would be gripped by what he called automatic writing, during which he transcribed communications from the Other Side. He also received messages from his dead uncle, from the English philosopher Henry More (1614–87), from an inscrutable entity called Wardor, and occasionally from Count Alessandro di Cagliostro. Some of these spirits rather sensibly urged Pessoa to stop masturbating and encouraged him to lose his virginity. He ignored their advice. Pessoa himself ridiculed the idea that actual spirits were getting in touch with him, but said he liked the fact that he could ask them for advice. They provided him with the social contact he couldn’t get from real people. For Pessoa, the only true reality was the one he (or, in this case, Soares again) created for himself:

The experience of life teaches nothing, just as history teaches nothing. True experience consists in restricting our contact with reality and increasing our analysis of that contact. In that way our sensibility extends and deepens itself, because everything is within us; all we have to do is look for it and know how to look for it.

Pessoa was twenty-six when he was first seriously “possessed” by one of his heteronyms. He was standing beside a chest of drawers when he was overcome by the urge to write poetry. Standing upright at the chest he pumped out thirty poems in quick succession, titling the collection “The Keeper of Sheep” and signing it “Albert Caeiro.” He compared the experience to being in a trance, saying “my master had appeared inside me.”

The literary critic Cyril Connolly once said that Pessoa “hived off separate personalities like swarms of bees,” but these were only apparent on the page: They were never shared with anyone else. Pessoa was a loner. He dined in the same restaurant every day for thirty years.

If after I die, they want to write my biography, There is nothing more simple. There are only two dates: my day of birth, day of death. Between one and the other all the days are mine.

Eerily, it was Alvaro de Campos (the monocle-wearing existentialist) who said, “Fernando Pessoa, strictly speaking, didn’t exist.” The man called “person,” with over a hundred different personalities, spent almost his entire life denying his own existence.

Like so many bright children denied proper affection from their parents, Pessoa read his way out of the lonely realities that surrounded him. The bustling pages of Dickens were a particular favorite:

There are children who really suffer because they weren’t able to live in real life with Mister Pickwick and could not shake hands with Mister Wardle. I am one of them. I have wept real tears over that novel, for not having lived in that time, with those people, real people.

Again this is not Fernando Pessoa but “Bernardo Soares.” Pessoa read the novels but Soares wrote about them. When reading any of Pessoa’s authors, the constant danger is to mistake the mask for the man. Though Soares wrote “I will never write a page that will reveal me or reveal anything else,” Pessoa actually revealed a great deal. He is a unique writer—one who can be uniquely described as “multiply unique”—because he delivers so many different styles, so many ideas, such a rich mix of insights and possibilities. It’s almost as if he created his own self-referential literary tradition as both inspiration and company. His own life might have been sad, short, and tragic, but every bit as much as Florence Nightingale or Daniel Lambert, he—or rather his team—turned his misfortune into something of lasting value:

If a man only writes well when drunk, I would tell him: Get drunk. And if he said to me that his liver suffers because of that, I would answer: What is your liver? It’s a dead thing that lives as long as you do, while the poems you write live forever.

If Fernando Pessoa had more selves than he could handle, the English writer Dawn Langley Simmons (1937–2000) had only one, but she had two different bodies. Her life veered wildly between vaudeville and Greek tragedy, beginning as Gordon Langley Hall, the illegitimate son of Vita Sackville-West’s chauffeur. Later she was adopted by the English character actress Margaret Rutherford and had one of the first sex-change operations performed in America. In 1969 she broke another taboo by marrying her black butler in Charleston, South Carolina, the first legal mixed-race marriage in the state. As one of her obituaries commented: “It is a measure of the ascending scale of prejudice that, of all her transgressions, it was her crossing of the racial divide that most shocked her Southern neighbors.”

Dawn Simmons was born either with both male and female genitalia, or—as she always insisted—with female genitalia that an adrenal abnormality had caused to look male. In any event, although she always felt female, her family brought her up to be a boy called Gordon. “He” was raised by his grandmother Nelly Hall Ticehurst and spent the holidays at Sissinghurst, home of Vita Sackville-West and Harold Nicolson. As a small boy, their son, the writer and publisher Nigel Nicolson, played with Gordon, known to everyone as Dinky. Sackville-West was famously the inspiration for Virginia Woolf’s novel Orlando (1928), in which a boy is transformed into a beautiful woman. Simmons would later write in her autobiography: “Had she lived a little longer, Vita would have been intrigued to know that the child ‘Dinky,’ as she called me, would become a real-life Orlando.”

Gordon started writing early, having his first poem published at the age of four and his first interview— conducted sitting in Mae West’s lap—appearing in the Sussex Express when he was nine. In 1953, his grandmother died and he emigrated to Canada, becoming a teacher on an Ojibwa native reservation. Despite having had periods through “her” teens and “his” voice not having broken, Gordon still at this stage appeared male, and he wore a crew cut. He turned his experiences with the Ojibwa into a bestseller, Me Papoose Sitter, published in 1955, and soon after moved to New York, where he worked as a journalist and society biographer, writing critically acclaimed lives of Mary Todd Lincoln, Princess Margaret, and Jackie Kennedy. Witty, eccentric, and ostentatious, Gordon made friends across a very broad swath of New York society, from fellow writers like Carson McCullers to actresses like Joan Crawford and sportsmen like the boxer Sugar Ray Robinson. A distant relative, the wealthy painter Isabel Whitney, took to him at once and invited him to live with her in her West Tenth Street mansion. Here Gordon met Margaret Rutherford, the matronly actress still best remembered as Madame Arcati, the medium in the 1945 film of Noel Coward’s Blithe Spirit. Rutherford had come hoping to be cast in the role of the grandmother in the proposed film of Me Papoose Sitter, but was immediately smitten by the person of Gordon himself. She described him as “a child… with large brown eyes inherited from some long dead Andalusian ancestor… a large green and red Amazon parrot named Marilyn on his shoulder.” When Isabel Whitney died of leukemia in 1962, Margaret Rutherford and her husband legally adopted Gordon. He was twenty-five.

Whitney left Gordon her house and $2 million estate. He used the proceeds to buy a faded 1840s pink stucco mansion in the gay neighborhood of Charleston, South Carolina. Gordon displayed impeccable interior design sense, filling the house with Chippendale and early American furniture and transforming the garden with designs sent over by Vita Sackville-West. He was regarded as a fixture in Charleston high society: an eligible, if undeniably camp, bachelor. He once threw a coming-out party for two of his dogs, where the pooches were displayed on velvet cushions, dressed in chenille, long gloves, and pearls.

Then, in 1968, it all changed. Gordon checked himself into the brand-new Gender Identity Clinic at Johns Hopkins University in Baltimore and underwent corrective genital surgery and a course of counseling. One of the psychiatric reports noted with a hint of foreboding that despite her high intelligence, as far as men were concerned, the newly female Dawn had “the mind of a fourteen-year-old girl.” So it was to prove. She returned to Charleston as Dawn Pepita Hall, sporting “a Dippity-Do hairstyle—a dowdy doppelganger of Jackie Kennedy” according to one neighbor—and within a very few months announced her engagement to a black motor mechanic, butler, and aspiring sculptor, John-Paul Simmons. “His black hand touched my white one; it was as simple as that,” she wrote in her autobiography.

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