Orlando (Penguin Classics Deluxe Edition)

Originally written for Vita Sackville-West, Virginia Woolf's lover, Orlando is Woolf's strangest novel. Its protagonist starts out as a young man in love with Queen Elizabeth the First, lives to be an ambassador to Istanbul, becomes a woman later in life as she continues her life all the way to women's suffrage. Orlando is a manifold novel: a history of British literature, a satire on writers, a feminist novel, and a queer narrative. Unless you already have a Master's degree in British literature, it will be hard to map what in Orlando is an allusion to literary history and what is just a private in-joke. But contrary to popular belief, there is no such thing as fully understanding a novel, so if you liked Mrs Dalloway and To the Lighthouse, dive in.