Men. Women. A man who transforms into a woman across several centuries. A bi-millennial vampire drained of inspiration. A cryogenic company CEO in the year 2151. A crime-covering mother. A conniving lawyer. The White Witch. A balleticwitch. Gabriel the Archangel. The Ancient One. Social Services. Twin sisters. Amy Schumer’s boss.

Since 1986, Tilda Swinton’s unparalleled eclecticism has enlivened stories about drinkers, sailors, soldiers, spies and so much more. This month, Midwest Film Journal staffers and contributors look back at the wild, weird and wonderful ways this Oscar-winning actress and international treasure keeps it going Tilda Break of Dawn.

The closest I ever got to acting was playing the butler in And Then There Were None in a rural high school in northern Indiana — where we painted the sets over and over and over and the costumes were what we brought from home.

Intermission offered punch and those little cookies no one likes but everyone buys. Acting as action, as something with intentional choices, was as foreign to me then as music, baking or being in a large crowd are to me now. It was something I played at without direct purpose — content to pretend along, to simply memorize and to deliver results without thinking. The role I had was a mask and nothing more. There was no thought in my mind to draw anything from reality into it, let alone having anything in my own life to draw from in order to play a somewhat duplicitous English butler.

Acting is damned hard work.

So it is with pleasure that I write about a performance that is not merely an instance of a role being made for an actor and an actor being born to play it, but a performance that blurs the very line line between actor and character. It is a role that demonstrates effortlessness, like watching Sophie Druml play Chopin’s Étude Op. 25, No. 11 blindfolded, Duff Goldman slap together a croquembouche or literally any normal human at a party.

To appreciate Tilda Swinton’s work in Orlando, it is best to start at the beginning — with Orlando itself. Virginia Woolf’s novella, Orlando: A Biography, was published in 1928 to critical success, ensuring Woolf’s financial stability. This success came partly because of Woolf’s immense writing talent but also because Orlando was seen as a tantalizing peek into the life of Woolf’s lover, fellow writer Vita Sackville-West.

As good lives often are, books upon books can be written about Sackville-West and the relationships that touched her. But we focus on Orlando, initially conceived in a 1927 diary entry by Woolf who wrote: “And instantly the usual exciting devices enter my mind: a biography beginning in the year 1500 and continuing to the present day, called Orlando: Vita; only with a change about from one sex to the other.” Sackville-West was an exquisite subject for what would become a long love letter and herself strode the line between the masculine and the feminine, sometimes dressing in different clothing and taking the moniker Julian.

Thus Woolf gave the world a book that Swinton would pick up and read as an adolescent and find to be a “practical manual,” an “interactive biography of [her] own life and future,” “the most transgressive experiment [Woolf] ever made,” and, finally, cause to note that “[her] own relationship with Orlando is complex and entwined, a kinship’s entanglement.”

And from that, Swinton helped give us 1992’s period drama featuring the lead actor in full androgynous glory.

I cannot imagine how meaningful this role was to Swinton — first because I am not an actor. I have never plunged into the depths of myself to extract a new humanity for a role. But also because I’m a cishet white dude in the Midwest whose biggest obstacles in life have been social anxiety and being a little unhappy most of the time. Swinton, on the other hand, is one of the most famous faces of gender fluidity, having most solidly described herself, once again comparing to Orlando, as “probably a woman” and, much more often, choosing to eschew gender in deeds if not in words. In 2019, Swinton curated an art exhibit inspired by Orlando and included the statement: “I have come to see Orlando far less as being about gender than about the flexibility of the fully awake and sensate spirit. In Orlando, fluidity is not an aberration but an inextricable element of human experience.”

This is what is most fascinating about watching Orlando while living in an emerging postgender world. Gender is so ingrained into our worldviews that we cannot help to see it, especially as we try to undermine it. Some define themselves within it and against it. And some, like Swinton, leave it for something else.

To see this reflected in a book written in the 1920s and a movie made in the 1990s reminds us that radicalism is sometimes deceiving and, when most effective, nudges us over the edge and deconstructs completely what seems most obvious.

Arguably Orlando is the first transcentric novel in English. Of course, artists played with the shiftability of form before then, if not to the same degree. Ovid’s and Kafka’s separate Metamorphoses, The Arabian Nights and Shakespeare all featured doubling, switching and changing in some way. Woolf’s work and, by extension, the film, goes another step by deleting the delineation almost altogether.

Writer-director Sally Potter amplifies these traditions and this deletion — for instance casting Quentin Crisp, whose life John Hurt portrayed in the film version of The Naked Civil Servant, as Queen Elizabeth I. Here then, the audience gets Crisp, a person born a man playing a woman, interacting with Swinton, a person born a woman playing a man who will turn into a woman — with both actors never fully ascribing to any gender throughout their lives. Like Swinton, Crisp defied labeling. He wrote in his autobiography, The Last Word, that he, at the age of 90, would probably best be described as a woman but kept hold of his masculine pronouns throughout. Is this casting “doubling” per se, in the Shakespearean sense, or should it be thought of as an accentuation of gender as mere construct? As soon as we examine what is happening, the concepts fall apart. We may as well try to arrest flowing water with only our sight.

Orlando, the role, of course comes naturally to Swinton because of all the above, but the subtleties of her choices amplify her talent as an actor.

Swinton has described Orlando to be about growing up as much as it appears to be about eternal youth. And at first, Swinton plays the role of an awkward, encumbered youth, too privileged to really understand the world outside of his own ego but who seeks to write poetry of it. Swinton masters the awkward confidence of a developing male excellently, most noticeable in Orlando’s gaits through time.

Swinton’s big, searching eyes — which convey so many other emotions in other films — also show the subdued complexity of Orlando’s emotions, the confusion and fear and curiosity all at once. It’s a feature Swinton has always used with expertise, even when her face is blank and emotionless and unreadable and severe; she has these eyes that cut right to the center of the characters she plays.

As Princess Sasha is introduced as Orlando’s love interest, in a scene that reminds one of Levin spying Kitty Schtscherbazkaja on the ice in Anna Karenina, those eyes display a youthful hunger and desire. As the queen and Orlando’s father perish, Orlando’s sadness is almost bewitching, causing others to remark “Mourning quite becomes him,” shaded well with Swinton’s expressive expressionlessness. When Sasha breaks Orlando’s heart and he turns to poetry only to be ridiculed in verse by a fellow poet he is a patron for, Swinton smolders again with prideful, masculine-bounded emotion:

“Try as he might, this gracious noble Lord

Who lifts his pen and thinks he then can write

Cannot — for who can pen when he is bored?

The mind of leisure only can be trite.

This pretty knight who feebly lifts his sword

To make a witless thrust against his doom

Is foiled by what his noble birth affords —

Dogs, dogs, more dogs, and far too many rooms.

So fortune smiles on those who own the land

And frowns at trivia from the dabbler’s hand.”

Throughout the film, Potter has Swinton break the fourth wall, looking directly into the camera with these eyes and reminding us who exactly we are watching. Before and after Orlando’s transformation, their deadpan deliveries keep us anchored to who Orlando is as a person.

Orlando as a film is a bit of a slow burn. It has to be if it’s going to cover 400 years of an immortal, gender-fluid noble. Orlando as woman only comprises the last quarter or so of the film and, though a bit rushed in places, carries on well by allowing Woolf’s writing to shine through and letting Swinton’s duality create explicit contrast with our concept of gender.

While Orlando does face more gendered conflict — “The chief charges against her were (1) that she was dead, and therefore could not hold any property whatsoever; (2) that she was a woman, which amounts to much the same thing …” — she manages the change almost playfully. Upon waking to find herself transformed into a woman, Orlando remarks with the same deadpan way as before: “Same person. No difference at all. Just a different sex.” The dual role allows Swinton to ultimately call to attention that a person is not the various trappings we have concocted to help us make sense of a chaotic world.

For too many of us, roles expand to more than the stage, and the masks that we develop to hide depths too deep to plunge sometimes blind us to the catharsis Orlando experiences at the end. Orlando states, after hundreds of years of misfitted poetry and nobility, “I never felt better in my life” after declaring herself nature’s bride and finding solace in the first lover since Sasha (Billy Zane’s Shelmerdine) — a denouement worthy of another essay by itself.

We talk so much, and I’ve written before, about how the really truly wonderful thing about movies and music and art is that we can get to new truths after our exposure to them. For Tilda, it was being an adolescent who saw themselves in words a half-century old, perhaps getting further permission to develop an even more genuine version of the self. For the rest of us, perhaps through Woolf’s words or Swinton’s performance or any other motley arrangement of experiences and art we have, we can break down the boundaries of the supposed to and finally explore ourselves and this world freely.