Ollie Maddigan (The Olive Boy)

When writer and performer Ollie Maddigan was fifteen, his mum died and he was the one who found her. The Olive Boy explores how he attempted to make sense of life at a time where everything was falling apart and yet he was expected to carry on as normal. After successful runs at the Camden Fringe and Edinburgh Fringe, as well as winning an Offie award during its UK tour, The Olive Boy is set to have its first dedicated London Season at the Southwark Playhouse this January, which is directed by Scott Le Crass.

We took the opportunity to speak with Ollie to tell us more.

Q) The Olive Boy is based on your own experiences of losing your mum at fifteen. What finally made you feel ready to share it on stage?

I think what finally made me ready was realising that keeping it to myself was only holding the story back. I wanted to tell the truth about that period of my life, the grief, the awkwardness of being a teenager, and the moments that were both painful and absurd. Once I accepted that the story belonged on stage more than it belonged in my head, I knew it was time. It felt like a way to honour my mum and also connect with anyone who has felt alone in their grief.

Q) Was there a specific moment when you realised that humour could be part of telling a story about grief?

I think it came naturally as I wrote. Even in the darkest moments of losing my mum, I was still fifteen, still a teenager, still ridiculous at times. Life never lets you stop being a teenager just because it’s painful. I realised that humour could be a bridge — a way for people to engage with grief without it being overwhelming. Comedy allowed the truth of the pain to come through more honestly, not less.

Q) How much of The Olive Boy is drawn directly from your real life, and how much did you find yourself reshaping or fictionalising for the stage?

A lot of it is drawn directly from my life, from the feelings, the memories, the small truths of being fifteen and losing someone so central to you. But for the stage, I had to reshape some moments — compressing time, combining people, exaggerating certain scenes — to make them work dramatically. The core, though, the heart of the story, is entirely real. Everything else is just the way a story needs to breathe in a theatre.

Q) The title comes from a nickname your mum gave you — can you tell us more about what that name means to you now?

The nickname is a constant connection to her, a reminder that even though she is gone, the love and the little private jokes we shared are still very much alive. It’s a name that grounds me, that reminds me who I am and where I come from.

Q) The play explores the silence around boys expressing grief. How did your own teenage experience of that silence inform the show?

I was painfully aware that boys are rarely taught to speak about grief. At fifteen, I didn’t know how to say it, and I certainly didn’t feel it was acceptable to show it. That silence shaped everything in the show — the awkwardness, the deflection with humour, the masks we put on. I wanted to show that even when boys seem like they are managing or hiding, there is a depth of feeling underneath, and that it’s okay to express it.

Q) You perform the piece yourself — how does it feel to re-live such personal memories every night on stage?

It is intense. Some nights it hits harder than others, and sometimes I feel like I am back fifteen years old in an instant. But it’s also a privilege. Performing the story allows me to process my own grief and to share it with others in a way that creates connection. The audience’s reactions remind me that my experiences are not mine alone, and that brings a sense of purpose to every performance.

Q) You’ve said before that grief isn’t a burden, but “the price for love.” How has your understanding of grief changed since writing the play?

I think I understand now that grief is less about pain alone and more about love that remains. Writing and performing the play has shown me that grief changes shape over time. It can be sharp, it can be quiet, it can even become part of joy. It is not something to hide from or “get over.” It is proof of love, and learning to carry it is a lifelong process.

Q) You first staged The Olive Boy at the Camden Fringe and then at Edinburgh before this London run. How has the show evolved since those early performances?

The show has grown in confidence and clarity. Early performances were very raw, and I was still finding my voice and the rhythm of telling the story. Touring it and performing it multiple times has given me the chance to see what lands with audiences, what moments need more space, and what lines carry the most weight. It has also helped me appreciate how universal the story is — audiences react to it in ways I never could have imagined back in Camden.

Q) What do you hope young people who see the show — particularly young men — might take away from it?

I hope they see that it is okay to feel, to be vulnerable, and to express themselves. I hope they realise that grief does not make you weak, and that humour and sadness can exist together. Most of all, I hope it encourages them to take off their masks and be honest with themselves and with others. If even one young person leaves the theatre feeling seen or understood, then the show has done its job.

The Olive Boy will be performing at Southwark Playhouse from 14th January to 31st January 2026.

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Photography by Origin Studio and Adam Jeffreys