On the Road | Discussion Questions 1 - 10

What draws Dean and Sal together when they first meet in Part 1, Chapter 1 of On the Road?

When Dean and Sal first meet, they each want something the other possesses. Dean, who grew up impoverished with an alcoholic father, wants to become an intellectual. He doesn't have the money or desire to obtain a traditional education, so he befriends intellectuals like Sal with the hope of learning through osmosis. Sal, who was raised with a more traditional upbringing, wants to experience the freedom of youth and live a life without thinking about the consequences, but he doesn't quite know how to achieve this state of being. When Sal and Dean meet, they see how they can help each other, which creates the framework for a passionate and long-lasting friendship.

How does Sal's character change during his first trip across America in On the Road?

When Sal first sets off on his journey across America, he believes the destination is more important than the journey. He has a strict plan of how he would like to travel from New York to Denver and quickly becomes disillusioned when the first part of his journey doesn't develop as he expected. He romanticizes everything, from the locations to his fellow travelers to the lessons he'll learn along the way. During the second part of his journey, from Denver to San Francisco, Sal learns to appreciate the random experiences hitchhiking provides, and he forms his first "on the road" relationship with Terry. He begins to embrace the Beat mentality of living life without concern for the consequences and serving one's personal desires first.

How does Sal's perception of his friends change by the time he arrives in Denver in Part 1, Chapter 6 of On the Road?

Until Sal reaches Denver, his experience of the Beat Generation does not require adapting himself to his friends' social expectations. When he arrives in Denver, however, Sal sees that his friends have splintered into two groups: those from solid families who are reasonably well-off and those from more troubled, less prosperous families. Those from the troubled background, Dean and Carlo, embrace living life without consequences, heightening their realities through drugs, alcohol, and sex. They enter each experience thinking only of what they can gain from it, not what they can offer. As soon as they have taken what they want to elevate their experiences, regardless of the consequences, they move on. For members of the Beat movement, which Sal is just beginning to join at this point in the story, the road stretches only forward, never back.

How does On the Road reflect the American experience?

On the Road portrays all aspects of the American experience—both positive and negative—in a romanticized light. Migrant workers are portrayed as being happy, enjoying their impoverished position in life. All the hitchhikers, "bums," and homeless people are happy, generous, and chasing adventure. Races live together harmoniously, as in Mill City and the various jazz bars across the country. Everyone, from farm boys to college students to well-off families, are happy to pick up hitchhikers on the side of the road and help them along their journey. People like Remi sleep with their houses unlocked, and young men like Sal survive for weeks eating nothing but slices of all-American apple pie. The America presented in the novel is romanticized as picturesque and positive.

In what ways is Dean Moriarty both a hero and a villain in On the Road?

Dean Moriarty is the hero of the counterculture movement in On the Road. More than any other character, Dean embodies the Beat experience of living life without consequences. For Dean the road is always moving forward. There are always new women to love, new cities to visit, new adventures to chase. His exuberance for life attracts young intellectuals (like Sal) like a moth to the flame. Everyone wants to be like Dean and live life with his passion. To those in the wake of Dean's passion, however, particularly the women in his life, Dean is a villain. He makes promises. only to break them. He cheats on his wives and abandons his children. He steals cars, food, and gasoline without a second thought, taking whatever he can from the world and not caring what the consequences of his actions might be.

How does being fatherless affect the characters in On the Road?

In On the Road, many of the characters are fatherless: Dean's father abandoned him as a child, Sal's father died, and Stan's father is out of the picture. Each of the novel's main characters is searching for something, some definition of their existence, that is missing from their lives, just as their fathers are. Without proper modeling, both Sal and Dean shirk their fatherly responsibilities: Dean to his own children; and Sal to little Johnny, Terry's son. Dean spends much of his time on the road searching for his missing father, and in a way, so does Sal. During his first journey, Sal was deeply moved by the relationship between Mississippi Gene and the young boy he protected on the road. Sal desires that sense of belonging and protection from Dean. When Dean is incapable of providing it, Sal eventually learns to provide it for himself.

Why are Dean and Sal interested in young girls in On the Road?

During their adventures on the road, Sal and Dean have romantic dalliances with a variety of women. Whenever they are at a party or brothel, both men gravitate toward young women, with both men bedding girls as young as 14. Dean's motives seem particularly predatory as he voices attraction to children, like Old Bull Lee's eight-year-old daughter, Dodie Lee. While these attractions belie a dark element of a subversive or counterculture life, they also have symbolic meaning. While on the road, Sal travels to escape the "social death" of a traditional life. In fleeing death, he embraces youth. For this reason he would rather sleep with young, hopeful girls than older, life-hardened women.

What does the Shrouded Traveler, mentioned in Part 2, Chapter 4, and Part 4, Chapter 2, represent in On the Road?

Sal often dreams of a Shrouded Traveler. At first, the Shrouded Traveler symbolizes death—the death of one's soul when adhering to traditional cultural values such as getting married and having children. In order to escape that death, Sal and his friends embrace the Beat life, including drugs, sex, and parties that elevate their existence beyond consequence and responsibility. Whenever the Shrouded Traveler appears, it is motivation for Sal to keep pressing forward. At the end of the novel, however, Sal thinks the Shrouded Traveler might actually be Dean. In the final chapters, Sal has settled into a traditional relationship in New York and seems fulfilled. Dean, however, is alone and lonely. He has experienced social "death," and there is no longer satisfaction in life on the road.

What is significant about the narrative style in On the Road?

Although written in the past tense, Kerouac's style creates a sense of the present moment. The style is created in two ways. First, it is written as a journal, so everything that happens is told in the past tense. However, Kerouac uses stream-of-consciousness narration, giving readers the sense that events are unfolding in the moment. The style reflects, in many ways, the jazz that Sal and Dean keep searching out. Jazz is improvisational, and Kerouac's style picks up on this method so effectively that it suggests it is formed in the moment and never revised. The truth, of course, is that Kerouac revised On the Road carefully and repeatedly.

How does On the Road depict different races?

On the Road depicts certain characters as caricatures or stereotypes rather than as realistic representations of individuals. African Americans, for example, are all boozy jazz players who speak in jazz slang and drink heavily. Mexican men (like Rickey and Ponzo) are lazy layabouts who concoct quick moneymaking schemes but are too drunk to carry them out. Marginalized migrant workers are content in their role, which the narration romanticizes. Sal, and arguably Kerouac himself, romanticize the plight of minorities during a racist time in American history. Sal wishes he belonged to black and Mexican cultures because he thinks they would give him a sense of belonging.