On the Road | Study Guide

Jack Kerouac

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On the Road | Discussion Questions 21 - 30


Why does Sal call Dean his "brother" in Part 3, Chapter 7 in On the Road?

Sal and Dean forge a deep friendship that Sal hopes will last a lifetime. They travel across the country together, escaping scrapes with the law, meeting a variety of interesting people, even sharing lovers. They become so close, Sal refers to Dean as his brother. This label signifies the deep bond Sal feels with Dean, but it is also used to "vouch" for Dean, particularly during bouts of bad behavior. Sal first calls Dean his brother while they are staying at Frankie's place when neighbors confront Dean for trying to seduce a young girl. Later, Sal again claims Dean as his brother after Dean loses control of the Cadillac and gets it stuck in the mud. Sal tries to convince others, and perhaps even himself, that Dean can be trusted.

What is the significance of Dean's injury in Part 3, Chapter 2 of On the Road?

Dean suffers an injury to his hand during a fight with Marylou before setting out on the third journey with Sal. During a vicious fight in which Dean threatens to kill Marylou after smoking bad "tea," he hits her, breaking his thumb. This event highlights the darker, violent side of Dean's character, which becomes more apparent as he descends into drug and alcohol abuse. The attack after a "bad trip" also highlights Dean's loosening hold on reality. He quickly bandages the wound, much like he slaps bandages on the emotional wounds of his women, but he doesn't pay attention as the wound festers and worsens. Throughout the trip, Sal describes the bandage as filthy and unraveling, much like Dean's grip on reality.

How does Sal's view of women change over the course of On the Road?

When Sal first meets Dean, he longs to embody the cool charisma Dean uses to bed multiple women, never caring about the consequences of those relationships or the way women feel in return. In the beginning, Sal cares too much and is desperate to impress his sexual partners, although he often fails. Outside of the bedroom, Sal (like most men in the 1950s) view women as subordinate to men, accessories rather than partners. His views of women like Marylou and Camille, who distract Dean from his friendship with Sal, is single-mindedly negative. Halfway through the novel, Sal begins to recognize and even appreciate the strength of women like Galatea and Frankie. By the end of the novel, he has settled into a monogamous relationship with Laura, a woman he seems to view as his equal.

How does jazz reinforce the themes of On the Road?

Jazz is Sal and Dean's favorite music, and they travel across the country visiting various jazz bars to hear their favorite musicians "blow." Jazz musicians embody a musical freedom similar to the freedom Sal and Dean chase on the road. The style celebrates individual creativity and improvisation, with numbers filled with unexpected twists and turns that sound adventurous. The music, which elevates reality like a drug, becomes spiritual, especially for Dean who views jazz players as gods. When Dean catches sight of George Shearing, he comments, "Sal, God has arrived." The music also gives Sal and Dean access to African American culture, which they romanticize even though they never consider the struggles of the marginalized community and how they use art for self-expression.

What is the IT that Sal and Dean chase in On the Road?

Although never clearly defined, IT appears to be the meaning of life, which can only be experienced when one is completely living in the moment, not pandering to social conventions or others' expectations. Dean sees IT in the eyes of jazz musicians in the midst of a great riff, and in older members of the Beat Generation, like Bull Lee, who have reached enlightenment. Wherever they travel, Sal and Dean search for IT, hoping to uncover a pure reality in each city they visit. The closest they come is in Mexico, where people seem to live without the influence of outside forces, embracing their culture and societal place peacefully.

In what ways is Dean a good or bad friend in On the Road?

Although Dean can always be counted on to join a journey or adventure, his motivations for traveling cross country are always selfish—he's searching for his next high, his next sexual partner, his next adventure, or his father. He cares very little about the emotional needs or wishes of those around him. This attitude begins alienating friends quickly, first those in his group of friends in Denver, then in San Francisco, and finally in New York. Despite Galatea's warnings that Dean would abandon him, Sal believes Dean values him. When Dean does abandon Sal in Mexico when he is sick, Sal calls him a "rat." At the end of the novel, no one, including Sal, has space for him in their lives.

Why does Kerouac rely so heavily on the use of secondary characters in On the Road?

The main characters of On the Road are Sal and Dean. The rest of the characters move in and out of the story but rarely affect the novel's main action or story line. Still, it is partly these secondary characters that make On the Road so interesting. Although Kerouac only provides snapshot descriptions of characters such as Mississippi Gene, Henry Glass, Beverly the waitress, and countless others, they seem like real people. Together, this group of acquaintances embodies America and lends a realistic humanity to the fast-paced story. The details of their characters also lend believability to the narrative as Sal and Dean interact with them during the novel.

How does Old Bull Lee's lifestyle embody the Beat movement in On the Road?

Bull Lee is the quintessential Beat teacher and is viewed as a mentor by younger members of the Beat movement like Sal and Dean. He lives in New Orleans on a homestead with his wife and children. Secluded from the rest of society, Bull Lee is free to use drugs and create wacky inventions, truly living in his creativity and outside the social expectations for a man his age. Additionally, he has traveled across the country and around the world, meeting interesting people and experiencing exhilarating events. Bull Lee lives almost entirely in the moment, focused solely on his own pursuits, and nothing, not even the responsibility for raising a family, distracts him from his pursuit of heightened reality.

In what ways is Sal and Terry's relationship doomed in On the Road?

Sal and Terry spend only a few short weeks together in On the Road. During that time, Sal enjoys "playing house" with her and her son, even claiming to love them as a husband and father would. The relationship, however, is entirely fantasy based. Terry is still married and claims her family would never approve of her dating a white man. She and Sal come from completely different backgrounds: she is a poor migrant worker while he is an educated middle-class man. Sal embraces the migrant lifestyle for a while, but merely as entertainment. As soon as things get uncomfortable when the weather changes, he quickly escapes back to a life of comfort in New York. While Sal has the financial freedom to come and go as he pleases, Terry is unable to escape her impoverished life.

How does On the Road portray the passage of time, and how does it affect the novel's main characters?

Time is a transient force in On the Road, one that cannot be stopped, contained, or controlled. Because time marches steadily forward, Sal and Dean desire to live fully in the moment without considering what came before or what will come after. As a result, they struggle to maintain relationships with anyone who lives outside the present moment. This side effect is of little consequence to Dean. Whenever he attempts to reflect on his past with his cousin and father, he ends up hurt. Sal, on the other hand, struggles with the complications of living life without reflection. The novel itself, written in the past tense, is Sal's attempt to process the events of his past that were simply experienced in the moment. Looking back, he hopes to uncover a deeper meaning.

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