Students discussed portraits created by Rembrandt van Rijn and Michelangelo Merisi da Caravaggio to discover the art of chiaroscuro (the difference between light and shadow) in small groups. Students investigated portrait photography of Graham Nash and Man Ray to understand how this technique has developed throughout the centuries and is still used to show intense contrast and increased dramatic impact in the arts today. From investigation of contextual references, students were in a strong position to create their own portraits by expressing emotion and playing with light to capture a theatrical self-portrait. In their small groups, students alternated roles. One student directed the composition and lighting. Another student developed digital photographing skills while the third student modelled for their portrait. This T.Y. group were a mixed ability class who were sampling art for the Leaving Certificate. Students now had top quality primary sources which they had developed by themselves. A gridding strategy was then used to map the self-portrait photographs onto canvas which helped to provide each student with a feeling of achievement. Students continued to look at painting techniques in Rembrandt and Caravaggio portraits but also in the work of Lucian Freud to observe elements such as tone and texture to complete their self-portrait painting.