The following seven pieces of literature explore curious and challenging tales of cross-dressing, intersexuality and gender-shifts, in ways that educate, entertain and enlighten. From the Shakespearian comedy to the epic spoken word poetry of the compelling Kate Tempest, gender roles are challenged and the normative is upended.

The great philosopher Simone de Beauvoir wrote in The Second Sex that "one is not born a woman, but becomes one". This brief statement expresses the performativity of gender like no other: how we learn gender from social and cultural clues, and furthermore, de Beauvoir questions the innateness of gender being aligned with biological sex – I know, all this from one line... With that in mind, let's explore literary gender bending:

 

As You Like It – William Shakespeare (1603)

As you like it - William Shakespeare

As You Like It is one of Shakespeare’s lesser performed comedies; despite the rumour that the great Bard himself took a starring role. During the course of the play, the exiled Rosalind spends four acts disguised as a young man named Ganymede who, becomes the focus for the amorous attentions of the marvellously rustic Phebe. But Ganymede – or should I say Rosalind – only has eyes for Orlando. Ganymede befriends Orlando and counsels him in love, giving him tips on how to win his sweetheart Rosalind.

Shakespeare turns up the humour with mistaken identities; manipulating gender and switching costumes all while the audience is in on the secret. Yet what makes this play most interesting is thinking about its original historical context. Women were not allowed on stage during the era in which the play was performed. Therefore beautiful Rosalind would have been played by a young boy, who, then dressed as a girl, would disguise herself as a man. In some scenes ‘Ganymede’ pretends to be Rosalind – stay with me – so we have a boy actor, playing a girl, Rosalind, who disguises herself as a man, Ganymede, who pretends to be Rosalind. Tricksy, confusing, and subversive!

 

The Monk – Matthew Lewis (1796)

The Monk Matthew Lewis

Matthew Lewis’s scandalous gothic novel The Monk is a rip-roaring Victorian bestseller, no doubt due to the twisted relationship between the titular monk Ambrosio, and the young and pious convert Rosario.

As a devoted and secretive young boy, Rosario is abandoned at the monastery by a well-dressed stranger and Ambrosio takes the foundling under his devout wing. During a moment of confidence the young devotee confesses to his elder that he is in fact Matilda, a beautiful young woman who idolises the monk’s saintly figure. Flattered by the beautiful young woman he decides that she must leave before a scandal breaks out, and picks a rose for her to remember him by. As he plucks the flower he is bitten by a poisonous snake. At the brink of death, Matilda sneaks into the dying monk’s cloister and ‘heals’ him, revealing both herself and her supernatural powers to the desperate man. 

 

Orlando – Virginia Woolf (1928)

Orlando - Virginia Woolf

Orlando is Woolf’s incredible novel about the fluidity of gender and time. Spanning three hundred years in one lifetime, the novel begins in the Elizabethan period when Orlando the nobleman becomes the favourite of the Virgin Queen. After the Queen dies, Orlando soon falls for the ice skating Russian princess Sasha but Sasha is unfaithful. After suffering dejection, Orlando sleeps through three long days during the Civil War and on arising finds that he has become a woman. While Woolf’s narrator seems uneasy about the shift, Orland takes it in her stride. While biologically female, Orlando shifts between genders, dressing as both men and women and only finds happiness in falling in love with a similarly non-conformist sea-captain – the excellently named Marmaduke Bonthrop Shelmerdine.

 

Top Girls – Caryl Churchill (1982)

Top Girls - Caryl Churchill

To celebrate top girl Marlene’s promotion to managing director of a recruitment agency, she throws a dinner party, inviting five women from history. Pope Joan, an aloof, intellectual, and an incredible theologian, is one of those guests. Joan tells the other women about her life: from the age of twelve she would dress as a boy so she could continue to study, then lived as a man for the remainder of her life, while continuing to take male lovers. Working her way up through the Catholic Church, Joan was eventually elected Pope: she describes how she had to rid herself of her female body to succeed. Unfortunately, she became pregnant by her chamberlain lover and delivered her baby during a papal procession.

 

Cock and Bull – Will Self (1992)

cock and bull - Will Self

Will Self’s pair of novellas explore gender in a fantastical yet entirely mundane way; critiquing gender theory as he goes. The first, Cock: A Novelette begins with Carol, a woman who often takes the line of least resistance; for example wandering tipsily into an unsatisfactory and dull marriage with Dan, an alcoholic. Dan manages to diminish all Carol’s female urges and they exist unhappily. But surprisingly, Carol begins to develop both psychological and physiologically in a dramatic and catastrophic way totally altering her perceptions of her effete husband and his Alcoholics Anonymous mentor.

The second novella, Bull: A Farce, features eponymous character Bull – a man’s man.  He wakes up having grown a very female ‘primary sexual characteristic’ behind his knee. The rugby player, unsure of his new development, seeks medical assistance, with sinister results. 

 

Middlesex - Jeffery Eugenides (2002)

Middlesex - Jeffery Eugenides

Eugenides memoir novel was inspired by the real-life memoir of 19th-century French hermaphrodite Herculine Barbin. Blending autobiographical details alongside mythology (in order to flesh out the life of Herculine), Cal, the intersex narrator is brought up as a female but discovers she is intersex after being involved in an accident. Eugenides’s novel is an epic that covers the complex lives of three generations of Greek immigrants – Cal’s ancestors – in America, and the biological and social impact they have on her life. Alongside inspiring Eugenidies, Herculine was also the inspiration for another of the list’s authors: Caryl Churchill based the play A Mouthful of Birds on Herculine Barbin’s memoirs.  

 

Hold Your Own – Kate Tempest (2014)

Hold Your Own – Kate Tempest

Kate Tempest’s awesome collection of poetry Hold Your Own transforms both the mythical story of Tiresias, and the formal traditions of poetry into something exciting and very modern. The poem narrates the tale of a 15 year old boy who, avoiding school, walks into a woodland and in the clearing witnesses a pair of copulating snakes. Unsure, and still angry from being taunted by the kids at the bus-stop, he strikes out at the serpent pair. The Goddess Hera sees his actions and decides to punish the young man by turning him into a woman. The four cycles of poetry in this collection consider childhood, what it means to be a man and what it means to be a woman.

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