If you like Catcher in the Rye by J.D. Salinger
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Catcher in the Rye by J.D. Salinger: "The story of three days and nights spent in New York City by Holden Caulfield, a sensitive, intelligent 16-year-old, who confronts the 'phony' values of the adult world." (Book summary).
If you enjoyed this book's setting and themes of mid-late 20th century exploration of counterculture and rejection of the mainstream societal values of the time, here are some other titles you may enjoy:
Catch-22 by Joseph Heller
Set in Italy during World War II, this is the story of the incomparable, malingering bombardier, Yossarian, a hero who is furious because thousands of people he has never met are trying to kill him. But his real problem is not the enemy—it is his own army, which keeps increasing the number of missions the men must fly to complete their service. Yet if Yossarian makes any attempt to excuse himself from the perilous missions he’s assigned, he’ll be in violation of Catch-22, a hilariously sinister bureaucratic rule: a man is considered insane if he willingly continues to fly dangerous combat missions, but if he makes a formal request to be removed from duty, he is proven sane and therefore ineligible to be relieved. (amazon.com)
Fight Club by Chuck Palahniuk
The story of a young man who discovers that his rage at living in a world filled with failure and lies cannot be pacified by an empty consumer culture. Relief for him and his disenfranchised peers comes in the form of secret after-hours boxing matches held in the basements of bars. (worldcat.org)
Less Than Zero by Bret Easton Ellis
Clay comes home for Christmas vacation from his Eastern college and re-enters a landscape of limitless privilege and absolute moral entropy, where everyone drives Porches, dines at Spago, and snorts mountains of cocaine. He tries to renew feelings for his girlfriend, Blair, and for his best friend from high school, Julian, who is careering into hustling and heroin. Clay's holiday turns into a dizzying spiral of desperation that takes him through the relentless parties in glitzy mansions, seedy bars, and underground rock clubs and also into the seamy world of L.A. after dark. (amazon.com)
Naked Lunch: the Restored Text by William S. Burroughs
Bill Lee, an addict and hustler, travels to Mexico and then Tangier in order to find easy access to drugs, and ends up in the Interzone, a bizarre fantasy world, in a commemorative edition that features restored text, archival material, Burroughs's own later introduction to the book, and his essay on psychoactive drugs. (worldcat.org)
On the Road by Jack Kerouac
Follows the counterculture escapades of members of the Beat generation as they seek pleasure and meaning while traveling coast to coast. As he travels across 1950s America, aspiring writer Sal Paradise chronicles his escapades with the charismatic Dean Moriarty. Sal admires Dean's passion for experiencing as much as possible of life and his wild flights of poetic fancy. (worldcat.org)
The Outsiders by S.E. Hinton
The struggle of three brothers to stay together after their parent's death and their quest for identity among the conflicting values of their adolescent society. (catalog description)
Slaughterhouse-Five by Kurt Vonnegut
Centering on the infamous firebombing of Dresden, Billy Pilgrim’s odyssey through time reflects the mythic journey of our own fractured lives as we search for meaning in what we fear most. (amazon.com)
In addition to the novels listed above, you may be interested in the following film:
Rebel Without a Cause by Nicholas Ray
Jim Stark, the teenage son of a well-to-do family, is overcome by loneliness, frustration and anger, which leads to violence when he seeks approval of a gang of high-school hoodlums.