Ollie Maddigan’s The Olive Boy comes to Southwark Playhouse Borough

A darkly comic coming-of-age story about grief, boyhood and learning to live with love and its absence.

When Ollie Maddigan was fifteen, his mother died. The Olive Boy is based on a true story, one that he has been trying to tell ever since. Written and performed by Maddigan himself, the show blends sharp humour with raw honesty to show how grief really feels - sometimes messy, sometimes funny and always quietly devastating.

In this deeply personal play, The Olive Boy begins with a series of missteps and small heartbreaks that unfold into something deeper: an honest, darkly comic look at the absurdity of loss, and the way adolescence turns grief into performance. Moving between comedy and confession, The Olive Boy captures the contradictions of growing up while falling apart - and learning, eventually, that love and grief are two sides of the same story.

After his mother’s death, Ollie is sent to live with his estranged father. At a new school, surrounded by strangers, he clings to the ordinary distractions of adolescence - girls, snap streaks, social status and the naïve hope that a first girlfriend might make life feel normal again. “The Voice” (played by Ronni Ancona) is the recorded presence of a therapist - heard throughout the play but never seen - reflecting the awkward distance he felt in teenage counselling and the wider silence around boys expressing grief.

The title Olive Boy comes from a nickname Ollie’s mum gave him at birth, a small and affectionate joke that has taken on a new weight since her death. The olive also becomes a symbol for everything Maddigan tries to swallow since her death - the bitterness of loss, the strangeness of growing up and the awkward attempts to get through the next bite of teenage life. At fifteen, he carries the bravado of a boy pretending he’s fine, caught between the silences expected of young men and the halting conversations of therapy. Over time, what was once unmanageable began to settle into the everyday. Grief did not disappear, but reshaped itself - becoming part of the person he is still learning to be.

“This grief that I carry isn't a burden… It’s the price for love. And it’s worth it.” 

Though rooted in Maddigan’s own life, The Olive Boy speaks to something wider. Grief, adolescence and the search for words around pain are experiences that touch us all. The play resonates with anyone who has carried loss - or who has ever tried to hold themselves together when the world expected them to be fine. Anchored by humour and honesty, it is both an intimate portrait of personal loss and a broader reflection on what it means to grow up in the aftermath of grief, showing how we all learn to live with love and its absence.

First developed at the Camden Fringe in 2021, The Olive Boy has grown over several years. It went on to a sell-out run at the Edinburgh Festival Fringe in 2022, followed by a short UK tour in 2024 that earned an Offie Award for Creation. This new season at Southwark Playhouse marks the production’s first dedicated London run.

The production is written and performed by Ollie Maddigan, directed by Scott Le Crass, with additional recorded dialogue by Ronni Ancona.

Listings information:Venue: Southwark Playhouse Borough, 77-85 Newington Causeway, London SE1 6BDRun: 14th January - 31st January 2026https://southwarkplayhouse.co.uk/productions/the-olive-boy/