Sag Harbor

Set in 1985, the story follows Benji Cooper, one of the few Black students at a private high school in Manhattan. Through the school year he endures roller-disco bar mitzvahs, long sessions of Dungeons & Dragons, and late-night cable TV. An early blunder on his first day of high school, tied to his love of the horror magazine Fangoria, marks him for the rest of his time there.

Every summer Benji leaves the city for Sag Harbor on Long Island's East End, where a close-knit community of Black professionals has created its own world. With the parents driving out only on weekends, Benji and his friends have the run of the place for three months. He is as puzzled by this all-Black enclave as he is by the white world he moves through during the rest of the year, yet he hopes this season might bring change.

The summer brings plenty of obstacles: secret handshakes he has to learn, a fresh vocabulary of insults to master, a stubborn haircut, the New Coke fiasco of 1985, and a private weakness for Lite FM. Each challenge tests his efforts to remake himself.

The novel is a humorous, affectionate coming-of-age story that uses the embarrassments of adolescence and the urge to reinvent oneself to examine how identity takes shape, both for an individual and for a community. Whitehead drew on his own summers in Sag Harbor, and the book is often read as semi-autobiographical. It was published in 2009.