History lessons, in particular, and human sciences, in general, tend to be more appealing to students when film analysis or filmmaking and role play are regularly integrated in the teaching process. In the wake of the recent pandemic, which imposed remote learning, multimodal teaching strategies have gathered momentum due to their potential of increasing student creativity and insight into the topics under research, and of developing the formative goals of education. Expanding history lesson competencies, values and skills into an interdisciplinary approach to the humanities field by incorporating methods from cinematography and theatre is been proven to stimulate the authenticity of education, thus teaching sustainable citizenship. The article presents two examples on the use of film analysis and dramatization of source information as part of history lessons, which were applied successfully in the case of high school students. By aiming to implement multimodal digital methods of teaching, learning, and assessment at a systemic level, the article demonstrates that experimenting with and using the language and tools of filmmaking and improvisational theatre and dramatization has helped increase student intrinsic motivation to explore their potential vocation, has decreased absenteeism, has raised achievement levels, and enhanced the students’ overall understanding of life and wellbeing.