Viola, torn between a man she loves and a woman in love with her as 'Cesario'
TWELFTH NIGHT
The Story: When she washes up on the shore of Illyria after a shipwreck, Viola disguises herself as Cesario, a page to Duke Orsino, with whom she eventually falls in love. But Olivia, the woman Orsino is chasing, ends up falling for Cesario. Viola passing herself as a boy is the root of all conflict in this play. Also, Samuel Barnett is currently playing the role on Broadway. A man playing a woman pretending to be a man. Got all that?
Famous Actors in the Role: Samuel Barnett (currently on Broadway), Amanda Bynes (She's the Man), RoseMary Harris, Anne Hathaway, Helen Hunt, Gwyneth Paltrow (Shakespeare in Love), Fiona Shaw, Imogen Stubbs
Julia, who travels to Milan as a boy, only to find her true love smitten with someone else
THE TWO GENTLEMEN OF VERONA
The Story: Julia, who has promised herself to Proteus, decides to travel to Milan to be reunited with him at the Duke's court. Julia disguises herself as a male page called Sebastian to stay safe on her journey. But when she gets there, Proteus is fawning all over his friend's new girl Sylvia. Julia -- as the page -- goes as far as delivering the ring she had originally given to Proteus to his new love. Turns out Sylvia's not interested, so it all works out in the end.
Famous Actors in the Role: Rosario Dawson, Judi Dench, Clare Holman, Helen Mirren
Mercutio, flamboyant orator and Romeo's BFF
ROMEO AND JULIET
The Story: The reason Mercutio makes our list is because of filmmaker Baz Luhrmann's decision to portray the character as a drag queen in his 1996 movie Romeo + Juliet. But regardless of whether he's dressed in drag, Mercutio's personality is bold and multi-faceted. His character traits often cross typical ideas of gender. Mercutio's not afraid to oppose Romeo's silly obsession with Rosaline. He opines in eloquent verse on Queen Mab. He never turns away from a duel -- to his own demise. He's sexy and dangerous and at the same time a voice of reason. He's all over the map, and for that we love him.
Famous Actors in the Role: Ben Affleck (Shakespeare in Love), Christian Cooke (upcoming movie from Carlo Calei), John Gielgud, Laurence Olivier, Harold Perrineau (Romeo + Juliet), Keanu Reeves
Antony and Cleopatra, who trade clothes in a lovers' game
ANTONY AND CLEOPATRA
The Story: Cleopatra, while reminiscing, tells her companions, "And next morn,/ Ere the ninth hour, I drunk him to his bed,/ Then put my tires and mantles on him, whilst/ I wore his sword Philippan." One of the most passionate couples in literature, Antony and Cleopatra are more than willing to swap gender roles if it means a good roll in the hay. Or, as long as Antony has some coaxing in the form of alcohol.
Famous Actors in the Role(s): Vivien Leigh and Laurence Olivier; Vanessa Redgrave and Timothy Dalton; Frances de la Tour and Alan Bates; Mark Rylance and Paul Shelley; Harriet Walter and Patrick Stewart
Lady Macbeth, takes on the role of a man without ever changing clothes
MACBETH
The Story: Lady Macbeth is the mastermind behind Duncan's murder, stronger and more power hungry than her husband. She sees Macbeth's hesitance to commit the act and wishes she were a man so she could kill Duncan herself. She says, "Come, you spirits/ That tend on mortal thoughts, unsex me here,/ And fill me from the crown to the toe top-full/ Of direst cruelty." She shames her husband into committing the murder by questioning his manhood, saying: "When you durst do it, / then you were a man." Even as we see her fall to pieces in the end, Lady Macbeth is a simultaneously feminine and masculine force of nature.
Famous Actors in the Role: Francesca Annis, Alan Cumming, Marion Cotillard (upcoming film version), Judi Dench, Kate Fleetwood, Keeley Hawes, Vivien Leigh, Jeanette Nolan, Renée O'Connor, Sarah Siddons, Maura Tierney
Jessica, who hides her identity to elope
Portia and Nerissa, who dress as law clerks and dish out justice
THE MERCHANT OF VENICE
The Story: Lots of ladies dressing as men in this play. The first is Jessica, the daughter of the Jewish moneylender Shylock. Jessica disguises herself as a boy to elope with the man she loves, Lorenzo. Pretty straightforward. Then we have the leading lady Portia and her lady-in-waiting Nerissa, who don the guise of law clerks at a trial to settle a debt between Shylock and the merchant Antonio, for which Antonio owes the lender a pound of his own flesh. Portia expertly worms her way around the impending bloodshed, ensures the future happiness of Jessica and Lorenzo, and converts Shylock to Christianity all in one go. Ponder the moral complexities of all that on your own time.
Famous Actors as Portia: Claire Bloom, Caroline John, Gemma Jones, Joan Plowright, Maggie Smith, Sybil Thorndike
Imogen, who cross-dresses to escape being murdered by her own husband
CYMBELINE
The Story: Imogen kicks off the story by marrying a low-class guy named Posthumus against her father Cymbeline's wishes. Cymbeline sends Posthumus off to exile. In Italy, Posthumus meets a slimy man named Iachimo, who makes a bet that he can seduce Imogen. She's not having it, but Iachimo tricks Posthumus by sneaking into Imogen's room and stealing one of her bracelets. Posthumus believes Imogen has been unfaithful and orders his servant to kill her. She finds out and disguises herself as a boy so she can find her husband and tell him the truth. The moral: Have pants, will travel.
Famous Actors in the Role: Peggy Ashcroft, Judi Dench, Helen Mirren, Dakota Johnson (Ethan Hawke's upcoming film), Vanessa Redgrave
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