You Can’t Go Wrong with Oliver: Jamaican Comedy Comes to Bermuda
Get ready, Bermuda! The stage is set for a night of laughter and entertainment as legendary Jamaican comedian Oliver Samuels takes the lead in the play Lucky Money. This highly anticipated performance will light up the Ruth Seaton James Auditorium at CedarBridge Academy in Devonshire on February 28 and March 1, starting at 7 PM.
At 71 years young, Oliver Samuels, affectionately known as the King of Jamaican Comedy, is no stranger to the spotlight. With over 70 plays under his belt and appearances in films like Great Moments in Aviation and Almost Heaven, his journey from a young boy in St. Mary’s, Jamaica, to a celebrated actor is nothing short of inspiring.
“I wanted to be a teacher until acting turned my head,” Oliver shared with a chuckle. His love for performance ignited at the tender age of eight when he watched a Tarzan movie. “I was so caught up in it that I worried about how we were going to get home through all the mud when it started to rain in the film!” he recalled, laughing at his younger self’s innocence. “I was captivated by that magic. I wanted to be a part of it.”
Lucky Money is a vibrant piece of theatre that has been touring since May of last year. “Wherever we play, the audience just gets so involved in the whole thing,” Oliver said. “We are enjoying it. The reception has been absolutely terrific.”
The play, directed by Pablo Hoilett, tells the story of two men: Walter Nelson, an affluent and educated character played by Tesfa Edwards, and Anton DeSouza, portrayed by Oliver himself, who is streetwise and clever. When Walter tries to swindle Anton after they win the lottery, Anton has a few tricks up his sleeve. “Justice prevails in the end,” Hoilett assures, emphasizing that Lucky Money is a clean, fast-paced comedy suitable for the whole family.
Wendell “Shine” Hayward, the mastermind behind bringing this production to Bermuda, has a long-standing friendship with Hoilett. “With Oliver Samuels as the lead actor and Pablo Hoilett as the director, you could not go wrong,” Hayward said, expressing his excitement for the show.
The play has roots in Brazilian theatre, originally written in Portuguese in the 1960s. Hoilett reworked it for a Caribbean audience, ensuring it resonates with local culture. “We had to make it relevant for our culture,” he explained, highlighting the importance of adapting stories for different audiences.
Joining Oliver and Tesfa on stage is the talented Karen Harriott, a well-known figure in Jamaican theatre. The vibrant theatre scene in Jamaica is alive and well, with multiple productions running simultaneously. “Lucky Money is one of the most successful ones,” Hoilett noted, as they continue to perform for the Caribbean diaspora across various locations, including Canada and the United States.
As the curtain rises in Bermuda, Hayward is eager to experience the full performance for the first time. “I’ve only seen snippets of Lucky Money. I want to enjoy it in its entirety when it hits Bermuda,” he said, reflecting the anticipation surrounding the event.
Tickets for this comedic gem are available online, with regular tickets priced at $80 and patron tickets at $125. Will you be part of the laughter that fills the auditorium? Don’t miss your chance to see Oliver Samuels shine on stage in Lucky Money!

