The Olive Boy is produced by Free Run Productions.
When Ollie Maddigan was fifteen, his mother died — a loss that sits at the heart of The Olive Boy, his one man show based on his own story. Knowing that the piece is written and performed by Ollie himself adds a layer of intimacy to the experience; you’re not just watching a character process grief, you’re watching the person who lived it r visit those memories in real time. Ollie has already built a reputation as a talented writer performer with a knack for blending humour and vulnerability, and this show, which has already travelled through the Edinburgh Fringe and earned him an (Off West End) Offie Award, demonstrates why.
Ollie has talent in abundance:105 minutes of his dynamic, sometimes frenzied performance, taking on different characters throughout but essentially showing his vulnerability is incredible to absorb.
The Olive Boy title comes from a nickname his mother gave him at birth — he was apparently a shade of green when he arrived, and she jokingly called him her “Olive Boy.” It’s a small, affectionate detail, but in the context of the show it becomes something heavier: a symbol of the things he’s been carrying since childhood, and the things he’s still trying to swallow years after her death. That metaphor threads through the performance, sometimes lightly, sometimes with real emotional weight.
The early part of the show leans heavily into teenage humour — the kind of crude, chaotic energy that will be instantly recognisable to anyone who grew up around boys of that age. I’ll admit I wasn’t sure at first whether it was going to be for me. A few audience members were laughing loudly at jokes that didn’t land for me at all. But gradually, almost without you noticing, the tone shifts. The humour doesn’t disappear, but it becomes a gateway into something more complex and deeper.
Ollie takes us through the awkwardness of adolescence — the social hierarchies, the obsession with girls, the desperate attempts to appear normal when nothing in your life feels normal at all. There are shades of The Inbetweeners and Kevin and Perry, but with a darker undercurrent and a desperate need to fit in. After his mother’s death, Ollie is sent to live with his estranged father and thrown into a new school where he clings to the distractions of teenage life: the naïve hope that a first girlfriend might fix everything. It’s funny, but it’s also painfully recognisable.
One of the most striking elements is “The Voice,” a recorded therapist played by Ronni Ancona. She’s never seen, only heard — distant, muffled, slightly awkward — which mirrors the way teenage boys often experience therapy: something happening at them rather than with them. Those moments highlight the silence around boys expressing grief, and the way young men are often expected to carry on as if nothing has happened.
As the story unfolds, so does the emotional impact. What begins as a string of teenage mishaps deepens into a portrait of a boy trying to hold himself together while the adults around him don’t quite know how to help. By the end, several people in the audience were wiping away tears, and I found myself unexpectedly moved. I felt a great deal of sympathy for Ollie— not just the character he portrays, but the young man who lived through this.
The Olive Boy has grown over several years, from its early development as a sellout Edinburgh run in 2022 and a short UK tour in 2024. This new season at Southwark Playhouse feels like a natural next step. Under Scott Le Crass’s direction, the show retains its rawness while gaining clarity and shape. It’s honest, messy, funny, and deeply human — a reminder that grief doesn’t vanish, it simply reshapes itself as we grow.
I highly recommend The Olive Boy and I can see a successful future for Ollie Maddigan in writing and performing. This is your chance to see him before the big time comes calling.
Runs from 14th January - 31st January 2026
Age Guidance: 14+
Warning: Strobe Lighting
https://southwarkplayhouse.co.uk/productions/the-olive-boy/
Reviewer: Penny Curran
On: 16th January
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