Guess what I'm writing. A fantastic science fiction novel about a super future world city so immense it's inconceivable—you'll see. Very funny. All worked out. Finish it in a month. 
But the novel never came to pass. Instead, by May of the following year, Jack had produced a 10,000 word short story that he called "cityCityCITY." In a letter to Allen Ginsberg in July 1955, Kerouac wrote:
cityCityCITY is my big science fiction phantasy preview of city & future which I sent Bill [Burroughs] a copy of, very wild, I tell you about it when I see you, very hip, very tea-head writ, sinister, etc., not Burroughsian at all, tho—sort of thing I could do ad infinitum on weed—wrote it during Army McCarthy hearings and so it has wildly hip political flavor. . . . Kafkaen [sic] horror etc. 
On the surface, "city" is a classic 1950s American paranoic sci-fi tale. Kerouac depicts a post-apocalyptic future Earth where:
every square inch was covered with electrical steelplate. The ocean had long ago been covered with earth acquired from surrounding planets. cityCityCITY was the world; every square inch of the world steelplate was covered with the Three Types of Levels of cityCityCITY. You saw the skyline, of steel skyscrapers, far away; then beyond that, like a ballooned imitation of the same skyline, rising way beyond and over it, vastly larger, the second of cityCityCITY, the City level; beyond that, CITY, like a dim cloud, rose huge on the horizon a vast phantasmal skyline so far away you could barely see it, yet it rose far above the other two and far beyond. 
"Master Center Love" (MCL) ("which had for centuries emanated from the inner core of the High Women of the world") controls this new world. Children are born in central facilities and distributed to "parents" in "Zone Blocks" assigned by MCL's "Computer of Infinite Merit." The world is divided into billions of these Zone Blocks, each comprising "only about" 2,500 people. The "horror" (as Kerouac put it) at the core of this society is made clear:
Population kept increasing continually. It was necessary at intervals to electrocute entire Zone Blocks and make room for a new group culled from slags and miscalculations in the system.
(Hence the conducting steelplate!)
The central image of the story, a vision of the Earth inevitably becoming overpopulated and overdeveloped, is attributed by Allen Ginsberg to Kerouac's stay in Richmond Hill, Queens, in the early 1950s:
We used to walk over to the Van Wyck Expressway, which was around the corner from Jack's house. . . . The two of us would stare down at the sunken highway, this bowling alley of cars, and Jack would talk about how he thought it was terrible that they could run a highway like this through a neighborhood and ruin it. He later wrote a manuscript about this called CITYCitycity. 
Even after the story had been written, a passage in Kerouac's 1962 novel Big Sur alludes to his frame of mind at the time of its creation:
Soon we're set straight and pointed head on down beautiful fourlane Bayshore Highway to that lovely Santa Clara Valley—But I'm amazed that after only a few years the damn thing no longer has prune fields and vast beet fields like at Lawrence when I was a brakeman on the Southern Pacific and even after, it's one long row of houses right down the line 50 miles to San Jose like a great monstrous Los Angeles beginning to grow south of Frisco. At first it's beautiful to just watch that white line reel in to Willie's snout but when I start looking around out the window there's just endless housing tracts and new blue factories everywhere—Sez Dave "Yes that's right, the population explosion is gonna cover every bit of backyard dirt in America someday in fact they'll even have to start piling up friggin levels of houses and others over that like your cityCityCITY till the houses reach a hundred miles in the air in all directions of the map and people looking at the earth from another planet with super telescopes will see a prickly ball hangin in space—It's like real horrible when you come to think of it, even us with all our fancy talks, shit man it's all millions of people and events piling up almost unimaginable now, like raving baboons we'll all be piled on top of each other or one another or whatever you're sposed to say—Hundreds of millions of hungry mouths raving for more more more. . . ."
As might be expected, Kerouac eschews the conventions of "plotting" and "character development" in "city," and he instead gives us a great deal of telling without much showing. The story centers on a boy named M-80 whose (surrogate) father T-3 happens to be "Prime Minister" of their Zone Block. As Prime Minister, T-3 is the first to hear when his Zone Block has been nominated for electrocution. This provides an opportunity to do something to help M-80 escape his normally inevitable fate.
What sets this story apart from other contemporary science fiction is Kerouac's incorporation of some of his preoccupations at the time, most notably perhaps that of Buddhism. M-80, despite being only 13, lapses into a distinctly Buddhist frame of mind after having escaped a fiery death on board a rocket into the cosmos:
As he went higher and higher his thoughts grew lighter and more ethereal and finally he had no more thoughts and woke up only after a long time in the pitch darkness of some outer chillicosm, realizing that it had all been like a great sad dream, a vision in the mind—that it was only what it was—"Whether as worlds and cities and universes, or whether as nothingness and emptiness, what difference does it make?"
Kerouac's empathy with those that chose to opt of the consumer society is reflected in his inclusion of the "Loveless Brothers," individuals who spurned the temptations that "cityCityCITY" had to offer but in return could function (almost) independently from it. However, as in his own day, these people were vilified by others in the community.
Ultimately, "cityCityCITY" serves to emphasize Kerouac's oft-expressed view of his own society as a rampant machine, blindly driven by a military-industrial complex, in which people exist merely to power the machine in return for the consumption of its output. The overt means of control in the story simply reflect the covert methods he perceived in his own time and place.
There are few concessions to the reader in this piece, a policy which isn't as successful here as it is in his main body of work. The end result is often a dense avalanche of detail, requiring repeated readings in parts, and even then some difficulties remain.
Possibly because it was "tea-head writ," "city" contains a number of apparent internal and technical inconsistencies. For example, the physical arrangement of the world is hard to visualize based on its description, and how the people living on higher levels of the society away from the electrified steel plate are dispatched once their times come is not explained.
Despite the story's air of underdevelopment and its relative inelegance, the grey and authoritarian world that Jack built has impact. In a sense, "city" is more of a blueprint for this future world than a story in itself: perhaps it is a set of personal notes for Kerouac. This makes sense when we consider that as soon as Jack completed the manuscript in May 1955, he made the following request to William Burroughs, who was at that time living and writing in Tangiers, Morocco:
. . .in the middle of the night, when the orange moon sheds dips from big glory clouds and you dont [sic] hear even a dog bark, and I sit in dark yard in white chair with drink . . . but I'd rather be in the native quarter of Tangiers I tell you.
I'd like to be there high on hash writing "cityCityCITY" copy of short story version of which I am sending you for your pleasure. This is the story that I think we should collaborate on, for a full novel, making the first truly literarily valuable book written by two men (instead of Mutiny on the Bounty)—a real wild one. I think you have there the basic scene for hilarious satires. Your kind and my kind. This present short-story version I hope to publish but it has nothing to do with the eventual novel that I would like to see produced by the two of us in Tangiers or wherever you'll be. By William Lee and Jean-Louis. What say? It'll give me a good reason to go to Tangiers & get high on hash. Read it, send it back, let me know what you think. 
Burroughs' reply on June 9 was ambivalent. Rather than commit to a joint project, he simply advised Kerouac to develop the story by concentrating "on specific characters and situations involving them" . Jack was also told to forward "the rest of it as you get it done."
The collaboration never happened. The reasons why are not clear. The pair had in fact already produced a "Burrouac" (or "Kerroughs!") novel in 1945, when Burroughs was 31 and Kerouac just 23. The work was eventually titled And the Hippos Were Boiled in Their Tanks; it was their account (with the authors writing alternate chapters) of their associate Lucien Carr's murder of David Kammerer in New York in August 1944. This novel was never published, though an excerpt eventually appeared in the 1999 Burroughs anthology Word Virus . Burroughs doesn't appear to have been impressed with their joint effort (nor Jack come to that), despite his well-documented fascination with literary collaboration.
It's curious to observe that Kerouac didn't choose to develop the story himself, following his rejection by Burroughs. This may be connected to the reason why he felt the need to bring Bill on board in the first place. A lack of confidence in his ability to write in a truly creative way, perhaps?
"city" is certainly an anachronism in the context of Jack's other writings, both in terms of its subject matter (perhaps his one genuine work of fiction?) and its ungainly presentation. Why did Kerouac appear to suddenly immerse himself in science fiction, when hitherto (and afterwards) the scope of his attentions had been strictly personal?
In 1954, Kerouac had reached a state of desperation over the fact that no publisher had been prepared to accept any of the autobiographical novels (including an early version of On the Road) that he'd written using the "spontaneous prose" method he'd developed in 1951. (The more conventional The Town and the City, written in the late 40s, had been published in 1950.) He certainly needed money at that point, so perhaps he saw "cityCityCITY" as an opportunity to try to tempt publishers in other ways, with one eye on the possibility that a novelization with Burroughs could be a winner.
Despite having had a full three years of practice at his new style, "city" lacks the fluidity and consistency that are the hallmarks of some of the novels written in the intervening period. Could this have been because he was no longer writing about the people and situations he'd personally experienced and was therefore not able to draw upon his own memories or notes? He was having to create everything from scratch (a potentially stifling position to be in for Kerouac).
Maybe, with his mind on working with Burroughs in the future, he viewed the development of the short story as no more than the first step of a process, and treated it as such. We must also concede that the particular stimulant used during the story's creation could have been a significant factor in the text's final shape.
Whatever the reasons, the fact remains that no novel was forthcoming, and it was to be another four years (post-On the Road) before publication of the short story was accomplished. Nugget magazine published "cityCityCITY" as "The Electrocution of Block 38383939383" in 1959 (some sources cite simply "The Electrocution" as its title there). It was to be reprinted as "CITYCitycity" in 1963 in LeRoi Jones' compilation The Moderns.
In May 1955, Jack sent Malcolm Cowley (the Viking Press editor who was to be instrumental in bringing On the Road to publication in 1957) a copy of the "city" manuscript asking him to try to place it somewhere , but Cowley replied on June 7 reporting a lack of success. More false starts followed.
Today, "cityCityCITY" can be read in the revised edition of Good Blonde & Others . The version printed in Good Blonde differs from the one that surfaced in Nugget and The Moderns (apart from the restoration of Kerouac's original title); it has an ending that extends the piece by a couple of pages. According to editor Donald Allen's notes, this extended version in his book is taken from the original manuscript that was sent to him by John Sampas, executor of the Kerouac literary estate, following Kerouac scholar Dave Moore's suggestion for its inclusion.
What's not clear is who determined the earlier shorter appearances of the story, which Dave Moore reports end with the words: "Therefore the ten second rule is imperative to our Machine." The additional pages certainly don't sit easily with the rest of the text. In January 1957, Kerouac wrote to Sterling Lord, his literary agent, asking for the return of his city (and Mexico City novel Tristessa) manuscripts because "I have to add to them. . ." . It's possible he originally wrote the shorter version (which is the one that got passed to Malcolm Cowley in 1955), then later on decided it needed the extension. On the other hand, he could have completed the longer version in 1955, with the ending being subsequently cut by Nugget; it is admittedly weak.
If Kerouac did add anything to the original in 1957, as he wrote he would do, where is the manuscript that shows this second extension? Perhaps, rather than "add," he subsequently chose to prune in 1957, and this revised manuscipt was the version that ended up in the hands of Nugget.
Whatever its shortcomings, "cityCityCITY" is the kernel of an entertaining and stimulating novel (as Kerouac himself foresaw), possibly even a movie. Its relative obscurity has meant that the particular facet of Kerouac's creativity it represents has remained largely unknown, perhaps coming as a surprise to those who experience it for the first time. One day, hopefully, the story will receive the exposure its potential deserves.
 Published in Jack Kerouac: Selected Letters 1940-1956, edited by Ann Charters, Viking Penguin, New York, 1995.
 "cityCityCITY," published in Good Blonde & Others, edited by Donald Allen, Grey Fox Press, San Francisco, revised edition 1996.
 "The Wizard of Ozone Park," Patrick Fenton, DHARMAbeat #8, 1997.
 Word Virus: The William S. Burroughs Reader, edited by James Grauerholz and Ira Silverberg, Grove Press, New York, 1999.
 Published in Jack Kerouac: Selected Letters 1957-1969, edited by Ann Charters, Viking Penguin, New York, 1999.