1. At the beginning of the novel, Sal Paradise admits to having ambivalent feelings about Dean, at first thinking him to be a little too tough, a real streetkid. Later, his feelings toward his friend change, though still mixed, as he calls him an "idiot" and an "imbecile," but also a "saint," and finally "the HOLY GOOF." Do you think Sal's opinion about Dean's character and intelligence is ever completely resolved? Why? Why not?
2. During Sal's first road trip west, he laments that "Boys and girls in America have such a sad time together." How does this observation, early in the novel, set the stage for the relationship between Sal Paradise and Terry, his Mexican girlfriend? Why doesn't he ever mention Terry's last name?
3. How does Dean Moriarty's obsession with sex and women compare to Sal's experience? Does Sal look upon his friend's "success" in bed with admiration, envy, or something else?
4. What part do women play in the core emotional relationship between Sal and Dean?
5. Though many of his poet and artist friends were gay, Kerouac, as revealed in his personal correspondence and journals, considered homosexuality to be a fault, a sin, a vice. In On the Road, Sal's friend Carlo Marx (based on Allen Ginsberg) is openly gay. What is the attitude of Sal Paradise toward gays and lesbians in Kerouac's novel? What is Dean's attitude?
6. At the end of every adventure with Dean, Paradise returns home to his aunt, in Paterson, New Jersey. Is Kerouac's novel a convincing demonstration that mainstream middle- and working-class values are inherently incompatible with the Beat lifestyle and philosophy of the road?
7. Whenever Sal and Dean have the chance to hear music, they choose jazz. What explains the dedication these characters have for this sophisticated African-American urban art form? What does Kerouac believe the jazz musician represents?
8. Almost every time that Paradise waxes poetic about heaven, God, and the road, shortly thereafter the topic of Death rears its head. How does Kerouac imagine the relationship between what Sal thinks of as heavenly bliss and the finality of death?
9. At one point on the road, Sal wonders, "for what's heaven? what's earth? All in the mind." What is heaven for Dean Moriarty and Sal Paradise? Do they share the same ideal, believe in the same kind of "heaven"?
10. Some critics have claimed that the world Kerouac depicts in On the Road glorifies the deeds of uneducated, criminal young men leading irresponsible lives, committing sacrilegious acts. Given today's low tolerance for youthful rebellion, particularly drug use, do you find the behavior of Dean Moriarty and Sal Paradise repugnant and totally inappropriate? Do you think Kerouac is approving or critical of his characters' behavior?
11. Why do you think On the Road, after more than forty years since its original publication, still maintains a magnetic hold on American youth culture? Is the novel's significance to your generation different from its significance to younger and to older generations? How has the meaning of On the Road changed for you since your first encounter with it?
Big Sur
0-14-016812-5
Book of Blues
0-14-058700-4
The Dharma Bums
0-14-004252-0
Jack Kerouac: Selected Letters 1940-1956
0-14-023444-6
Maggie Cassidy
0-14-017906-2
The Portable Jack Kerouac
0-14-017819-8
Some of the Dharma
0-14-028707-8
Tristessa
0-14-016811-7
Vanity of Duluoz
0-14-023639-2
Visions of Cody
0-14-017907-0
Visions of Gerard
0-14-014452-8
