The history of the Cayman Drama Society tells of a theater company desperate to find permanent boards to tread. With roots in hotel play readings pre-1969, the society was assembled into an informal group in 1970, but it would take 20 more years before it could lay permanent claim to a theater base.

Finding a home

The Town Hall was the venue for the drama society’s first full play – “See How They Run” – in 1970 with Paul Dyson, and then Val Morgan, at the helm as director/producer, Peter Phillips enhancing lighting, and Dennis Smith and John Furze building the set.

Since this first, and extremely popular performance, the society organized formally and has gone through vast changes. Some 40 shows were presented over the next 14 years, most at the Town Hall, before the society went on the move in search of a more appropriate home. The notion of a purpose-built theater came with challenges, with the acquisition and then loss of a peppercorn lease on Racquet Club land for this purpose, and subsequent lease of Prospect Playhouse’s present land. But fundraising issues put a halt to any building.

Despite these challenges, the shows went on. St. Ignatius Catholic School Hall played host to “Toad of Toad Hall” and the society also used the Harquail Theatre workshop theater, followed by stints upstairs at the Lord Nelson Pub in Trafalgar Square as the Victory Theatre.

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Finally, with help of the subcommittee led by Penny and Peter Phillips, and a generous donation by Evelyn and Jack Andresen, construction began on the Prospect Playhouse. The grand opening in October 1990 was followed by a production of “Pirates Princess,” and the Cayman Drama Society had finally found its home.

‘Joseph and the Amazing Technicolor Dreamcoat,’ 2016

Society success

Since “See How They Run,” the drama society has produced and presented 201 musicals, dramas, pantomimes and comedies, with the theater producing, on average, four main shows – including one major musical (which is very expensive to stage because of copyrights and music) and one Christmas show per year. Not bad for a group that was once housed in a town hall, school auditorium and above a pub.

The Cayman Drama Society has become ingrained into the community of Cayman, offering locals a place to showcase their dramatic talents and a place for newcomers to meet people and develop life-long friendships.

Over the decades, numerous names have been associated with the society, with debuts from John Shield and Nick Press in the 1970s; Clive Munyard, Alan Hall and Tony Rowlands in the ‘80s; Roland Stacey, Consuelo Ebanks and Chris Mann in the ‘90s; and more recently, Dominic Wheaton, Jardel McIntosh, Sophie Gough and Melanie Ebanks. These are just a few of the seemingly endless roster of talented actors who have taken part in productions.

For Sheree Ebanks, the society’s chairwoman, 2006’s “Peter Pan” stands out as a memorable show as Peter Pan and the Darling children took to the skies. “It was quite a spectacle,” says Ebanks. “We utilized the services of a company in the U.S. who shipped all the flying equipment here, came and set it up and trained the operators. I was one of the backstage operators and I can tell you it was hard work getting those kids up in the ceiling.” Importing the flying gear and team to Cayman and sending them all back cost around $10,000 and was covered by one major sponsor.

“Little Shop of Horrors,” “Audrey II,” Colin Wilson’s “Magna Carta” and “Watler’s War” are also standout productions for Ebanks.

‘A Christmas Carol,’ 2006

How to get involved

Budding thespians can get involved with a variety of drama society shows each year by auditioning for roles. Those more aligned with behind-the-scenes work will be happy to know there are a full range of positions, even if you have no previous experience. Newcomers who are ultimately interested in acting are encouraged to become part of the crew first as it gives them a greater appreciation of what goes on backstage. Set-building, painting, lights and sound are all important jobs.

“We provide training and certification to those who want to do sound or lights,” says Ebanks. Backstage crew, stage managers, prop managers, costume designers and seamstresses – the list of options for people looking to get involved is quite extensive.

“For those who are not so inclined to work an actual show, we also need volunteers to help run our bar and box office during the shows. We are always looking for volunteers.

“If one cannot help personally, we also have a part of our website where people can donate to where we most need funds: training, our education fund and our building fund,” Ebanks says.

As for how much commitment is necessary, Ebanks says that is determined by what role is desired. While actors will have more read-throughs and rehearsals, backstage crew are required to attend six rehearsals two weeks before the show opens, followed by either three or four weeks of shows, with, primarily, three shows per week. Musicals typically run for four weeks with 12 to 14 shows. If you are volunteering for bar or front of house, a couple of hours per nights of your choice may be called for.

Rehearsals take place for “Peter Pan’, 2006

Those who are hesitant due to their lack of acting ability now have no excuse to be shy. In February, the drama society added a full-time operations and education officer to their team. Kirsty O’Sullivan ran the Edinburgh Acting School for the last six years and has now brought her passion for drama and acting education to Cayman to the benefit of new and seasoned actors of all ages. A range of acting classes are on offer for children of all ages, as well as monthly adult classes, including workshops and more specific training.

Getting involved with local theater means joining a vibrant and close-knit community.

“By joining a theater, you are able to meet people from all walks of life,” says Ebanks. “It is also very gratifying to be a part of a team that has had a great run – it is hard to explain the amazing energy and buzz during, and right after, a show. It is a great way to learn new skills – and acting skills are extremely valuable in every walk of life.”

“CayTube Live”, 2014


The Cayman Drama Society is a not-for-profit group, and like many others, is challenged in funding their activities.

“Primarily the running costs of the Prospect Playhouse are funded by show income and bar sales,” says Ebanks. “However, for maintenance and refurbishments of the playhouse, and improving our technical abilities with regard to sound and lighting, we rely on funds raised from our patrons – both corporate and individual.”

A small amount is also raised from membership dues.

“Side by Side by Sondheim”, 1999

“We are currently embarking on an expansion to the theater, so we are seeking sponsors and patrons to this purpose,” says Ebanks. “This will include naming rights to a small ‘black box’ theater, our training space, a stage door entrance, lobby, box office, and a new balcony.”

Upcoming performances

The Playhouse’s upcoming performances are: “Page to Stage: A Showcase of the Adult Summer Intensive Class” on Aug. 25; “Sistahs” from Sept. 7–23 on Thursday, Friday, Saturday at 7:30 p.m.; “Cambridge American Shakespeare: A Midsummers Night’s Dream” on Sept. 26–28; and “A Playhouse Family Christmas” on Nov. 24–Dec. 2 at 7:30 p.m. on Thursday, Friday and Saturday, and Nov. 26 and Dec. 4 matinees at 4 p.m.

To find out more about the history of the Cayman Drama Society, upcoming shows and volunteering, you can speak to current society members or visit the society’s website at Those interested in the training program should email [email protected]

“Wit”, 2010
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