This paper presents the concept and the realisation of an interactive multimedia installation, called BilliArT, together with an explorative user study conducted on the data gathered during a public exhibition of the installation. The study concerns functional properties of the installation (e.g. usability, design quality) and subjective qualities of the sonic and visual feedback of the installation. The installation consists in a collaborative environment based on the carambole billiards game, which allows the users to engage in a user-driven machine-based jazz-inspired music improvisation, augmented with visual feedback. The installation is designed to promote the interaction among the users and the billiard game, stimulating the motivation to engage in the game by balancing predictable and unpredictable output, and reinforcing the feeling of reward, irrespective of their level of musical training. BilliArT introduces a new framework for expressive interaction related to the concepts of motivation and reward. The exploratory study proved the ability of the installation to activate the users’ sense of aesthetic reward, leading to a more active and satisfactory engagement in the game. Future studies may exploit these results to the advantage of the world of the arts, as well as of studies in human-computer interaction, interface design, and cultural heritage preservation.