Virginia Woolf's novel Orlando: A Biography was first released on October 11, 1928. Inspired by the tumultuous family history of the aristocratic poet and novelist Vita Sackville-West, Woolf's lover and close friend, it is arguably one of her most popular novels. Orlando is a history of English literature in satiric form. The book describes the adventures of a poet who changes sex from man to woman and lives for centuries, meeting the key figures of English literary history. Considered a feminist classic, the book has been extensively written about by scholars of women's writing and gender and transgender studies.

The novel has been adapted several times. In 1981, Ulrike Ottinger adapted it for her film Freak Orlando, with Magdalena Montezuma in the title role. In 1989, director Robert Wilson and writer Darryl Pinckney collaborated on a single-actor theatrical production.

Woolf was born into an affluent household in South Kensington, London, the seventh child of Julia Prinsep Jackson and Leslie Stephen in a blended family of eight that included the modernist painter Vanessa Bell. She was home-schooled in English classics and Victorian literature from a young age. From 1897 to 1901, she attended the Ladies' Department of King's College London, where she studied classics and history and came into contact with early reformers of women's higher education and the women's rights movement.