble often as a boy, and spent part of his teen years in a juvenilefacility. While locked up, he began to write letters back and forth with Hal Chase, another member of the (then-future) Beat Generation. Chase told his friends Kerouac and Ginsberg about Cassady, who wanted to meet him. After he was released, Cassady traveled to New York, marrying sixteen-year-old LuAnne Henderson on the way. He met Ginsberg, and began a homosexual relationship with him (despite Cassady's marriage), and a friendship with Kerouac, recently divorced, who began to teach Cassady about writing. Kerouac's mother, whom he lived with, did not like Cassady, sensing he was just a con artist. Kerouac knew this was at least partly true, but he did not mind, since he enjoyed Cassady's company. They looked a little like each other, and strangers who met them often guessed the two were brothers. They became very close personally, and felt that they really were brothers, though they came from different parents.

Cassady was a restless person, and his wife got tired of him not giving their marriage the attention it needed. She left him, and returned to her family. Cassady soon forgot about her, and started relationships with other women, and also with men. (He and LuAnne got back together later, but their reconciliation did not last.) Before long, he decided he wanted to travel. Cassady was an expert driver, and had no trouble driving cars at over 100 miles per hour, over long stretches of highway. Kerouac left his mother behind, and joined Cassady on many road trips, across the United States and even into Mexico. When Kerouac got sick in Mexico City, Cassady could not wait for him to get better, and left Kerouac behind at a hospital. Kerouac had to find his own way home, and was angry at Cassady, while Kerouac's mother thought it just proved her suspicions about him. Cassady turned up later, asking Kerouac's forgiveness, which he gave him. Good or bad, Kerouac's experiences with Cassady were what he needed to finish a novel about cross-country travel, which he had wanted to write for years.

Kerouac was now married again, to Joan Haverty, and in trying to explain his friendship with Cassady to his new wife, he typed a long narrative, using a roll of teletype paper so he did not have to stop to change pages. He spent three weeks working on the narrative almost non-stop. It became the manuscript for his new novel, which he called On the Road. His wife was bothered by the fact that he spent more time working on the manuscript than with her, and separated from him not long after it was finished. Kerouac spent the next six years making changes and improvements to the manuscript, until a publisher agreed to print it as a book. Cassady's name was changed to "Dean Moriarty", to make the book appear more fictional than it really was. Kerouac delivered one of the first printed copies of On the Road in person to Cassady, who did not give Kerouac the reaction he expected. Instead of being happy and proud, Cassady seemed disturbed and scared, by knowing that part of his life was now in print, and his characterdocumented for the public to see.

On the Road was published in 1957, and it made both Kerouac and Cassady famous. It did not do much to help their personal lives, however. Both men suffered from public overexposure, as the book became a best-seller. A mistake on the book's jacket made readers think that both men were much younger than they were. Their adventures in the book had happened years earlier, but many people thought they were recent. Some readers wanted to travel with them, or invite them to wild parties, or have sexual intercourse with them. Cassady enjoyed the attention for awhile, but it took its toll on him personally. Fame did not help his second marriage, to Carolyn Robinson, or the family they had together. Kerouac himself hated all the attention he got, and spent most of his time at home with his mother, working on new books, or drinking alcohol. In time, he became an alcoholic, and it ruined his health.

Cassady also partly inspired Allen Ginsberg's Howl, and was mentioned in the poem as "N.C.", the "secret hero" of Ginsberg's latest writings. Howl became a landmark work of the 1950s, and added to Ginsberg's and Cassady's fame. Ginsberg handled fame more easily than either Cassady or Kerouac, and had a long public career.

Cassady himself wanted to become a writer, or a jazz musician, but he was not a success at either. He tried to take saxophone lessons, but did not stay with them very long. He mostly worked as a laborer or a brakeman on railroads, before and after On the Road was published. Some of what he did write was published as a memoir, titled The First Third, but it was his only book. He was more successful at writing letters to friends. One was about his seductions of different women during a train trip. He recorded long talks with Kerouac and Carolyn, about their lives and thoughts, and parts of these went into a later book by Kerouac, titled Visions of Cody. ("Cody Pomeray" became Cassady's new fictional name, as Kerouac changed publishers.)

Cassady also sold marijuana to help pay his bills. One customer turned out to be an undercoverpoliceman, who arrested Cassady. He spent a long time in jail. Carolyn had to both work, and try to raise their children alone.

Freed from jail, Cassady began to travel again. During the 1960s, he joined Ken Kesey's Merry Pranksters, who traveled back and forth across the United States in a bus, holding "acid tests", a name for LSD parties. Cassady drove the bus. He acted as merrily as anyone, and as full of energy as a young man, when the Pranksters were around. In private, though, he was not enjoying his life, and old friends noticed he looked very tired.

Cassady had tried to commit suicide a few times when he was younger, and was unhappy. Once he tried to freeze himself to death, waiting outside in cold temperatures during a car trip, but it took too long, and he got back in the car. Early in 1968, while revisiting Mexico, he was found lying alongside a railroad track, where he had been for a long time. Exposure to harsh weather caused his death, just days short of his 42nd birthday. Nobody knew if he was trying to kill himself or not, this time. A few people who knew him felt that he wanted to die, and had for awhile as he got older, and that Cassady finally got his wish.

Cassady left an indelible mark on the world of the 1950s and 1960s, through his documented adventures in the works of Kerouac, Ginsberg, and their friends. He also turned up in Kesey's writings about the Merry Pranksters. He inspired later bohemian characters, like Jim Morrison of The Doors. People today still read about his life and times, and wish they were able to meet Cassady, or make friends with him. The people who knew Cassady remembered him fondly later, even if he let them down personally, because he was such a unique (special) person. People loved watching Cassady live his life to the fullest, while he encouraged them to do the same with theirs.