In the first chapter of Part One, Sal meets Dean and his wife, Marylou, whom he describes with imagery and similes:
Marylou was a pretty blonde with immense ringlets of hair like a sea of golden tresses; she sat there on the edge of the couch with her hands hanging in her lap and her smoky blue country eyes fixed in a wide stare because she was in an evil gray New York pad that she'd heard about back West, and waiting like a longbodied emaciated Modigliani surrealist woman in a serious room.
Kerouac first describes Marylou's hair with a simile: it is "like a sea." Golden tresses are literally descriptive of her hair (a "tress" is a lock or ringlet of hair), but the sea comparison is metaphorical. He goes on to use imagery to help the reader imagine her blank stare, which Sal attributes to her awareness of the "evil gray New York pad" that she's in. Perhaps Marylou is doubting her marriage and the place it has landed her in. "Smoky blue" suggests her eyes have a gray tint to them.
Kerouac often uses words poetically—that is to say, he picks nouns, adjectives, and verbs that don't make sense literally, but do serve a poetic function and concisely give the reader information about the scene. Marylou's "country eyes" are a good example. What would make eyes "country"? A literal interpretation doesn't make sense, but a figurative one might suggest that, because Marylou is from the country, her eyes are not accustomed to sights like New York City.
Finally, Sal uses a simile to compare Marylou to a "longbodied emaciated Modigliani surrealist woman." This is an allusion to Amedeo Modigliani, a modernist painter with connections to Cubists and Pablo Picasso.
In Part 1, Chapter 4, Sal describes hitchhiking to Denver on a truck driven by two young, cheerful farmers. His use of imagery makes the road life more vivid for the reader and establishes the carefree mood that characterizes the best moments of his journeys. He also uses a simile to describe his elation.
The road changed too: humpy in the middle, with soft shoulders and a ditch on both sides about four feet deep, so the truck bounced and teetered from one side of the road to the other [...] How that truck disposed of the Nebraska nub—the nub that sticks out over Colorado! [...] The great blazing stars came out, the far-receding sand hills got dim. I felt like an arrow that could shoot out all the way.
Sal's meticulous description of the road serves to transport the reader to the truck. A reader may not only see the humpy, worn-down road, but also feel its impact on the movement of the truck. Then Sal takes a bird's-eye view of his travels: as if he is looking at a map, he describes the truck moving over the "Nebraska nub." He returns to a terrestrial viewpoint and uses a simile that indicates his excitement at traveling. He is "an arrow that could shoot out all the way"—something that has the potential to move quickly. Notice that he says "could," rather than saying he is an "arrow that has shot out all the way." That choice of verb tense emphasizes that his journey is only just beginning.
In Part 1, Chapter 8, Sal tries to sleep, but Dean and Carlo's extended conversation on philosophy keeps him awake. Dean and Carlo metaphorically call their talking a "machine," and Sal plays with this characterization, turning it into a simile:
"Stop the machine," I said. They looked at me.
"He's been awake all this time, listening. What were you thinking, Sal?" I told them that I was thinking they were very amazing maniacs and that I had spent the whole night listening to them like a man watching the mechanism of a watch that reached clear to the top of Berthoud Pass and yet was made with the smallest works of the most delicate watch in the world.
Dean and Carlo's abstract conversation is so incessant that they call it a machine. It seems the two men have become fast friends. Sal, who cannot sleep, asks them to "stop the machine." When they ask his opinion of their conversation, he instead responds, perhaps sarcastically, that they've impressed him: listening to their conversation, he says with a simile, is like watching a fantastically huge yet intricate watch operate.
The Berthoud Pass is a route over the Rocky Mountains in Colorado. As usual, Kerouac sprinkles his prose with allusions to American landmarks and people. This allusion also suggests that Sal has done some traveling across America before the events of On the Road.
When Sal climbs a mountain in San Francisco, toward the end of Chapter 11 of Part 1, he describes what he sees with personification, imagery, and metaphorical language.
And before me was the great raw bulge and bulk of my American continent; somewhere far across, gloomy, crazy New York was throwing up its cloud of dust and brown steam. There is something brown and holy about the East; and California is white like washlines and emptyheaded—at least that's what I thought then.
Phrases such as "raw bulge and bulk of my American continent" are excellent examples of Kerouac's style. This description is part literal, part metaphorical: America does have a lot of literal bulk, and it does bulge out toward the sea from Sal's vantage point, but the "raw" adjective can only be metaphorical. Reasonable readers may come to their own conclusions as to what "raw" may mean in this sentence. That combination of literal and metaphorical works to create an image in the reader's mind of the eagle's eye view Sal has as he looks over mountains, plains, and coasts. It's not likely Sal can see over the entirety of the continent, but his travels allow him to imagine the scope of the country.
The personified state of New York tosses a brown haze over the horizon that Sal imagines he can see. Sal contrasts this with California, and with a simile he calls California "white like washlines." It's not that lines used for drying clothes are generally white, but instead that white sheets and clothes are often hung up on clotheslines. Sal's pale imagery for California might be a reference to the fog there, and it might also reflect his feeling that there isn't anything on the West Coast for him—at least, not yet.
In Chapter 12 of Part 1, Sal describes his lover Teresa's body with similes, and he uses additional metaphorical language to characterize their time together.
In reverent and sweet little silence [Teresa] took all her clothes off and slipped her tiny body into the sheets with me. It was brown as grapes. I saw her poor belly where there was a Caesarian scar; her hips were so narrow she couldn't bear a child without getting gashed open. Her legs were like little sticks. [...] Then, two tired angels of some kind, hung-up forlornly in an LA shelf, having found the closest and most delicious thing in life together, we fell asleep and slept till late afternoon.
Sal uses a simile to describe Teresa's skin color as "brown as grapes." Normally we think of grapes as purple or white, but both varieties can appear brown. The simile suggests ripeness and sweetness, appropriate associations for a lover. Another simile compares Teresa's legs to "little sticks." Readers may disagree on what these consecutive natural similes suggest.
Sal metaphorically calls himself and Teresa "two tired angels" forgotten in Los Angeles (a city name which literally means "the angels") and figuratively shoved to the back of a shelf. These metaphors suggest that Sal and Teresa are good people, but they are worn out by their circumstances. Perhaps the thing that has tired them is their respective struggles with societal norms. After all, both of them are living outside of those norms: Teresa, for her part, is countercultural in the 1940s simply for her willingness to give birth outside of wedlock and sleep with a man she has just met.
In Chapter 4 of Part 2, Sal goes to a party thrown by a man named Rollo Greb, whom he describes with an allusion and metaphorical language.
[Greb] played Verdi operas and pantomimed them in his pajamas with a great rip down the back. He didn't give a damn about anything. He is a great scholar who goes reeling down the New York waterfront with original seventeenth-century musical manuscripts under his arm, shouting. He crawls like a big spider through the streets. His excitement blew out of his eyes in stabs of fiendish light. He rolled his neck in spastic ecstasy.
The allusion is to the operas of Giuseppe Verdi, a 19th century composer who, by Kerouac's time, would have been recognized as a great artist. By mentioning that Greb acts out Verdi's operas, Kerouac intends readers to understand that Greb is both cultured and eccentric: he doesn't just know these famous operas but loves them to the point of embarrassing himself in public in order to express his enthusiasm.
With a simile, Sal says that Greb "crawls like a big spider" in public, a brief but evocative image that allows the reader to imagine this eccentric, unkempt man slouching through Long Island. Sal metaphorically says that Greb's "excitement blew out of his eyes in stabs of fiendish light." Obviously this phrase cannot be literal, but the reader has no trouble understanding what it means: Greb's enthusiasm often seems brilliant and even violent.
In Chapter 8 of Part 2, Sal uses metaphorical language to describe how Marylou looks at Dean:
Marylou was watching Dean as she had watched him clear across the country and back, out of the corner of her eye—with a sullen, sad air, as though she wanted to cut off his head and hide it in her closet, an envious and rueful love of him so amazingly himself, all raging and sniffy and crazy-wayed, a smile of tender dotage but also sinister envy that frightened me about her, a love she knew would never bear fruit [...]
Readers already know by this point that Dean's relationships with women, including with Marylou, are fraught. Marylou, for her part, adores Dean violently and jealously. Sal uses a simile to compare Marylou's possessiveness over Dean to a desire to kill him and hide his decapitated head. The shocking simile is fitting—Marylou wants Dean to herself, kept in her home for all time. The reader might struggle to understand how this desire is anything like murder, but to Sal, who sees Dean's travels as a crucial part of him, Marylou might as well have killed Dean (or at least the Dean Sal knows) if she convinces him to settle down.
Sal also says that Marylou knows her love "will never bear fruit." It's fairly common, even in texts as old as the Bible, to metaphorically compare the product of something to fruit, since fruit is the product of a grown tree. The "fruit" that Marylou knows she'll never get from Dean might be his full attention or commitment.
Finally, note that Sal's description of Marylou's "dotage" also contains descriptions of Dean himself: Dean is "so amazingly himself, all raging and sniffy and crazy-wayed." Dean has this kind of hold on not only several women, but also Sal and Carlo. Does Sal also want something from Dean that Dean can't provide?
In Chapter 10 of Part 2, Sal is lonely and delirious with hunger. While roaming the streets, he has a transcendental experience that he describes with similes.
I realized that I had died and been reborn numberless times but just didn't remember especially because the transitions from life to death and back to life are so ghostly easy, a magical action for naught, like falling asleep and waking up again a million times [...] I realized it was only because of the stability of the intrinsic Mind that these ripples of birth and death took place, like the action of wind on a sheet of pure, serene, mirror-like water. I felt sweet, swinging bliss, like a big shot of heroin in the mainline vein [...]
Kerouac often characterized On the Road as a novel about a spiritual search for meaning, and he was insistent that his Catholicism drove this search. He would also, like Allen Ginsberg (Carlo Marx), learn about Buddhism, although Buddhist leaders didn't always think the two men got the belief system right. Regardless, this passage is an excellent example of the spirituality present in On the Road. Bodily deprivation has led Sal to a transcendent state, and it leads him to "realize" several things about the nature of his soul, including that it has been reborn "numberless times." With a simile, he compares the easy, forgettable process of reincarnation to "falling asleep and waking up."
He then speaks of the "intrinsic Mind," a unifying life force that he says powers the cycle of death and rebirth. This concept is far from original to him, but the Beats played a large part in introducing these ideas to the United States. The 1960s counterculture movement would also invest in the idea of a unifying life force, which writer Aldous Huxley called the "Mind at Large." To explain this concept to readers, Kerouac metaphorically says life and death are ripples across the intrinsic Mind, then expands on that with a simile: reincarnation is to the intrinsic Mind what wind is to a sheet of water. The ripples move across the surface, but they do not change any inherent properties of that surface.
Finally, Sal says he "felt sweet, swinging bliss," an alliterative and metaphorical description of his elevated mood. He expands on this with a simile that compares the sensation to "a big shot of heroin in the mainline vein." Kerouac tried, but was never addicted to, opioids like heroin, but many of his friends, including William Burroughs (Old Bull Lee) were lifetime users, and recreational opioid use is still associated with the Beat Movement.
In the second chapter of Part 3, Sal goes to Dean's house. Sal metaphorically describes himself as an angel, come to spirit Dean away on an adventure.
My arrival was somewhat like the coming of the strange most evil angel in the home of the snow-white fleece, as Dean and I began talking excitedly in the kitchen downstairs, which brought forth sobs from upstairs. [...] Camille knew what was going to happen. Apparently Dean had been quiet for a few months; now the angel had arrived and he was going mad again.
Sal uses a simile to compare his arrival into Dean's household to that of an "evil angel," which readers could interpret several ways. In the theology of some sects of Christianity, and perhaps most famously in John Milton's 1667 epic poem Paradise Lost, devils are angels who have chosen to rebel against God. Working from this framework, a reader might understand Sal as calling himself a demon here—and certainly he's sowing chaos into Camille's relatively comfortable and stable life with Dean.
Additionally, in the Bible angels are frequently harbingers of instructions from God that require humans to undertake difficult tasks or journeys. The parallels between that kind of angel and Sal in the above passage are obvious. In the same "evil angel" simile, Sal characterizes Dean and Camille's household as "the home of the snow-white fleece." Once again, this highly metaphorical description could be validly interpreted in a few ways, but the obvious reading is that Camille is an innocent bystander in this situation, "snow-white" and soft. Finally, Sal turns his earlier simile into a metaphor: "the angel had arrived," by which he means he himself has shown up on Dean's doorstep, and his presence spurs Dean into an insane need to travel.
In Chapter 4 of Part 3, Sal and Dean go to a jazz club. Kerouac's descriptions of jazz music are remarkably inventive, and this one is no exception. He uses similes and imagery to help the reader imagine the noise and energy of the crowd.
His tone was clear as a bell, high, pure, and blew straight in our faces from two feet away. Dean stood in front of him, oblivious to everything else in the world, with his head bowed, his hands socking in together, his whole body jumping on his heels and the sweat, always the sweat, pouring and splashing down his tormented collar to lie actually in a pool at his feet.
A simile compares the tone of the horn with a bell. Dean stands almost reverently as he listens, his body moving. In fact, Dean sweats so much that his collar is metaphorically "tormented"! Sal says Dean's sweat is "pouring and splashing"—readers would usually take this as metaphorical language, and that's not an incorrect way to read it here, but Sal's insistence that the sweat "actually" forms a "pool at his feet" casts some doubt on whether this deluge of sweat is metaphorical or literal. Once again, Kerouac's style mixes the figurative and the actual to heighten moments of altered consciousness and high energy.
A chapter later, Dean reflects on the jazz music the men heard the night before. Dean's dialogue is often obscure yet poetic, and isolating the specific literary devices that Kerouac employs here can be hard. But it's certain that metaphorical language and imagery are both a part of Dean's speech.
"Ah well"—Dean laughed—"now you're asking me impon-der-ables—ahem! Here's a guy and everybody's there, right? Up to him to put down what's on everybody's mind. He starts the first chorus, then lines up his ideas, people, yeah, yeah, but get it, and then he rises to his fate and has to blow equal to it. All of a sudden somewhere in the middle of the chorus he gets it—everybody looks up and knows; they listen; he picks it up and carries it.
There's a rhythm to Dean's speech in the same way that music has a rhythm, and his idiosyncratic dialogue is highly stylized, even when the ideas or claims are hard to follow. Dean claims that a jazz musician needs to "put down" (or express) "what's on everybody's mind." He metaphorically says that the musician must begin by "[lining] up his ideas"—perhaps introducing musical themes he'll return to—but then "rises to his fate and has to blow equal to it." This metaphorical language demonstrates how high-stakes Dean believes jazz can be. The musician metaphorically "picks it up and carries it." Dean seems to use "it" here in a colloquial sense, to refer to an unnamable essence or mood that the musician provokes with his ex tempore playing.
In Chapter 4 of Part 3, Sal and Dean go to a jazz club. Kerouac's descriptions of jazz music are remarkably inventive, and this one is no exception. He uses similes and imagery to help the reader imagine the noise and energy of the crowd.
His tone was clear as a bell, high, pure, and blew straight in our faces from two feet away. Dean stood in front of him, oblivious to everything else in the world, with his head bowed, his hands socking in together, his whole body jumping on his heels and the sweat, always the sweat, pouring and splashing down his tormented collar to lie actually in a pool at his feet.
A simile compares the tone of the horn with a bell. Dean stands almost reverently as he listens, his body moving. In fact, Dean sweats so much that his collar is metaphorically "tormented"! Sal says Dean's sweat is "pouring and splashing"—readers would usually take this as metaphorical language, and that's not an incorrect way to read it here, but Sal's insistence that the sweat "actually" forms a "pool at his feet" casts some doubt on whether this deluge of sweat is metaphorical or literal. Once again, Kerouac's style mixes the figurative and the actual to heighten moments of altered consciousness and high energy.
A chapter later, Dean reflects on the jazz music the men heard the night before. Dean's dialogue is often obscure yet poetic, and isolating the specific literary devices that Kerouac employs here can be hard. But it's certain that metaphorical language and imagery are both a part of Dean's speech.
"Ah well"—Dean laughed—"now you're asking me impon-der-ables—ahem! Here's a guy and everybody's there, right? Up to him to put down what's on everybody's mind. He starts the first chorus, then lines up his ideas, people, yeah, yeah, but get it, and then he rises to his fate and has to blow equal to it. All of a sudden somewhere in the middle of the chorus he gets it—everybody looks up and knows; they listen; he picks it up and carries it.
There's a rhythm to Dean's speech in the same way that music has a rhythm, and his idiosyncratic dialogue is highly stylized, even when the ideas or claims are hard to follow. Dean claims that a jazz musician needs to "put down" (or express) "what's on everybody's mind." He metaphorically says that the musician must begin by "[lining] up his ideas"—perhaps introducing musical themes he'll return to—but then "rises to his fate and has to blow equal to it." This metaphorical language demonstrates how high-stakes Dean believes jazz can be. The musician metaphorically "picks it up and carries it." Dean seems to use "it" here in a colloquial sense, to refer to an unnamable essence or mood that the musician provokes with his ex tempore playing.
In Chapter 8 of Part 3, Sal describes Dean's maniacal driving with two similes.
[The hitchhikers] were hardly seated, and I had hardly waved good-by to Denver, before [Dean] was off, the big motor thrumming with immense birdlike power. [...] It didn't seem like we were even going seventy but all the cars fell from us like dead flies on the straightaway highway leading up to Greeley.
Sal says that the motor of the car thrums, a verb that is nearly onomatopoeic, as it suggests the sound of an engine. The adjective "birdlike" is a simile, and it suggests the car has lightness and speed. It's not unusual for Kerouac to use natural metaphors and similes for mechanical or man-made objects in his prose, and Beat poet Allen Ginsberg often did this, too (for instance, in his poem "Sunflower Sutra"). Another natural simile follows: the other cars on the highway "fell from us like dead flies" because Dean is driving so aggressively. This helps the reader imagine Sal's perspective as he watches the road from the accelerating vehicle, and it also might remind the reader of how Sal and Dean's relationship works. For Sal, it seems that everything not connected to Dean is less alive, like the slow cars they leave behind.
Sal describes yet more of Dean's skilled but irresponsibly fast driving in Chapter 9 of Part 3. His description involves a simile, a metaphor, and precise verbs that allow the reader to imagine Dean's eager yet deliberate maneuvers.
Dean came up on lines of cars like the Angel of Terror. He almost rammed them along as he looked for an opening. He teased their bumpers, he eased and pushed and craned around to see the curve, then the huge car leaped to his touch and passed, and always by a hair we made it back to our side as other lines filed by in the opposite direction and I shuddered. I couldn't take it any more.
The Angel of Terror is the title of a 1922 mystery novel by Edgar Wallace, a prolific British writer whom Kerouac may well have read. Sal might be alluding to that book here, or possibly he's just using the phrase to suggest that the drivers whom Dean tailgates are terrified. After the "Angel of Terror" simile, Sal personifies the car as if it is a responsive horse or even an extension of Dean's body. The car "leaped to [Dean's] touch" in order to pass on the single-lane highway, a dangerous maneuver. Sal idiomatically says their car passed without getting into a wreck "by a hair," by which he means they barely made it.
In Chapter 11 of Part 3, Sal's descriptions of his travels become melancholy. This tone is communicated with a simile in which Sal compares himself to a traveling salesman who sells something no one wants to buy.
In the misty night we crossed Toledo and went onward across old Ohio. I realized I was beginning to cross and recross towns in America as though I were a traveling salesman—raggedy travelings, bad stock, rotten beans in the bottom of my bag of tricks, nobody buying.
First, note the alliteration in the phrase "old Ohio." After his usual brief descriptions of the places he crosses through, Sal reflects with some displeasure that he's only retreading the same ground as before. In a simile, he compares himself to a traveling salesman, and not a successful one: he says the kind of salesman he's similar to is "raggedy," with "bad stock" that won't sell. The "rotten beans" comment may be an allusion to the story of Jack and the Beanstalk, in which Jack buys magic beans that his mother thinks are a hoax. What is Sal selling, and why isn't anyone interested? Perhaps he worries in this passage that his attempts to find purpose and spiritual meaning are pointless "tricks" that are obviously rotten to everyone but him.
Dean, Sal, and Stan keep driving through Mexico. In Chapter 5 of Part 4, they reach Monterrey. Sal describes this leg of the journey with imagery and a simile.
We met nobody on this high road. It wound among the clouds and took us to the great plateau on top. Across this plateau the big manufacturing town of Monterrey sent smoke to the blue skies with their enormous Gulf clouds written across the bowl of day like fleece.
The "high road" is usually an English language metaphor to describe taking the morally superior path, but here Sal means it literally: their car is climbing up a slope to the top of a plateau, or the flat surface atop an elevated area. Sal describes their drive with imagery. This road goes up along a mountain that passes through clouds and mist, then takes the travelers into smoky Monterrey. An excellently descriptive simile compares the factories' smoke to fleece, which goes across the metaphorical "bowl of day" like writing. This sentence combines multiple literary devices that suggest different images, but a reader taking the entire sentence together might imagine the frosted and patterned glass of a decorative bowl, turned upside down to form the sky.