1. If: The Untold Story of Kipling’s American Years by Christopher Benfey (Penguin Press)

In his elegant, engaging book, Benfey focuses on the decade that the Bombay-born, English-educated Rudyard Kipling lived in America, and particularly outside Brattleboro, Vermont, and became an American writer. In his nuanced and deep exploration into Kipling’s American decade, Benfey suggests that though Kipling has been regarded as the “jingoist Bard of Empire,” today’s time of rising nationalism and cultural antagonism is a perfect time to take a closer look at his gravitational pull in politics and culture. At a moment when Kipling’s poem “If” has been appropriated by everyone from Serena Williams to The Simpsons, much of his most creative work – including The Jungle Book and Captains Courageous – was rooted in his American experience, and Benfey brilliantly shows how it reverberates, shapes, and reflects American culture.

2. Four Friends: Promising Lives Cut Short by William D. Cohan (Flatiron)

Four of Cohan’s prep school classmates, all dead. In his wrenching lament of a book, the most famous of these young men was John F. Kennedy Jr., the heir to Camelot who perished two decades ago when his plane crashed off Martha’s Vineyard, but Cohan extends his inquiry to include three other Andover graduates who died violently – one in a mass shooting, other in a sailing accident, another struck by a taxi. In this powerful book, Cohan, a Vanity Fair journalist and the author of best-selling books such as The Last Tycoons: The Secret History of Lazard Frères & Co. and The Price of Silence: The Duke Lacrosse Scandal, the Power of the Elite, and the Corruption of Our Great Universities, raises profound, important questions about the demands of manhood and the pressures, expectations, and obligations of privilege.

3. The Code: Silicon Valley and the Remaking of America by Margaret O’Mara (Penguin Press)

In her wide-ranging, deep history of Silicon Valley, O’Mara gets behind the myth of geniuses in garages and uncovers the true origin story. O’Mara, a University of Washington history professor who worked in the Clinton White House, brings sophistication and nuance to her narrative, covering not only on the engineer-dominated culture of building products, but also the absence of attention to their implications for the world. O’Mara argues that massive government investment during and after World War II and the idea of “entrepreneurship and government” meant that, rather than being a sideshow in American history, the “new economy” of tech was intertwined with the old and that “old-line media and old-line politicians championed technology companies and turned their leaders into celebrities.”

4. The Last Book Party by Karen Dukess (Holt)

A late 1980s summer in the Cape Cod town of Truro is the setting for Dukess’s charming debut novel with a Gatsbyesque feel, in which a young, Jewish editorial assistant in Manhattan becomes a research assistant for a famous New Yorker writer with a sublime artistic wife and a handsome son, surrounded by an array of literati characters. With her pitch-perfect style, Dukess evokes the bygone gentility of the publishing world, and with references to the Walkman, the Rolodex, Laura Ashley, and Linda Ronstadt, conjures the days when the novel Bright Lights, Big City reflected the Zeitgeist. More than an entertaining novel of the era, The Last Book Party captures the dawning self-knowledge of an aspiring young writer who is held back by a mix of her insecurities, naivete, and expectations of the day who realizes that she has been intoxicated by illusions of brilliance but one day may be able to fulfill her own ambitions.

5. Maggie Brown & Others: Stories by Peter Orner (Little, Brown)

In literary shorthand, Orner has been likened to short story stars like Alice Munro and Raymond Carver, or to Philip Roth and Saul Bellow for his recurring characters. But with this collection of 44 stories and the novella “Walt Kaplan Is Broke,” Orner displays a capacious talent that should be recognized as uniquely his own. His feats of compression and scope, distilling a vast range of human emotion in a few sentences, are extraordinary and provocative and accentuated by his wit, including with story titles like “Speech at the Urinal, Drake Hotel, Chicago, December 1980.” At one point in an emotionally rich story, “Ineffectual Tribute to Len,” the cab-driving narrator suggests the limitations of novels and writes to his publisher in defense of stories. “You say stories don’t sell,” he begins, adding, “I’ve seen the numbers of my story collections and they aren’t pretty; I know I’m basically a charity case, but don’t you see? It’s what Chekhov teaches.” That is the influence Orner has metabolized and made his own.