Image caption: Dramatic Arts graduate Oliver Webb Wilkinson (BA ’25) celebrated his academic achievements as well as his journey of self-discovery through artistic creation during Brock’s 117th Convocation.
Wednesday, June 11, 2025 | by Gillian Minaker
Oliver Webb Wilkinson (BA ’25) will never forget the first time he stepped on the Marilyn I. Walker Theatre stage as his authentic self: a transgender man.
At the end of his first year studying Dramatic Arts (DART) at Brock’s Marilyn I. Walker School of Fine and Performing Arts (MIWSFPA), Webb Wilkinson realized he was not quite who he thought he was.
“I entered first year living in residence a regular city girl, but quickly realized something was different for me,” he said.
Webb Wilkinson embarked on a winding — and joyful — journey of self-discovery.
“All of my professors and classmates were so supportive as I was figuring out what was happening in my head and heart. How could I marry what my soul is with what my body is? The path is different for every trans or gender-queer person,” he said.
Brock’s Student Health Services team helped Webb Wilkinson navigate important health information and access resources, support that Webb Wilkinson was grateful for as he began his medical transition.
Oliver Webb Wilkinson (BA ’25) performed alongside fourth-year Dramatic Arts students and members of Peregrine Theatre Co. in “Mementos,” which explores themes of hope and amidst life’s challenges. From left are Megan Mastantuono, Simon Bell, Webb Wilkinson and Maddox Keller.
“Partaking in the creation of who you are is a beautiful, empowering thing; truly feeling who you are and seeing it outwardly is magic,” he said.
Studying theatre at Brock, with a Concentration in Performance, allowed Webb Wilkinson to explore themes of identity through creativity and playfulness.
“Failure doesn’t exist in DART; if things don’t work, you try something else. What I will remember is the sense of play and lack of judgment in classes,” he said. “Trial and error is part of making theatre, we learn from things that don’t work.”
Through Brock co-op opportunities, Webb Wilkinson worked every summer at professional theatre organizations, including Crane Creations Theatre Company as Artistic Producer, Pirate Life Theatre as a performer and recently Theatrix Costume House in Hamilton as an intern.
These experiences gave Webb Wilkinson a sense of what his future workplace would look like and allowed him to benefit from professors who are theatre makers and learn from professionals like DART’s Head of Wardrobe Bobbi Pidduck, who works in wardrobe at the Shaw Festival.
“It’s school theatre at a professional calibre, and there is nothing like a mainstage at Brock,” Webb Wilkinson said.
In the DART 2023 mainstage production of A Vampire Story, Webb Wilkinson played his first role as a male character, and said the creative team led by Director Gyllian Raby were completely open to his interpretation of masculinity.
“It was an incredible and affirming moment for me,” he said.
In his final year, Webb Wilkinson explored his interest in costuming as the Assistant Designer for the Department Mainstage Scorched, mentored by Head of Wardrobe Bobbi Pidduck and production designer and faculty member, David Vivian, and also played key roles in the DART 4D56 production Mementos, a student-led production guided by Associate Professor Mike Griffin.
“We were so lucky to have Professor Griffin guiding us as we wrote and mounted Mementos,” he said. “I spoke with him a lot about the growing stress of being trans at a time when there is increasing oppressive legislation targeting the trans and queer community — but at the same time, experiencing the joy of being loved and supported by your family and friends.”
Webb Wilkinson wrote characters reflecting these themes into the play. He said a line in Mementos summed it up for him.
“‘Now, you get to exist the way you want to’: to write those words and perform them was life changing. Theatre speaks to people in profound ways, and Brock gave me that chance to communicate with audiences whose stories were similar,” Webb Wilkinson said.
This summer, Webb Wilkinson will be working in Toronto with MERCHANT, a production company specializing in commercials and collaborations with advertising agencies. He will help build storyboards, check and book film locations, conduct research on props and costumes and be a production assistant on set.
Webb Wilkinson said he’s become a whole different person in the best way possible at Brock.
“The University has been such a kind and wonderful environment. I don’t want to leave, but Brock has made sure I’m prepared to go.”
