Movies about transgender people don't number that many (at least in mainstream cinema), and even less so the further back you go, so ORLANDO is somewhat unique by virtue of its very existence. Based on a Virginia Woolf novel (which I haven't yet read, but definitely want to), it tells the story of Orlando, an English nobleman blessed/cursed with immortality and who changes sex from male to female. Without going into spoiler territory (e.g., when and why Orlando changes), the film is largely concerned with social roles and expectations of men and women, unfairness in how women have been treated, etc. I thought it was rather interesting to for Orlando to be possessive of a woman he fancies early in the film, only to be on the receiving end of a similar proposal later on as a woman. And then there was my favorite scene where Orlando sits in on a discussion between several famous writers/poets (including Alexander Pope). All of the feminist discussion and thematic content alone makes this worth a watch, but there are a few minor quibbles to be had. The chief one is due to the main character's immortality. You get several sections in different time periods that show Orlando's progress, but it gives the film an episodic feel at times. I also wasn't terribly satisfied with the way it ended, although I'd be at a loss to posit an alternate ending without extending the running time further (and I thought it was a good length already). Suffice it to say, this is one of the best performances I've ever seen out of Tilda Swinton, although she was less convincing as a man than a woman (for obvious reasons). Still, her character isn't the only fun the film has with gender fluidity, as Queen Elizabeth is played by Quentin Crisp and there are a couple castrati who provide some diegetic music. Aside from the performances, the production design, sets, costumes, and score were all equally good. For more open-minded viewers, I can wholeheartedly recommend this. It will definitely affect the way you think about gender/gender roles.