On the Road | Discussion Questions 41 - 50

What is the main difference between Rickey's worldview and Dean's in On the Road?

Terry's brother, Rickey, is a lazy, uninspired worker who frequently puts off his responsibilities in order to relax and party. In this way Rickey and Dean are similar: both enjoy drinking and partying more than facing up to their daily responsibilities. The difference in their worldview is that when Rickey thinks about his responsibilities, he says over and over that things will be taken care of manana, or tomorrow. His gaze is set forward, looking ahead to when times will certainly be better. Dean, on the other hand, lives entirely in the present moment, rarely thinking about events to come or what his future holds.

In what ways does Dean "con," or cheat, Sal in On the Road?

Sal knows that Dean is a con man from the first moments after meeting him, but he forgives his friend's flaw by saying, "He was only conning because he wanted so much to live." The first time Dean outright cons Sal is after he makes the offensive joke about Sal's age. When Sal becomes upset, Dean pretends to cry, swearing he's never been so sorry before. Sal resists the emotional con initially, but eventually relents and forgives his friend. At the end of the novel after Dean abandons Sal in Mexico, Sal wonders whether their entire friendship was a con. He believed he was forming a deep bond with Dean, but perhaps the "rat" Dean was only taking what he needed—money and companionship—before moving on to his next victim.

What is the tone of On the Road?

Perhaps because Kerouac wrote the first draft of On the Road in just three weeks, the tone of his novel isn't consistent. He employs different tones at different times to elicit different responses. For example, while partying and traveling, the novel's tone is excited and energized, sometimes reflecting the characters' anticipation of upcoming adventures and sometimes reflecting their drug-and-alcohol-fueled consciousness. Other times, the novel's tone is reflective, such as when Sal contemplates his existence or relationship to nature. The overall tone, however, could be described as sad. Sal becomes wistful as he contemplates the fickleness of friendship. The women in the novel project sadness as they try to hold onto their men. Sal becomes disillusioned with his relationship with Dean, and at the end he realizes he has outgrown his companion's lifestyle. In the final paragraphs he watches as Dean "walked off alone" and Laura "began almost to cry."

How does death both contradict and complete the credo of the Beat Generation in On the Road?

Sal, Dean, and the other Beat characters are "tremendously excited with life." They had one credo—"life is holy and every moment is precious"—and so they live it fast, dangerously, and in the moment. They seemingly race across the land searching for every possible experience they can devour. But while this is going on, the Shrouded Traveler keeps reappearing to Sal. It is "pursuing all of us across the desert of life." Sal is mystified by this figure at first but finally realizes the figure "is only death." He considers that the one thing they are seeking in life is something pure and blissful that was "experienced in the womb and can only be reproduced ... in death." When he discusses his theory with Dean, Dean quickly agrees with Sal's analysis, but he simultaneously refuses to accept it as a goal because, as Sal acknowledges, "we're all of us never in life again." So death is to be avoided at all costs by the Beats, but it will also prove to be the ultimate goal, the only place where their cravings can be fully satisfied.

Which is more valuable in On the Road, a traditional education or a street one?

For the Beat Generation, having a street education, like Dean's, is valuable for living life on the road. Dean knows a lot about conning his way from coast to coast, stealing what he needs to survive and sneaking out of tricky situations. However, most of the Beats are snooty about their educations and exclusive about who can join their intellectual parties; many don't want to accept Dean into their group. At the end of the novel, Sal reestablishes his friendship with prep-school friend Remi, and they no longer have space in their lives for Dean, the ultimate outsider. So while the Beat lifestyle values streetwise education, the novel as a whole values traditional education.

What role do visions and hallucinations play in On the Road?

Through the use of drugs and alcohol, many characters seek heightened realities, including hallucinations and visions, in the hope of gaining a deeper understanding of their existence. In the Beat lifestyle, "madness" like Dean and Old Bull Lee possess, is highly prized. When Sal experiences hallucinations through starvation and drug use, however, he doesn't enjoy the experience. Similarly, when Dean has vivid visions of Marylou he violently attacks and threatens to kill her. Many visions reoccur in the novel, suggesting symbolic depth. Ed Dunkel, for example, regularly has visions of ghosts—sometimes he is the ghost and sometimes other ghosts visit him. These visions are viewed as wisdom about time and the interconnectedness of human souls, while Sal's visions of the white horse symbolize his connection to nature.

Does Sal ever truly love anyone in On the Road?

Whenever Sal meets a new woman, he claims to be in love with her: Rita, Terry, the young black prostitute, the "Mexican midget." For Sal, it seems that love and lust are synonymous. When he "loves" women he actually just wants to sleep with them. Even Terry, whom he pretends to build a family with, is abandoned without a second thought as soon as things get difficult. The only person Sal remains dedicated to, although he never claims to love him, is Dean. Unlike any woman in Sal's life, Dean is given loyalty, understanding, forgiveness, and fidelity. Regardless of Dean's sins and the many other friends who cut ties with him, Sal remains Dean's faithful companion.

What does Dean's childhood reveal about his character in On the Road?

Dean's childhood was traumatic and transient. He was raised by an alcoholic father who traveled from city to city as a bum, taking young Dean along with him. Dean's father always put himself first—Dean spent his childhood in bars rather than in schools—and couldn't face the responsibilities of raising a child. When he made money selling homemade flyswatters, for example, he drank the profits rather than putting them toward a more comfortable existence for his son. Then one day Dean's father vanished. Despite his rough upbringing, Dean desperately wants to find his father and spends much of the novel searching for him. As a father himself, Dean mirrors his dad's poor decisions. He travels from city to city chasing momentary happiness, often at the bottom of a bottle, and selfishly abandons his children while living on the road.

Why might Kerouac have had a difficult time selling On the Road when he first wrote it?

On the Road was written in the 1950s, which was an era of specific and strict social expectations. During this time most people planned ordinary, mainstream lives, and if they experienced disillusionment or unhappiness, they hid those feelings from the outside world. On the Road was considered provocative and even outrageous, not only for its descriptions of wild sex and drug abuse but also because it encouraged wanderlust and a rebellion against the staid and ordinary lives of Main Street. The novel criticizes the social order as being "square" and encourages young readers to value their personal experiences and happiness over the standards of their communities.

How does On the Road treat the balance of good and bad forces in the world?

Sal starts out in the novel as an idealized youth who wants to live a clear-cut, free existence chasing honesty and purity by living in the moment. Everything that is "good" in his mind is equally honest and free: jazz, sex, the open road, and Dean. Everything that is bad, on the other hand, is restrictive: police officers, social expectations, and family life. As he matures, however, he begins to see that nothing in life is truly clear cut: the good is always mixed with the bad and moments of pure clarity are rare. This is best exemplified in his relationship with Dean, who has many good qualities but who is also violent, selfish, and sometimes dangerous.