After a short UK tour last year, Ollie Maddigan’s The Olive Boy will go to Southwark Playhouse for a London run next year.
First developed at Camden Fringe 2021, this deeply personal play will run at Southwark Playhouse Borough between 14-31 January 2026. The production is written and performed by Ollie Maddigan, directed by Scott Le Crass, with additional recorded dialogue by Ronni Ancona.
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. The show, written and performed by Ollie himself, mixes sharp humor with raw honesty to show what grief really feels like – sometimes messy, sometimes funny and always quietly devastating.
The play begins with a series of missteps and small heartbreaks that evolve into something deeper: an honest, darkly comic look at the absurdity of loss, and how adolescence turns grief into achievement. Move between comedy and confession, The Olive Boy captures the contradictions of growing up while falling apart—and eventually learns 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 usual distractions of adolescence – girls, quirky streaks, social status and the naïve hope that a first girlfriend can 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—mirroring the uncomfortable distance he felt in teenage counseling and the broader silence surrounding boys expressing grief.
The title Olive Boy comes from a nickname Ollie’s mother gave him at birth, a small and affectionate joke that has taken on new weight since her death. The olive also becomes a symbol of everything he 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 who pretends to be fine, caught between the silence expected of young men and the interrupting conversation of therapy. Over time, what was once unmanageable began to settle into everyday life. The grief didn’t go away, but reshaped itself – becoming part of the person he was still learning to be.
Firmly rooted in Ollie’s own life, The Olive Boy speaks to something further. Grief, adolescence and the search for words around pain are experiences that touch us all. The play resonates with anyone who has suffered loss—or who has ever tried to hold it together when the world expected them to be fine. Anchored by humor 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.
Tickets to The Olive Boy can be found here.
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