Interview with Ollie Maddigan on theatre play,
The Olive Boy

Interview by Louise Cannon

Showing at Southwark Playhouse Borough in January 2026, Olive Boy is award winning (Offie Award) and has previously had successful runs at both Camden and Edinburgh Fringe Festivals. I have had the great opportunity to interview Ollie Maddigan about his play, Olive Boy, performed and written about him, with timely voiceovers performed by impressionist/comedian/actress, Ronnie Ancona. We delve into losing his mum at 15, counselling, making sense of the world and more… I thank Ollie for his courage, willingness and honesty in answering my questions on such a sensitive topic as I recognise it’s one thing to perform it, but quite another to be interviewed about it.
Here’s a bit about the play and then there’s the interview and details of how you can see the play.

“When Ollie was fifteen, his mum died, and he was the one who found her. The Olive Boy explores his attempt to make sense of life at a time when everything was falling apart, yet he was expected to carry on as normal. It looks at what it means to grow up with that kind of loss, especially as a teenage boy navigating school, friends, first relationships and the pressure to keep quiet about how you’re actually feeling. 

A therapist’s recorded voice, played by Ronni Ancona, runs through the piece, reflecting the distance he felt in counselling at the time and the wider silence around boys expressing grief and all the emotions that come with it.”

Firstly, congratulations on having The Olive Boy transfer from Camden Fringe to the Edinburgh Fringe Festival, where it sold out and winning an Offie Award to having a dedicated London season. What does that feel like and how does this inspire you to keep going?

Simply put, it feels great. You never imagine, when you’re first creating a show, that it could grow to this level, so I feel completely privileged. Watching The Olive Boy move from a tiny Camden Fringe run to Edinburgh, to a national tour, to an Offie Award, and now to a London season has genuinely been one of the highlights of my career. It’s been overwhelming in the best way. In terms of what inspires me to keep going, I think you know instinctively when something has reached its end and when it hasn’t. For a long time, I felt there was still more to do with this show and more people it could reach. That said, the run at Southwark might be the final chapter for The Olive Boy and if it is, it feels like the right place to end it.

 

2. Secondly, sorry to hear about the loss of your mum at such a tender age.

The Olive Boy is about exploring a 15-year-old Ollie finding mum dead and trying to make sense of the world. What impact did that have on you at 15 years old and the adult you now?

 

Losing my mum at 15 changed everything. At that age you don’t really have the emotional language to understand something so sudden, so you just try to keep moving and hope you’ll catch up with yourself later. It forced me to grow up quickly, but it also left a lot of confusion that I didn’t unpack until adulthood. As an adult, I can see how much that moment shaped my humour, my outlook, and the way I connect with people. The show has been a way of finally giving that younger version of myself some space to be heard, and in doing so, it has allowed me to understand the adult I became.

 

3. What did it feel like looking back to when you were 15 years old and what did you gain from this as that younger you tried to make sense of a world without mum physically in it anymore?

 

Looking back at myself at 15, I mostly feel a mixture of compassion and frustration. I can see how hard I was trying to make sense of something that didn’t make any sense. When you lose a parent that young, you’re suddenly pushed into a world that feels far too adult, but you’re still very much a child trying to keep up. What I gained from revisiting that younger version of me was perspective. I realised how much he was carrying without the tools to process it, and how he used humour and distraction to survive it. Writing the show allowed me to acknowledge that, rather than judge it. In a way, it gave that younger me the space and understanding he never had at the time.

 

 

4. Therapy is still a bit taboo for some people, but it was more so for boys at a certain time, and a bit for even girls at a certain time too, but what was it like for you to attend counselling? You talk about reflecting the distance you felt, what effect did that have and would you ever consider counselling or recommend it to people now therapy is slowly opening up to wider ranges of people?

 

Counselling was a complicated experience for me at that age. It wasn’t something boys really talked about, and I remember feeling quite distanced from it, almost like I was watching myself go through the motions rather than actually opening up. I didn’t have the vocabulary to express what I was feeling, so it felt easier to stay on the surface.

That distance definitely stayed with me for a long time. It meant a lot of emotions got stored rather than processed, and I’m only now, as an adult, realising how much that shaped me.

Would I consider counselling now or recommend it? Absolutely. I think the stigma is slowly shifting, and people are starting to see therapy for what it really is: a space to understand yourself better. I wish I’d had the tools back then to make the most of it, but I can recognise now how valuable it can be, especially for young people who are trying to navigate grief or upheaval.

 

5. After your mum died, there was a pressure felt to keep quiet about your emotions. What was living up to that pressure like?

 

There was definitely a pressure to keep quiet about what I was feeling after my mum died, and living up to that was exhausting in ways I didn’t understand at the time. When you’re young, you think staying silent is the same as staying strong, so you push everything down and hope it will sort itself out.

Looking back, that pressure created a kind of emotional numbness. I became very good at performing “being fine,” even when I wasn’t. It took years to recognise how much energy went into holding everything in, and how isolating that can be. The show has helped me confront that silence and acknowledge the cost of it.

 

6. When trying to make sense of this world you were living in without your mum, what conclusions did you come to between then and now?

 

 

When I was 15, I didn’t come to many real conclusions at all. I think that’s the point: you try to make sense of a world that suddenly doesn’t make sense anymore, and most of what you land on is survival rather than understanding. At the time, my conclusion was simply to keep going, keep my head down, and hope things would eventually feel normal again.

Looking back now, the adult version of me can see that there is no neat conclusion to losing someone so central. What you find instead is acceptance. You learn that grief doesn’t disappear; it just changes shape as you grow. You learn that you can carry loss and still build a life around it. And you realise that the world without my mum physically in it is still a world she shaped through the memories, the humour, the resilience, and the perspective she left behind.

 

7. Ronnie Ancona plays your counsellor in a recording. What was that like to have her on-board and be on stage yourself, knowing it was just her voice that carried through?

 

I mean, come on — it’s Ronni Ancona. Who better to play a character called “The Voice” than someone famous for her vocal impressions?

For me as a performer, it was a strange but exciting dynamic. You’re on stage responding to someone who isn’t physically there, but because it’s Ronnie, the performance feels alive. Her delivery is so precise and nuanced that it gives you something real to play off. It elevated the scenes and added a layer to the show that audiences always respond to.

 

8. How did you inject humour into what feels heartfelt and such a personal play?

 

Teenage boys are funny. No matter what they’re going through, they’re crude, ridiculous, and absolutely convinced they know everything. I wanted to show that when you’re grieving as a teenager, you don’t suddenly stop being a teenager. You can be dealing with the biggest loss of your life and still be just as focused on trying to get past the child-blocker on the computer.

That contrast felt important to capture – the messy, contradictory reality of being fifteen and grieving, but still undeniably a teenage boy.

 

9. What do you get personally from telling your story on stage in-front of a live audience?

 

There’s something grounding about standing in front of a room full of people and saying, “This happened, and it shaped me,” and feeling them meet you with empathy rather than judgement. It’s not about reliving the past; it’s about making sense of it in real time. When audiences laugh at the stupid teenage moments or fall silent during the heavier ones, it reminds me that grief is universal, and that there’s value in being open about it.

 

10. What do you hope the audience will get out of your show, Olive Boy?

What I hope audiences take away from The Olive Boy is a sense of recognition. Whether they’ve experienced grief themselves or not, I want them to connect with the idea that growing up is messy, complicated, and never as straightforward as you expect it to be. If people leave feeling seen, or feeling like their own story makes a bit more sense, then the show has done its job. Above all, I want people to feel that, even in difficult chapters, there can still be humour, connection, and a way forward.

11. Where can people follow you/your play?

 

O.maddigan on Instagram for me and Theoliveboyshow on Instagram for the show!

The Olive Boy will be performing at Southwark Playhouse from 14 January to 31 January 2026. Tickets and information: https://southwarkplayhouse.co.uk/productions/the-olive-boy/