Caldicott has a strong history of Drama through the presentation of Junior Middle and Senior School productions. However, in 2005 drama was introduced to parts of the school in the academic timetable, and since 2006 has been included into the teaching curriculum for all boys in the Junior and Middle schools.

Drama teaching is delivered by professional drama teachers every week, and boys in the First, Second and Third Forms receive a 30 minute period, while boys in the Fourth Form receive a 60 minute session. During these classes boys develop confidence and build up their technical knowledge and practical skills in areas such as mime, improvisation, and script work. In the Fourth Form this includes working towards a Trinity Guildhall speech and drama exam which every boy will take during that year. The work preparing for these exams specifically provides a strong basis for the preparation involved in any subsequent Scholarship applications or auditions.

The training and study in general will build students’ confidence, sensitivity and awareness of physicality, social skills, team-building and co-operation skills, as well as specific experience in public speaking, self discipline and critical appreciation which can then be applied in other areas of performance, such as a school production or the Declamation and Public speaking Competition in which every boy takes part. Importance is placed upon learning through practical performance, trial and error, demonstration and discussion.