Jamaica Kincaid was born was born on May 25, 1949 at Holberton Hospital in St. John, Antigua. She was originally named Elaine Potter Richardson. Richardson was her mother's surname. Her parents were not married and her biological father never played a role in her life. Her mother, Annie, married her stepfather, David Drew, soon after Kincaid's birth. Kincaid considers Drew her father and he serves as the model for the fathers in each of her novels. Annie and David Drew had three subsequent children, all boys.

Jamaica Kincaid's mother taught her to read at the age of three. Kincaid won a scholarship to the Princess Margaret School and excelled as a student, despite her occasionally mischievous attitude. After her father fell ill, however, Kincaid, as the girl in the family, dropped out at the age of thirteen. She left Antigua at age seventeen and moved to Scarsdale, New York to work as an au pair. She stayed in Scarsdale for a few months, before moving to Manhattan to be an au pair for the family of Michael Arlen, a New Yorker writer. She remained with the Arlen family for four years. As she worked, Kincaid acquired her general equivalency diploma and started taking photography classes at the New School for Social Research. Eventually, she won a scholarship to Franconia College in New Hampshire, but dropped out after two years. After returning to New York in 1973, she changed her named to Jamaica Kincaid to be anonymous as she tried her hand at writing. Ingenue published her first article, "When I was Seventeen," in the same year. She soon became friends with Scott Trow, who wrote the "Talk of the Town" column in the New Yorker. Trow eventually introduced her to William Shawn, the magazine's editor. In 1976, Kincaid became a New Yorker staff writer herself. In 1979, she married William Shawn's son, the composer Allen Shawn. They had two children, Annie and Harold, in 1985 and 1988. They currently live in Bennington, Vermont where Shawn is a professor at Bennington College.

Kincaid's first book, At the Bottom of the River, is a collection of short stories that received the Morton Dauwen Zabel Award soon after its publication in 1983. Annie John was published two years later in 1985. The publication of Annie John was unique in that the New Yorker published each of the novel's chapters separately before they were compiled and published as the novel. For this reason, reviewers initially wondered if they should categorize the book as a novel or a collection of short stories. The independent nature of the chapters makes their compilation somewhat episodic, which is to say that each chapter involves a series of episodes about a certain time in a young girl's life. The strong voice of the narrator links the different segments together, but the book still differs from a tightly constructed novel in which every episode interlaces to form a close knit whole.

Annie John represents a classic bildungsroman or growing up novel, which chronicles the moral, psychological, and intellectual development of a character. More specifically, Annie John can also be recognized as a Caribbean bildungsroman. Many Caribbean bildungsromans not only focus on the central character's growth, but they also parallel their experiences with those of the West Indian colonies where they live. Other examples of similar Caribbean bildungsromans include Merle Hodge's Crick Crack, Monkey (1970), Zee Edgell's Beka Lamb (1982), and Michelle Cliff's Abeng (1984). In these novels, as in Annie John, the protagonist's growth toward maturity parallels her society's progress from colonialism to independence. In Annie John, the protagonist's conflict with the dominant mores of society can best be seen through her problematic relationship with her mother. The complexity of the narrator's emotions towards her mother demonstrates the often-difficult relationship between Antigua and its British protectorate.

Since the publication of Annie John, Kincaid has published six books: a group of prose sketches, Annie, Gwen, Lilly, Pam, and Tulip, in 1986; an essay on the politics of Antigua, A Small Place, in 1988; the novels, Lucy and The Autobiography of my Mother in 1990 and 1995; a memoir about her brother's death from AIDS, My Brother, in 1997; and My Garden Book in 1999. Major themes in Kincaid's word include the relationship between mothers and daughters, which is crucial in Annie John, the complexities of colonization, and gardening. Critics long have praised Kincaid's lyrical, incantatory prose, which is characterized by rich colorful details about life in the Caribbean, including names or local plants and foods. Her work has also been examined in light of post-colonial and feminist theories.