‘What do we actually fall in love with?’: Why ‘Twelfth Night’ is Shakespeare’s ‘Queerest’ play

Shakespeare, but make it Queer – that’s the vibe of an upcoming performance of Twelfth Night that is set to take over Toronto’s High Park on Friday. 

One of the biggest and longest-running outdoor professional theatre events across the country, Dream in High Park draws over 30,000 people to High Park Amphitheatre every season. 

The beloved production is inclusive and family-friendly, providing access to art that engages the local community while bringing the stories of Shakespeare to another generation of theatre lovers.

This week will see hundreds of attendees gather at the venue for a special Queer night of Dream in High Park, which will see one of Shakespeare’s most beloved comedies in a special performance that includes a curated, welcoming space for members of Toronto’s 2SLGBTQIA+ community.

In an interview with Queer & Now, Canadian Stage Artistic Director Brendan Healy explained that the show’s main themes, including identity, gender and love, allow for the centuries-old play to resonate with Queer audiences of the contemporary age.

While the Friday performance holds true to the original story of Twelfth Night, Healy explained that hosting a Queer event is less about changing the story and more about creating a space where people from our community can be together to enjoy a Shakespeare play. 

Unlike a reimagined production, the performance itself remains unchanged. Instead, the evening is designed to foster community, with drag performer Hollywood Jade introducing the show before audiences settle in beneath the stars.

Twelfth Night: Shakespeare’s ‘Queerest play’

While Twelfth Night isn’t explicitly about 2SLGBTQIA+ identities, Healy calls the production Shakespeare’s “Queerest play.” 

The comedy, believed to have been written in 1601-1602 before being published in 1623 as part of a collection of plays now known as the First Folio, revolves around mistaken identities, gender disguise and unconventional romance. 

The storyline follows Viola, who disguises herself as a man, embarking on an adventure that includes a constellation of romantic entanglements that challenge assumptions about attraction and identity.

Healy explained that to him, those questions feel remarkably modern.

“What do we actually fall in love with?” he questioned. “Do we fall in love with a body, with a gender, with a soul?” 

The artistic director noted that originally, Shakespeare’s original productions actually unintentionally (or perhaps intentionally…) took gender performance even further, with young male actors dressed in traditionally female clothing and hair styles, portraying the women characters. 

In Twelfth Night, this would mean a male actor, dressed as a Viola, a female character, who then disguises herself as a… man. Healy describes this as an early exploration of gender performance.

Director Gregory Prest believes those themes are part of what continues to draw 2SLGBTQIA+ audiences to the show. 

Prest also notes that Twelfth Night includes one of the few openly Queer-coded characters in Shakespeare’s catalogue of shows, Antonio, adding another layer of significance for 2SLGBTQIA+ audiences.

Dream in High Park Queer Night: Inspired by community

The Canadian Stage artistic director shared that the idea for Queer Night grew from the company’s belief that theatre is as much about community as it is performance.

“Theatre as an exercise is essentially a community-building exercise,” Healy explained. “As a Queer person myself, I love being in groups. There’s something really special about being among other people from my community.”

He said experiencing Twelfth Night in a Queer-majority audience changes what parts of the show resonate with viewers, what things feel funny, what feels relatable, and overall how the story is received.

Overall, Prest shared that he hopes audiences of all backgrounds continue to find themselves in Shakespeare’s work over 400 years after the show was first published.

The director describes the production as funny, heartfelt and ultimately hopeful, beginning with grief and shipwreck before showing how love has the power to transform people’s lives and open them to new possibilities.

For Healy, that’s ultimately what makes Shakespeare’s work timeless.

“Love exceeds categories,” he said. “Love actually breaks categories… It’s a really disruptive force.” 

While it’s impossible to know exactly how Shakespeare understood sexuality 400 years ago, Healy believes the playwright’s exploration of love as something that challenges societal expectations remains deeply relevant today.

General admission tickets are available on the Canadian Stage website, priced at $35 for adults and $20 for those 16 and under.