In Chapter 1, our narrator, Ray Smith, is resting on a gondola car en route from Los Angeles to Santa Barbara. A "thin little old bum" soon joins him on the car and the two silently ride together as they attempt to keep warm in the cold train. While the train is stopped, Ray asks the bum to watch his pack while he runs to a nearby store to buy wine, bread, and candy. Upon returning and noticing the old man's pitiful supply of sardines, he offers him more food and contemplates the Buddhist conception of charity mentioned in the Diamond Sutra. The narrator, who is speaking from the future, comments that he is now more cynical about such notions. The bum ignites a brief conversation by showing Ray a small prayer to Saint Teresa that he carries around, and then the duo part ways at a crossing. Alone on the beach, Ray cooks himself a meal of packaged foods and wine while contemplating the vastness of the universe and the experience he has just had. He records the thoughts and dreams he has as he drifts in and out of sleep.
Ray connects the first chapter to the second, which occurs later in the future, by drawing a parallel between the old man he has just mentioned and his more recent friend Japhy Ryder: he calls them both "Dharma Bums." The focus is then on Japhy, whose life is outlined from his childhood in the woods of Oregon through his college days and his eventual blossoming as an Oriental scholar. Ray recounts a fabulous event in which a beautiful blonde wearing a bathing suit, in exchange for Benzedrine, drove him to San Francisco: it was there he saw Japhy for the first time walking with a knapsack on his back.
The rest of the chapter is devoted to describing a raucous night that he and Japhy share, beginning with a drug-filled party at a bar called "The Place." Among a crowd of stereotyped poets, Japhy, who is wiry, dressed in secondhand work clothes and sporting a goatee, seems out of place, but Ray admires his poetic skill. Before the reading starts, the narrator observes that he only focuses on two facets of Buddhism ("All life is suffering" and possibly "The suppression of suffering can be achieved") and feels that Japhy's esoteric, scholarly knowledge is meaningless.
The poetry reading takes place at "Gallery Six," where Alvah Goldbook (modeled off of Allen Ginsberg) recites "Wail" (Ginsberg's "Howl") and Japhy rouses the audience with his straightforward poetry. Aforementioned poets, each with their own style, perform, as Ray riles everyone up and generally enjoys himself. Later, the rambunctious crowd head over to a restaurant in Chinatown, where Ray asks one of the cooks a question about a particular Buddhist. Japhy believes that the cook's answer, "I don't care," is "Perfect...absolutely perfect," adding "Now you know what I mean by Zen."
The third chapter, which occurs at an unspecified time in Ray's life, is also primarily about Japhy. Ray is living in a cottage in Berkeley, California, with poet Alvah Goldbook. Although his residence is modest at best, he is also clearly fond of it and describes it with a sentimental relish. Japhy, a minimalist, is living a mile away in a tiny shack that includes little other than straw mats, crates that serve as a table, cooking utensils, unused Japanese shoes, and books (which, Ray notes, are the only valuable things he owns). Even his clothes are old hand-me-downs.
When the narrator goes to visit his companion, he finds him sitting on a straw mat, sipping tea and translating Han Shan's poem "Cold Mountain." Japhy makes Ray some green tea before telling him about Han Shan, a non-conformist who writes about his lonely journey climbing a frigid mountain. Ray does not understand why his friend has translated the poem so elaborately and loosely, but Japhy explains that he needs to make it clear and passable to fellow scholars. The two agree that, in spirit of Han Shan, they should go on a mountain climbing expedition; in fact, this journey does occur in upcoming chapters.
The narrator notes that his friend looks remarkably melancholy and asks if he has been meditating today. Japhy confirms Ray's suspicion and tells him that he actually meditates daily, although certain people interrupt him: a girl, with whom he plays something mysteriously referred to as "yabyum," as well as Rol Sturlason, who happens to show up then to discuss his upcoming trip to Japan. At the end of the chapter, Rol explains the existence of the Ryoanji rock garden, mysteriously arranged so as to be "mystically aesthetic." The narrator does not fully appreciate or understand this discussion, but notices Japhy's philosophical serenity and how different this visit is from the night of the poetry reading.
In Chapter 4, Ray, Warren Coughlin, and Alvah Goldbook decide to buy some alcohol and visit Japhy. Coughlin points out that Japhy has two sides: he is a quiet, wandering bicyclist, but his friends also remember his rowdy, bacchanalian party days at Reed College.
When the trio shows up, Japhy, who is reading a book of American poetry, suddenly produces a knife, yawps, leaps violently, and runs toward Ray, who is holding the jug of alcohol. Ray instantly believes Japhy is angry with them for interrupting his studies, but surprisingly he grabs the jug and immediately begins to drink it. The four men then talk merrily for several hours about such things as poets and poetry; Ray offers readers a "sample" of their conversation.
The night ends when the three friends stagger home, drunk, boisterous and happy. Ray confesses that he feels guilty for ruining his friend's studying until the next night, when Japhy shows up with a girl and tells her to take her clothes off.
Chapter 5 begins with Ray and Alvah sitting quietly, drinking tea and reading poems. Japhy and the girl (named Princess) arrive on bicycles. Ray realizes that he forgot to mention that Princess in fact came over to Japhy's shack after Rol Stuarlson (which occurred in Chapter 3) and seemed incredibly unruffled - even pleased - with his sexual comments. The narrator, who confesses that he had met Princess - and been infatuated with her a year ago - naively agrees to be shown "yabyum." When he comes back with a bottle of wine, he is shocked to find his three companions in various stages of undress.
Japhy and Princess sit steadily facing each other as Japhy explains the rite of yabyum, a holy ceremony in Tibet. Ray, though, continues to be appalled, especially when the three of them begin to engage in sexual activity. Ray, torn between his enormous desire for Princess and his devotion to abstinence, eventually succumbs to temptation and begins to kiss Princess's hands and arm. After yabyum, Ray and Princess bathe together and it is determined - to everyone's delight - that this should be a weekly ritual.
Princess claims that she is a Bodhisattva - "the old mother of the earth" - and Japhy fully supports her, spouting academic and historical jargon, as he condemns America for its stringent constraints on sexuality. Afterwards, Ray and Alvah discuss Japhy and determine that he is brilliant, speculating about where he will end up; they believe he can do anything.
That night, when Ray is in the yard looking up the stars, Alvah, who cannot sleep, comes and joins him. The two get into an argument: Ray disparages Alvah for living in what he feels is an "illusory" physical world, while Alvah retorts that the physical world is certainly more real than the abstruse mumbo-jumbo that Ray believes in. Eventually, Alvah departs in a huff, but Ray calms himself with the assurance that the fight was not "real." As he falls asleep, he vehemently denies his desire for Princess.
The very first sentence of The Dharma Bums is quite revealing. It reads, "Hopping a freight out of Los Angeles at high noon one day in late September 1955 I got on a gondola and lay down with my duffel bag under my head and my knees crossed and contemplated the clouds as we rolled north to Santa Barbara." Immediately apparent is Kerouac's unique writing style - simple, relaxed, and conversational. Largely unfettered by punctuation marks or grandiloquent vocabulary, the author's prose mimics the phrasing of a young child who is breathlessly eager to tell a story. On another level, Kerouac's narrator, who writes about "hopping a freight" and "getting on a gondola [car]" as if they are completely natural ways to travel, has already begun to exhibit his own defiant and carefree nature. Finally, the character's pose - resting against a duffel bag as he stares at the sky - suggests a sort of easygoing, dreamy spirituality. Thus, by the end of the first sentence, Kerouac has already managed to set the tone that will underlie the remainder of his novel.
It is important to note, however, that Chapter 1 of The Dharma Bums contains a lengthy passage that is not only antithetical to the rest of the book, but, if taken seriously, disturbingly undermines all that is to come. Ray, who is narrating this story from the future, sadly comments that "I've become a little hypocritical about my lip-service and a little tired and cynical....But then I really believed in the reality of charity and kindness and humility and zeal and neutral tranquillity and wisdom and ecstasy...at this time I was a perfect Dharma Bum myself and considered myself a religious wanderer." This contrast between "then" and "now" is striking. Kerouac's "laundry-list" of virtues is practically parodic; he sounds like a hardened adult chuckling about his silly childhood dreams. There are no other passages like this in the rest of the novel-it ends on an extremely idealistic note. Eerily, though, it foreshadows the cynicism that Kerouac's himself would develop later in life.
After the narrator, the first character that Kerouac describes is a bum who is modest and religious, meek and frugal, "the kind of thin quiet little bum nobody pays much attention to even in Skid Row." Ray is charitable toward him because he feels pity toward him, but will eventually learn from Japhy what it is like to "give for the sake of giving;" the first old bum thus serves as a marker for the "starting point" of Ray's journey into Buddhism. However, Kerouac's immediate mention of a likable "Dharma Bum" who is quiet, pitiable and harmless, also serves the purpose of setting up the novel's structure with rebel/outcasts as worthy heroes, pitted against unforgiving cops and a biased public.
After the introductory chapter, Kerouac jumps right into the heart of all aspects of Beat lifestyle, from drunken poetry-parties to solitary study and meditation. Here is Kerouac's first introduction of the concept of simplicity as happiness, when Ray repeatedly describes the run-down dwelling place he shares with Alvah Goldbook as ideal: "We had a perfect little kitchen with a gas stove, but no icebox, but no matter. We also had a perfect little bathroom with a tube and hot water..." Japhy's dual nature as rowdy party-goer and quiet scholar is also made very explicit in these first five chapters. When his friends come over with a bottle of wine, he is in the middle of studying with a cup of tea; but then again it is Japhy who interrupts his friends' teatime by bringing Princess over for yabyum.
The beginning of the book also includes a number of telling lines that reveal Ray's strange attitude toward Japhy. He at first describes the man with obvious admiration, from his "strong and wiry and fast and muscular" body to his "eyes [that] twinkle like the eyes of old giggle sages of China. At the same time, though, their conflicts of principle are foreshadowed: "I warned him at once that I didn't give a goddamn about the mythology and all the names and national flavors of Buddhism, but was just interested in the first of Sakyamuni's four noble truths, All life is suffering." Ray's monosyllabic responses to Japhy's discussion about Han Shan and Buddhism are particularly ambiguous and may even reflect sarcasm. Ultimately, he concedes that "I have never met such weird yet serious and earnest people."
In the last chapter of this section, Ray's devotion to celibacy ends with a "tough-guy" self-affirmation that is little more than thinly veiled denial. Ray's overly-rough diction - "I wasn't taken in by no Princess or no desire for no Princess and nobody's disapproval" - is itself proof that he is trying desperately to ignore his own urges and is a clear example of pragmatism in The Dharma Bums; in other words, it demonstrates that Ray believes whatever he feels he ought to believe in order to get through life as smoothly as possible.