Mourning Behind the Mask: The Sharp Comedy of Ollie Maddigan

“I would never say I was brave for putting the show on. I was terrified the whole time I was writing it, and even more terrified performing it.”

Ollie Maddigan is refreshingly suspicious of the word “brave.” In an arts landscape that often treats personal trauma as a currency for critical acclaim, the writer and performer of The Olive Boy—arriving at Southwark Playhouse this January—is quick to dismantle the idea of himself as a courageous martyr.

For Maddigan, putting his mother’s death on stage wasn’t a grand act of heroism; it was the practical, if terrifying, result of a writer following the age-old advice to start with what he knew. “I still remember standing backstage before the first ever show in 2021, honestly convinced I was about to throw up,” he admits.“The only thing that kept me going was that I wanted to be a writer, and every writer is told to start with what they know. So I did.”

What he knew was a 15-year-old boy in the immediate, messy aftermath of loss.

The Olive Boy finds its protagonist sent to live with an estranged father, starting a new school, and attempting to reinvent himself through a desperate, often disastrous quest for a first girlfriend.

It is a story of survival through a constructed identity, a teenage “act” designed to mask the vacuum left by his mother’s absence.

“I would never say I was brave for putting the show on. I was terrified the whole time I was writing it, and even more terrified performing it.”

Maddigan is clear that the character’s rougher edges—the stupidity, the casual sexism, the harmful posturing—are deliberate. He noted that even the “brilliant” kids at that age still talk like fifteen-year-olds, and to sanitize that for a middle-class theatre audience would be a lie. “That is just how we are at that age,” Maddigan says. “So if I was going to write a character who was fifteen, he had to sound fifteen. That means he sometimes says things that are stupid or harmful or a bit sexist even, because that is what boys pick up from the world around them. But even with all of that, The Olive Boy is never a bad kid. He is just lost. The same way most of us were at that stage in our lives.”

The Architecture of the “Act”

The play’s evolution from its 2021 debut to an Offie-winning production has been swift, but Maddigan remains grounded regarding the “bittersweetness” of his success. While he acknowledges the show has “opened doors” and provided a creative outlet for his pain, he is adamant that professional milestones do not equate to personal healing. There is a steeliness in his refusal to let the industry “fix” his grief for the sake of a happy ending.

“Grief is an entirely personal landscape,” he explains. “No success, no praise, no show can rewrite what happened or how it felt. The only thing that can shift the way you carry that weight is time and the work you do within yourself.”

Structuring that weight into a cohesive narrative for the Southwark run is a collaborative effort with director Scott Le Crass. Though rehearsals are in the early stages, the pairing is rooted in a shared history; Le Crass also lost his mother at a young age. Maddigan suggests this connection allows for an understanding of the script that “goes far beyond the page,” capturing the specific alchemy where humour and hurt exist side by side. “He gets the humour, he gets the hurt, he gets the mix of both living side by side,” Maddigan says. “I am genuinely excited to be in the room with him. I think the work we make together will come from a place of real understanding.”

Adding a layer of external pressure to the protagonist’s internal wall is “The Voice,” a therapist character recorded by Ronni Ancona. She represents the adult world’s well-meaning but often intrusive demand for “processing,” a sharp contrast to the character’s instinctual need to hide behind a mask of normalcy.

Honesty Over Confession

The play is built on a “comedy first” foundation, though Maddigan admits that even when leading with humour, you cannot hide the truth. “The balance in the show happened on its own. I always knew it would be a comedy, so I focused on making it as funny as I could. But even when you try to lead with humour, you cannot hide the truth underneath it. The sad parts find their way through, even while people are laughing.”

Yet, for all its reported honesty, The Olive Boy is not a total confession. Maddigan admits to editing the script based on privacy rather than believability. “There were definitely a few moments like that, yes,” he notes regarding whether he cut anything for being too over-the-top. “I never removed them because they were unbelievable. The reason some things did not make it into the final script was simply because they were a little too private. Some memories are better kept for yourself, even when you are telling an honest story.” Even the title itself—a symbol rooted in a specific memory—is a secret he guards, insisting that if you want to know the meaning, you have to show up.

No matter how selective, the power of his honesty was made clear during the show’s first run. Maddigan recalls a moment on the second night when a stranger, who had lost his own father, approached him.

“Some memories are better kept for yourself, even when you are telling an honest story.”

“Someone from my old school came along and brought a friend with him. I had no idea that this friend had lost his dad two years earlier. When the show finished, he came straight up to me and hugged me like we had known each other our whole lives, even though we had never met. He just said, ‘that was the first time in years I didn’t feel alone.’ That moment stopped me in my tracks. It was the first time I understood the real impact the story could have, and it made me realise that the fifteen year old version of me on stage was connecting with people in ways I never expected.”

There are future projects lined up for Ollie—in the works but under wraps “Keep your eyes peeled — I think people will be pleasantly surprised when things start to be announced,” but for now, his focus is on the Southwark stage, and the hope that younger audiences might see the value in dropping the performance of teenage bravado.

“What I really hope is that younger audiences see that the more he drops the act and lets people see who he actually is, the more respect he earns. If they can connect with that, maybe it encourages them to take off their own masks a little too.”

Featured Image: The Olive Boy_Credit Origin Studio