City Boy: The Adventures of Herbie Bookbinder

Set in the spring and summer of 1928, City Boy spins the tale of an 11-year-old Jewish boy from the Bronx, New York City, New York. The novel first follows Herbert Bookbinder through the final days of school at New York Public School 50, and then through a summer spent at Camp Manitou, a summer camp in the Berkshire Mountains operated by his school's principal. Herbie's city world is one of endless daydreams and small urban pleasures: playing in empty lots, going to the movies on Saturday, arguing with friends around a forbidden campfire, feasting on "fraps" (in this context, a fancy sundae) in Mr. Borowsky's candy store, and going out to dinner at Golden's Restaurant with his dad and his dad's business partners.

Herbie is an exceptionally bright but fat little boy, a seventh grader and a star pupil. Although a poor athlete, Herbie yearns to be a "regular guy" among his schoolboy peers and constantly struggles against the consequences of his own quick wit and natural clumsiness with his rival, Lennie Krieger, the son of the business partner of Herbie's father, Jacob Bookbinder. Both blessed and cursed with a highly-active imagination, Herbie is also on the verge of adolescence, and the story revolves around his continuing quest to win the heart of the fickle, red-haired Lucille Glass.

Herbie, his parents, and his thirteen-year-old sister, Felicia, dwell in an aging Homer Avenue apartment house. Jacob Bookbinder is founder and part owner of an industrial ice-making plant, known to Herbie and his cousin Cliff Block as The Place, a location that plays both a significant role in Herbie's fate and an adult sub-plot that frames the climax of the story.

Herbie contrives to have himself (and his sister, his cousin Cliff Block, and his rival Lennie) sent to Camp Manitou (run by Mr. Gauss, the principal of P.S. 50, as a source of summer income) when he learns that Lucille Glass will be there. The second half of the novel skewers the summer camp scene of the 1920s even as it sets up a succession of abject failures and spectacular successes for Herbie.

Herbie and Cliff contrive to burglarize The Place to finance a well-intended camp project, and that crime is the device by which all the subplots come together in Dickensian fashion, at a cost to Herbie's bottom if not his psyche. Wouk fashions a moral to the tale without preaching, but the boy's victory in the quest for Lucille proves tenuous at best.

"The small stout boy reviewed several incidents of the day in his mind: concrete against his nose, jeers at his black felt beard, 'General Garbage,' and the recent threat to render his face concave."

"It has gone down among the teachers of P.S.50 as one of the great unsolved crimes of pupil cunning. Strange! Teachers set themselves up to be wondrous wise—yet to this day it has not occurred to one of them that 'outfielder' is a dactyl."

"Like a sailor embarked in a hell ship, like a policeman assigned to a tunnel, like a priest sent to a squalid settlement in the fever belt of India, Herbie Bookbinder was committed beyond hope of release to a summer in Bunk Thirteen."

"After a short silence, conversation was resumed on other topics. Herbie was noticeably shouldered out of the talk. He had committed that breach of manners, unforgivable among adults as well as among boys: he had known more than the leader."

"Nobody, least of all Herbie, overlooked the significance of his given name repeated twice by the captain. It fell sweetly on the fat boy's ears. The speaking of a name can be the conferring of an award above gold medals. Herbie missed the fireworks, but he never regretted them. From that day he was 'Herbie' to all the boys in his bunk except Lennie. Outside the bunk, however, Herbie's designation was fixed. First impressions are hard to change. He had been publicly pilloried on the train as General Garbage, and General Garbage he remained all summer. And if at the age of seventy he should run into a seventy-one year old gaffer formerly of Bunk Thirteen, he should be remembered, if at all, as General Garbage."

"A lonesome, quiet situation, you might say, yet he had plenty of company. Misery sat at the fat boy's right hand, and Shame at the left; and they made the morning mighty lively for Herbie between them."

The film rights to City Boy were purchased by Columbia Pictures "for a small payment"[2] under the working title The Romantic Age. It became the 1951 film Her First Romance, with the character of Herbie Bookbinder changed into a non-Jewish teenaged girl played by Margaret O'Brien (with a brother named "Herbie"), but the plot elements largely remained the same.[3]

There has been some confusion regarding the title of the book, as can be seen in the variations used within this Wikipedia page. The first edition of the book had the title listed as "The City Boy" on the title page, with the subtitle: "The Adventures of Herbie Bookbinder and His Cousin, Cliff". When the twentieth anniversary edition was issued (which in fact was issued 21 years after the original publication date), the title was shortened to "City Boy: The Adventures of Herbie Bookbinder". The first edition of "The Caine Mutiny" used "City Boy" on the back flap of the dust jacket, but "The City Boy" on the back panel of the dust jacket. The back panel was shortened to "City Boy" in subsequent printings. [4]