The film takes an “I am Spartacus” approach to the text, casting an assortment of trans and nonbinary performers as a gallery of incarnations of Orlando or as people who give their first name as Orlando (including Oscar S Miller and Janis Sahraoui), plus one who plays the actual Woolf character. Then it puts them in dramatic or comedic sketches (and in some cases, tableaus that feel almost like art installations, sometimes with visible lighting rigs) and lets them muse on the process of transitioning and the obstacles placed in the paths of individuals trying to do it. 

One sequence shows a group of Orlandos waiting in a doctor’s office who can prescribe hormones. Back in the doctor’s office, one of the Orlandos is asked intrusive and leading questions about their feelings about their genitalia, and a subsequent conversation between Orlandos reveals that one has to lie to the doctor and say that you hate your genitals to get the prescription—one of many examples of how people’s right to determine their own identity and presentation is held hostage by the rest of society, including the appointed gatekeepers of the medical establishment.

“Orlando, My Political Biography” is an example of the kind of movie that rarely gets made or released today, and that wasn’t all that common even during the heyday of quasi-experimental arthouse cinema. Appropriately, considering the subject matter, it refuses to get pinned down to prescribed labels or meanings or even genres, leaping freely between different storytelling modes, sometimes without much of a segue to smooth over the jump. It doesn’t hang together in any conventional way, and sometimes it seems to wander into a cul-de-sac and get stuck. But you always appreciate the refusal to be bound by any preexisting playbook of how cinema is supposed to do, well, anything. It’s a work of fertile imagination that takes every step confidently, even if it isn’t certain where it will lead.