City Boy: The Adventures of Herbie Bookbinder

City Boy: The Adventures of Herbie Bookbinder is a 1948 novel by Herman Wouk first published by Simon & Schuster. The second novel written by Wouk, City Boy was largely ignored by the reading public until the success of The Caine Mutiny resurrected interest in Wouk's writing. Like The Caine Mutiny, the novel is semi-autobiographical in setting and situations, if not protagonist. In 1969, the novel was re-issued, with paperback editions in 1980 and 1992, and according to Wouk was translated into 11 languages. John P. Marquand, in a preface to the 1969 20th-anniversary release, likened Herbie Bookbinder to a city-dwelling Huckleberry Finn or Tom Sawyer.

In many of his novels Wouk evinces through his characters a love of Dickens, particularly in use of language to set mood. In City Boy he devises humorous twists of language to set a less-than-serious tone throughout this coming-of-age story. Also like Dickens, Wouk manages a large cast of characters, including more than a dozen adults (and a one-of-a-kind horse named Clever Sam) woven in-and-out of a narrative about children, with depictions that ring true both in description and actions.