The Olive Boy explores the uneasy space between adolescence, grief and emotional immaturity

The phrase “boys will be boys” often gets used to excuse behaviour, rather than examine it. The Olive Boy explores that uneasy space between adolescence, grief and emotional immaturity.

First staged at the Hope Theatre in 2021, The Olive Boy has since enjoyed runs at both the Camden and Edinburgh Fringe Festivals and now arrives off-West End at Southwark Playhouse Borough, in The Little.

The play is structured as a series of flashbacks framed by a therapy session. The Olive Boy enters the stage, breaks the fourth wall and asks, “am I supposed to start?”, before leading us through the story of his teenage years.

At fourteen, he discovers his mother has died suddenly, with no warning or explanation. This loss, along with the reappearance of an father he barely knows, forces him to navigate grief alongside adolescence. Mixed in with a new school, new friends, girls, and an almost comical aversion to olives.

Written by and performed by Ollie Maddigan, The Olive Boy is clearly a deeply personal and cathartic exploration of grief. The writing feels honest and well-intentioned and there is no doubt that the material comes from a place of lived experience.

However, despite its sincerity, I struggled to find a distinctive hook that took the story beyond familiar territory. Many of the themes (teenage masculinity, emotional repression, loss, and confusion) have been explored extensively across theatre, television and film and this failed to really offer any new insight on the topic for me.

Performed as a one-man show in a black-box setting, the production relies almost entirely on the strength of the text and performance. While moments of lighting and strobe effects attempt to heighten the experience, they often feel distracting rather than illuminating, drawing attention away from the narrative rather than deepening it.

Ultimately, while I appreciate the honesty and vulnerability at the heart of The Olive Boy, it didn’t linger with me after leaving the theatre. By the time I reached the bus stop, the experience had already begun to fade, leaving behind only a faint, olive-tinted impression.

★★★

West End Wilma, January 2026