We love gender-bending protagonists around here, and Orlando is the mother of them all. We talk Bloomsbury, whether Orlando is a self-insert of Virginia Woolf or her lover Vita Sackville-West (Or Lobelia Sackville-Bagins), a new Cumberbatch-esque name, and frankly the best fanfic idea we've had yet.
The web comic Oglaf (very NSFW)
Gentleman Jack on Netflix
Big Little Lies on HBO