Interview with Ollie Maddigan

In this interview, I had the great pleasure of doing an interview with Ollie Maddigan, about the upcoming production ‘The Olive Boy’. He has shared insights into what audiences can expect from this show, as well as the inspiration and hard work behind bringing this show to life.

The Olive Boy is rooted in your own experience of grief as a teenager. What made now the right moment to tell this story publicly?

For years I avoided thinking about that time because it felt too overwhelming and I genuinely didn’t know how to sit with it. Eventually I realised the loss I’d been carrying didn’t need to stay hidden. It was part of my life, and strangely, it connected me to far more people than I ever expected. And like every writer gets told at some point, you should write what you know. At the time I began creating this piece, grief was the thing I understood best.

Writing about something so personal can be daunting. What was the emotional journey of turning lived trauma into scripted storytelling?

I went into writing the play with this strange pressure that I was telling a story only I knew. And in a way, that’s true for every playwright: you’re the only one who fully understands the world you’re building until you start putting it on the page. But what surprised me was how much I didn’t know about myself until I started creating the character. There were memories, habits, little emotional reflexes I hadn’t clocked in years that came spilling out once I began writing in his voice.

Going back to that time in my life was tough, there were moments that felt like reopening a box I’d taped shut for a reason. But it was also unexpectedly funny. I kept remembering how young and spectacularly clueless I was, walking around convinced I had life completely sussed when I didn’t have a clue. That mix of pain and humour, revisiting all the things I got wrong while trying to make sense of the things that hurt, ended up shaping the play more than I expected. It became less about retelling an old memory and more about understanding who I was then, and who I’ve grown into now.

The show began at Camden Fringe and has evolved significantly since. How has the piece grown or shifted over the last few years?

In a lot of ways, the show really hasn’t changed. I’m still using the same music, the same script, and the same non-existent set. It’s still just me and a chair. And honestly, I think that’s part of what makes The Olive Boy feel so intimate. The simplicity forces the audience to lean in. It feels like the character is speaking directly to you.

People sometimes expect a show to evolve by getting bigger- more lights, more set pieces, more “stuff.” But for this story, that would actually pull focus away from what it truly is: a boy sharing his story. If it suddenly became a huge spectacle with moving scenery and flashy transitions, the heart of it would get lost.

So the evolution hasn’t been about adding things. It’s been about trusting the simplicity. Letting the story stand on its own.

You mix dark comedy with deeply vulnerable material. How did you find the balance between humour and honesty?

The truth is funny. When your mum dies as a teenager, you don’t suddenly stop being a teenager. And that was a big part of the show I wanted to capture. I wanted the audience to feel like they really are just watching a teenage boy talk at them for 75 minutes straight. And if we know anything about teenage boys, it’s that they’re rude, crude, incredibly immature, and half the time they’re saying things before they’ve even thought them through. With a character like that at the centre, the humour naturally comes out. It never takes away from the sorrow,  it just shows the reality of what that age actually looks and sounds like, even in the middle of something devastating.

Adolescence, grief and masculinity collide throughout the story. What conversations do you hope this sparks?

Honestly, any conversation. The problem with grief isn’t the kind of conversations we have about it -  it’s that we barely have them at all. Grief is the one experience that connects every single one of us. It’s guaranteed. At some point in our lifetime, we’re all going to feel it. And yet, for something so universal, we don’t really talk about it. Not properly. If the show sparks even the smallest conversation between two people who wouldn’t normally bring it up, then that’s already a win.

The idea of grief reshaping itself over time is central to the play. How has your understanding of grief changed since you were fifteen?

At fifteen I thought grief was a single event - something horrific that hits you once and then slowly fades. But I’ve learned it’s more like a shape-shifter. It changes as you change. Some years it whispers, some years it shouts. I used to think healing meant “getting over it”. Now I know it means learning how to carry it without letting it define every part of you.

You’ve worked closely with director Scott Le Crass. How has his approach influenced the shape or tone of the piece?

Scott has an amazing ability to strip everything back to the emotional truth. He encouraged me to lean into the vulnerability rather than hide behind comedy or clever writing. He also brought a level of precision to the storytelling - he sees the beats I don’t even realise I’m playing. The show is braver, cleaner, and more grounded because of him.

From Edinburgh Fringe to Offie wins, the show has built a passionate following. How has the audience response surprised you?

The biggest surprise has been how many people come up to me afterwards wanting to share their own stories. It’s beautiful, and I always feel genuinely honoured to sit with someone after the show and hear their experience. You realise quickly that everyone carries something, and the show seems to give people permission to let a little of it out. I love hearing about their loved ones -  the names, the memories. There are people I now remember purely because of this show and the amazing audiences who’ve trusted me with their stories.

This is the first dedicated London run for The Olive Boy. What are you most excited—or nervous—about bringing it to Southwark Playhouse?

I’m absolutely sh*ting myself, to be honest. Southwark has always been the dream venue for this show, so now that it’s actually happening, I feel ridiculously grateful and a bit terrified. I can’t wait to perform it there, to finally share it in the space I always imagined for it. And, if I’m being completely honest, I’m also very excited about being able to go home afterwards and sleep in my own bed every night.

What’s been the biggest surprise in creating the show?

That it’s still going, honestly. It was meant to be three nights at the Camden Fringe, a little project for myself before I headed off to drama school. I never imagined it would grow into anything beyond that. And yet, years later, I’m still performing it. The fact that it’s now ending up at Southwark Playhouse, possibly for its final run, is something I genuinely never saw coming. It’s been the biggest and best surprise.

What’s the one thing you hope people carry with them when they leave the theatre?

That grief doesn’t make you strange or broken, it makes you human. If someone leaves feeling a little less alone in whatever they’re carrying, then the play has done its job.

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/