Orlando

Because even its subtitle is subversive. Written as a valentine to Woolf’s lesbian lover, the book is anything but a biography. It is a gender-bending, time-traveling work of fiction that stretches from Elizabethan England to modern times—with the central character never aging, but changing sex. The book explores the fluidity of gender while poking fun at the pageantry and conventions of aristocratic English life, as well as taking to task the English tradition of male primogeniture. Fans of the book must also watch director Sally Potter’s brilliant film adaptation, Orlando, that stars a young, transcendent Tilda Swinton. 

Though I am committing one of the greatest spoiler crimes in book-herstory by including Orlando on this list, how could I not?

I always remember the line towards the end, when Orlando is standing in a department store: "Someone lights a pink candle and I see a girl in Russian trousers." It alludes to her (and our) memory of the earlier glorious Thames frost scene, where Orlando first falls in love with Russian Princess Sasha. Like Orlando, we all walk among the ghosts of London's history, and our own history, and a single trigger can catapult us into… show more.

This short novel was groundbreaking when first published in 1928 and is still unsurpassed. At the time, it was illegal in the UK to publish a story about a lesbian relationship, unless presented as a fantasy. Inspired by Woolf’s real-life relationship with Vita Sackville-West, the central character Orlando gallops through the centuries from Elizabethan England to 17th century Constantinople and beyond, shifting gender and enjoying a variety of male and female lovers as they go. The novel taught me a lot about the power and pleasure of writing otherworldly elements into what is seemingly a ‘real’ world.

This brilliant novel is the wildly imagined “biographical” tale of Orlando—a poet who lived for centuries (1588-1928), first as a man and then as a woman—was far ahead of its time in so many ways. This fantastical story serves as a treatise on gender and sexuality, a meditation on the nonbinary, a century before the gender revolution we live in today. And yet, at its heart, Orlando is truly a love poem to the nonbinary human (Vita Sackville-West) who stole Virginia Woolf’s heart. 

I have included this book for all readers who love a huge narrative arc, in this case, a life that stretches over centuries and changes gender. It was an early influence on me and taught me that fantasy can be powerfully embedded in a plausible historical reality and can be just as powerful and emotionally transforming as a factual biography. Woolf was also a hundred years ahead in terms of nuanced gender and throws out all societal restraints of conventional femineity in her depiction of Orlando, the original his/her hero/ine.