4. Lady Orlando – Orlando, A Biography
Being a little mad certainly has its perks. It’s probably how, in the year of 1928, Virginia Woolf managed to publish Orlando, A Biography, which is a fictional work telling the life of one young man who decides to live forever. Determined to break boundaries set forth in fiction of the day, Woolf titled her book about a transgender person as a “Biography,” hoping to create a new type of “trans-genre” written work. Perhaps an even more interesting fact about Orlando, A Biography is that the novel is traditionally held to be written as an immense love letter written for and about Woolf’s lesbian lover, Vita Sackville-West.
Orlando starts out as a young Elizabethan knight determined to never grow old. He maintains this attitude well throughout a series of love affairs and other adventures, until Orlando is exposed to particularly violent riots which shake him to his core. At this point, he falls into a deep slumber from which he cannot be roused. Upon his eventual awakening, Orlando is surprised to discover that he has transformed into a woman. Everything about Orlando remains the exact same, save for the fact that he now has the body of a woman.
At first confused and dismayed by the transformation, the now Lady Orlando wanders for a spell, trying to get bearings on her new life. It isn’t until an incident happens where (at the briefest flash of her bare ankle) someone on a ship almost falls overboard to their death that she realizes just how much power she actually holds as a woman and starts to love her new body. Deciding not to be held down by conventions anymore, Lady Orlando spends a long period of time switching back and forth between male and female roles, changing her lifestyle and dressing customs as she sees fit.
Lady Orlando, for being conceived in 1928, shows us a surprisingly provocative attitude that many modernists would still have trouble adjusting to. Gender roles are greatly debated in today’s society still and although concepts of gender and sexuality are starting to become a little more fluid, there is still a long way to go before we can escape the notion of labels. Although her story is over 80 years old, she presents us with a perspective that many of us should still learn from today, which is why Lady Orlando ranks in at the Number 4 slot.
Tags: Adventure, books, fairy tale, fantasy, gay character, gay fantasy, gay-nerds, lady orlando, lesbian character, lesbian lover, lesbian nerds, LGBT fiction, literature, love, orlando, pushing boundaries, romance, Top 10, Transgender, transgender character, virginia woolf, vita sackville west