The Olive Boy
31 January 2026
Southwark Playhouse Borough
3.0 out of 5.0 stars
The Olive Boy concluded its short two and a half week run at the Southwark Playhouse Borough this past Saturday, and I managed to sneak in a visit on the last day of the run. Based on Ollie Maddigan’s own teenage life, the show revolves around a 15 year old boy who recently had to uproot his entire life. After the unexpected death of his mother, he is forced to move to the big city to live with his father, whom he barely knows. A new school, new friends, new city, and a whole lot of grief to work through, it’s a teenage drama cloaked in the bravado of a young boy trying to redefine himself while making sense of his new life.
Presented mostly as storytelling towards the audience, Maddigan inhabits the role of a braggadocios teen boy effortlessly, slinking in and doing a leisurely double-take before springing into action. Slipping into the roles of his peers with brilliantly funny characterisations of well-known adolescent stereotypes, he breezes through the narrative, weaving the more serious moments between hilarious misadventures in making new friends and trying to find his first girlfriend.
The show runs just over an hour without an interval, wrapping its audience into the story without interruption. There are moments of strong misogyny woven into the boasting pretension of a teenage boy wanting to seem cool in front of a new group of peers, softened by the more emotional undertone of heavy grief and confusion. It feels like a very realistic portrayal of youth, and a very personal journey of grief, lightened by a heavy dose of humour and a dollop of teenage drama.
The Olive Boy is an interesting semi-autobiographical piece, full of emotion and energy, blending the high stakes of teenage reputation building with the deep sadness and anger of going through the loss of a parent. There are very touching moments in this show, especially towards the end, and a good dose of humour throughout.
