It’s tough being fifteen, right?
Imagine what happens when your raging teenage hormones are further complicated by the sudden death of your mother and the reappearance of your absent father.
Based on Ollie Maddigan’s real life story, the olive boy is forced to change schools and move in with a man he barely knows. In a hopeless attempt to stay sane, he decides that the only way to move forward is to pursue the chances of finally getting a real girlfriend.
Like most things in his life, it does not go to plan…
Photo by Origin Studio
First staged at the Hope Theatre in 2021, the show quickly gained attention at the Camden Fringe due to its inspiring message. After a sell-out Edinburgh Fringe run and a 6-week national tour, The Olive Boy launches at Southwark Playhouse Borough with this hilarious yet heartfelt comedy based on real life experience.
We caught up with Ollie Maddigan to learn more about the piece.
The Olive Boy is deeply personal, rooted in your own life experiences. Could you share what inspired you to transform such a challenging time into a narrative for the stage?
Absolutely. For a long time I kept that period of my life locked away because it felt too heavy and too raw. Over time I realised that the grief I was carrying was not something I needed to hide from. It was a story. And not just my story, but one that many people silently live through. What pushed me to bring it to the stage was the hope that by telling the truth, the real and sometimes uncomfortable truth, someone in the audience might feel less alone. If even one person recognises a part of their own experience and feels understood, then something painful has been turned into something meaningful.
You explore some intense themes in the play, like loss and the struggles of adolescence. How did you approach writing about your mother’s death and the tumultuous relationship with your father while keeping the tone both humorous and heartfelt?
With complete and utter truth. I always say that tragedy is simply humour with time. Teenagers are funny. They are clueless at times, but they are funny. When you go through something as huge as losing your mum, the pain can feel impossible to carry, but you do not suddenly stop being a teenager. You are still caught between growing up and messing up, still finding the world confusing and ridiculous even in the middle of heartbreak. That mix of raw grief and awkward teenage life is exactly what I wanted to capture. I also think, now, this is why the show works so well. Because it is tragic, but still very funny throughout.
With complete and utter truth. I always say that tragedy is simply humour with time. Teenagers are funny. They are clueless at times, but they are funny. When you go through something as huge as losing your mum, the pain can feel impossible to carry, but you do not suddenly stop being a teenager. You are still caught between growing up and messing up, still finding the world confusing and ridiculous even in the middle of heartbreak. That mix of raw grief and awkward teenage life is exactly what I wanted to capture. I also think, now, this is why the show works so well. Because it is tragic, but still very funny throughout.
The blend of comedy and serious subject matter can be tricky. How do you balance these elements in your writing, and what techniques do you employ to ensure the humour resonates even amidst the more poignant moments?
When it’s done well, humour can actually deepen the tragedy. There are several moments in the show where a joke lands as genuinely funny at first, but once the audience sees the full context later on, that same joke becomes heartbreaking. A lot of people have told me that on a second watch, the comedic moments feel almost tragic because they understand the bigger picture.
When it’s done well, humour can actually deepen the tragedy. There are several moments in the show where a joke lands as genuinely funny at first, but once the audience sees the full context later on, that same joke becomes heartbreaking. A lot of people have told me that on a second watch, the comedic moments feel almost tragic because they understand the bigger picture.
For me, it’s about making sure the audience never disconnects. If everything is unrelentingly intense, they’ll naturally pull away, so you have to counterbalance the darkness with light. It is theatre, after all — and being truthful means acknowledging that even in the bleakest moments, things can still be funny.
The Olive Boy first premiered at the Hope Theatre in 2021 and has seen incredible success since then. How did the positive reception at the Camden Fringe influence your decision to take the show to the Edinburgh Fringe Festival?
I always knew that going to Edinburgh was a dream of mine. I just needed to find the right show to take there. After the run at the Hope in 2021, I knew I had found it with The Olive Boy. The real challenge was finding the funding to actually get there.
I always knew that going to Edinburgh was a dream of mine. I just needed to find the right show to take there. After the run at the Hope in 2021, I knew I had found it with The Olive Boy. The real challenge was finding the funding to actually get there.
After a sold-out run in Edinburgh and a national tour, what made you choose Southwark Playhouse Borough for the next chapter of The Olive Boy?
There was never a clear decision. I just knew that after Edinburgh my next goal was to bring the show to the Southwark Playhouse. Since I am not a producer, I had no idea how to make that happen. Luckily, after the success of the tour, everything began to fall into place on its own. It feels exciting to give The Olive Boy a home for a few weeks, a place where people can discover it, talk about it, and hopefully bring others who might find real meaning in the story. It is a chance for the piece to reach the people who need it.
There was never a clear decision. I just knew that after Edinburgh my next goal was to bring the show to the Southwark Playhouse. Since I am not a producer, I had no idea how to make that happen. Luckily, after the success of the tour, everything began to fall into place on its own. It feels exciting to give The Olive Boy a home for a few weeks, a place where people can discover it, talk about it, and hopefully bring others who might find real meaning in the story. It is a chance for the piece to reach the people who need it.
Have you had to prepare any differently ahead of this London run?
Yes, a lot. Since I am co-producing this run, which I did not do during the tour, there are many more challenges in front of me. I am constantly thinking about The Olive Boy and how to make this run the strongest it has ever been. At this point I truly believe that will happen. I am doing everything I can to make the show accessible to charities and colleges. Productions like this are rarely shown to real fifteen-year-old boys, and I think it is important that they get the chance to see it.
Yes, a lot. Since I am co-producing this run, which I did not do during the tour, there are many more challenges in front of me. I am constantly thinking about The Olive Boy and how to make this run the strongest it has ever been. At this point I truly believe that will happen. I am doing everything I can to make the show accessible to charities and colleges. Productions like this are rarely shown to real fifteen-year-old boys, and I think it is important that they get the chance to see it.
On the performing side, I feel happy to be at home. This will be the first run since 2021 where I get to sleep in my own bed after the show, and I honestly cannot wait for that.
How do you reflect on the journey of the show so far and what do you hope for it going forward?
I look back on the journey of the show with a huge amount of gratitude. It started as something incredibly personal, something I was not even sure I would ever share, and it has slowly grown into a piece that has touched people in ways I never expected. Each stage of the journey, from the first small run to the tour and now this new chapter, has taught me something new about the story and about myself.
I look back on the journey of the show with a huge amount of gratitude. It started as something incredibly personal, something I was not even sure I would ever share, and it has slowly grown into a piece that has touched people in ways I never expected. Each stage of the journey, from the first small run to the tour and now this new chapter, has taught me something new about the story and about myself.
Looking forward, I simply hope it continues to reach the people who need it. If it can keep opening conversations, offering comfort, or helping someone feel seen, then that is all I could ever want. I would love for the show to keep growing, to keep finding new audiences, and to continue having a life beyond me. As long as it is helping people connect with their own experiences, the journey will always feel worthwhile.
For someone yet to see the show, how would you describe the experience in just a few words?
The Olive Boy is a bit like a one man show starring Jay from The Inbetweeners if we finally got to understand why he lies so much. It has that same frantic energy and awkward teenage bravado, but underneath it all there is a real heart and a real reason for the performance he puts on for the world.
The Olive Boy is a bit like a one man show starring Jay from The Inbetweeners if we finally got to understand why he lies so much. It has that same frantic energy and awkward teenage bravado, but underneath it all there is a real heart and a real reason for the performance he puts on for the world.
What was the first piece of theatre you remember having a big impact on you?
The Phantom of the Opera. I would tell you why, but I already explained it in the show. So if you want to know the full story, you will have to come and see it.
The Phantom of the Opera. I would tell you why, but I already explained it in the show. So if you want to know the full story, you will have to come and see it.
What keeps you inspired?
Coffee and mum.
Coffee and mum.
The premise of a boy navigating teenage challenges while grappling with grief is intriguing. What do you hope the audience takes away from Ollie's journey, especially during moments when things don’t go as planned?
You are never as alone as you feel. Grief has a way of convincing you that you are the only person carrying that weight, but the truth is that every person you pass has faced their own version of it. Grief is love that has nowhere to go, and learning to speak about it is one of the bravest things you can do. When you let yourself be honest about your hurt, people respond with compassion. They always do.
You are never as alone as you feel. Grief has a way of convincing you that you are the only person carrying that weight, but the truth is that every person you pass has faced their own version of it. Grief is love that has nowhere to go, and learning to speak about it is one of the bravest things you can do. When you let yourself be honest about your hurt, people respond with compassion. They always do.
If any part of your life mirrors the story in the show, or if you have lived through something that still sits quietly inside you, I would love you to come along. I always stay in the bar afterwards, and anyone is free to talk to me, even if it is only for a minute. You might be surprised by how much lighter things feel when you say them out loud. We are all human, we are all trying, and the moment we allow ourselves to speak to one another with real openness, the world becomes a kinder place.
The Olive Boy plays at Southwark Playhouse Borough in The Little from 14th to 31st January 2026. Tickets are available from https://southwarkplayhouse.co.uk/productions/the-olive-boy/
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