Oliver van Diepen’s experiences as a trans artist
Born and raised in a strict Christian home, Matthew Oliver van Diepen did not even know transgender people existed. Then, just before entering high school, a friend came out to him.
“I had no idea what it meant. But as a good Christian friend, I googled it.” When Oliver read the definition the first thought that came to his mind was “there are other people like me.” Oliver spent the next three years trying to figure out if that gut reaction was real.
At the beginning of grade twelve, Oliver made the brave decision to come out to his parents.
“I did not know if I was going to get kicked out or not, so compared to that, it went very well.” After six years, Oliver and his parents are still having conversations about names and pronouns. “They’ve come a long way and we still want to have a relationship. But it’s hard.”
After high school, Oliver moved to Calgary and was in a serious relationship. There, he started working on socially transitioning and gaining knowledge about transitioning medically and legally. When the relationship ended, Oliver legally changed his name.
As a talented actor, singer, and dancer, Oliver engaged in musical theatre and drama throughout high school, performing in many leading roles. In 2015, Oliver was accepted into the Rosebud School of the Arts, located in a hamlet with a population of roughly 88, where he began to explore the ways in which he could express himself through art and performance.
Oliver found a lot of support from his classmates and a few teachers. “I lived with an amazing family for three years. They called me my name and jokingly referred to me as their son. It was the first time I had been called that.”
However, attending theatre school in the small rural community of Rosebud presented many challenges. “My trans identity impacted every single part of being there,” says Oliver. “I was their first trans student, so first the board had to decide whether they could even allow me to attend, and then they had to have special meetings to figure out everything else.”
As one of the only queer people in Rosebud, Oliver found the experience isolating. “People did not really know what ‘trans’ meant, and they were scared of offending me. Because of that, they treated me differently than everyone else.”
Oliver has faced similar challenges for his whole life.
“I have been the first trans person in two different schools, one youth group, several summer camps, and within my family,” says Oliver. “I have faced horrific transphobia and homophobia, and scarring discrimination of all kinds.”
Most of the discrimination, he believes, comes from ignorance and fear, and prejudiced ideas of what ‘trans’ means. “Unfortunately, a lot of it is shadowed in the media,” says Oliver. “I wish when I was growing up I had been able to see people like me make it to the end of a movie alive and be more than just comedic victims of ignorance and lies.”
In the summer before his third year, drag performance came into the picture. While Oliver was recovering from top surgery, he attended a drag show in Calgary. One month later, he was part of the action, and his drag monarch persona “Oliver Twirl” was born.
It was through drag that he began to discover people who understood what he’d been through. “They had similar experiences with gender,” says Oliver. “It was an amazing and safe place to talk about it and create art together.”
After his introduction into the drag world, Oliver found himself auditioning for Transformance, a musical about two transgender individuals who develop a relationship. Reading Transformance was the first time Oliver saw a trans person in a script who wasn’t dehumanized, which he believes is a problem.
“Transformance was the safest audition and rehearsal space I’ve ever been involved in. I was surrounded by people who genuinely trusted that I was there and ready to work and that I would give everything I could,” says Oliver. “Some of the issues we tackled were very close to all of our hearts and experiences.”
Soon, Oliver began to contemplate whether he wanted to continue his theatre training in Rosebud. “It felt like people in Rosebud didn’t trust me to be there or to work hard,” says Oliver. “I think Transformance was the key reason why I decided to leave. I wanted to create queer art, and that wasn’t happening there.”
After making his decision, Oliver moved back to Calgary, where the drag community welcomed him with open arms.
Oliver joined the Fake Mustache Drag Troupe and has since performed in over fifty shows. “Drag was a crucial thing for me to find. It is an open place to be myself without fear of judgement or being met with confused stares,” says Oliver.
Oliver sees drag as an empowering way to explore gender identity. “I was so scared and focused on passing as male and being ‘safe’ that I didn’t really give myself time to explore the opportunities and expressions that were inside of me all along,” says Oliver.
Twirl has also given him an avenue to express himself in many ways. “I love being a ‘gender fucker’ and a drag monarch,” says Oliver. “Through my drag I show the uncomfortable and sad parts of being queer. But also there’s lots of fun, joy, and silliness to be had.”
Oliver says he has found a family in the drag community. “Everyone is so amazingly supportive of the individuals behind the art. It’s an inclusive space to learn, discover, and try whacky new things,” says Oliver. “I’ve found safety in the Fake Mustache Troupe.”
For Oliver, drag is one way to address political issues and to encourage discourse in an open environment. “Drag isn’t the be-all and end-all, but the people in this community have been working so hard for equality, safety, and justice,” says Oliver.
In light of recent events in the United States and the ongoing reality of transphobia, Oliver thinks that allies need to start educating themselves. “We need to help one another survive and speak up about injustices. We won’t let a bully win.”
Oliver believes that artists are the soothsayers and prophesizers of the world. “We have been given skills to see and talk about issues in the world in more frank and startling ways than most people,” says Oliver. “Drag shows are a way of opening people’s eyes to the spectrum that is humanity.”
Oliver hopes that people will support LGBTQ+ artists. “Many people in the queer community are working to create hope for the younger generation through art,” says Oliver. “We need to reach out to queer artists and promote their work.”
Oliver proudly identifies as transmasculine, polyamorous, panromantic, and demisexual.
“Everyone deserves to be who they are, and to be loved and supported for who they are. Find your family and grow strong with them,” says Oliver. “Coming out was the best decision I ever made.”