This article presents the possible proximity between the philosophical tradition of pragmatism and the present-day practice of free improvisation, a musical activity that enjoys its ambiguous nature of not being clearly defined, that is, however, of value to examine as a practice in its own rights. It is used in educational and compositional contexts as a tool, as well as being an established independent performance practice, albeit for a relatively small body of audience. The discussion is led through three concepts that are utilised by pragmatists, but which resonate with the concerns of free improvisers: experience, expressive object and gesture. Outlining these key ideas, the article sheds light on John Dewey’s and Giovanni Maddalena’s thoughts on aesthetics, which provide a perspective for examining these inherent issues of free improvisation. Through a philosophical examination, the article seeks to enlighten the performance processes of the musical phenomenon of free improvisation.