This chapter explores the practical realities of what it is to perform Strozzi’s music in a twenty-first century context and the artistic possibilities those realities open up, the challenges they raise, and the potentialities they create. Combining personal experience, recent classical music industry research, and cross-genre artistic ideas and insights, this chapter suggests new ways in which Strozzi’s works might be made to sing, in multiple meanings of that word. Identifying barriers to performing Strozzi’s music, this chapter then turns to Strozzi’s working practices in search of tools with which to overcome or side-step those barriers. Through sharing the author’s methods for creating new performances of Strozzi’s works, inspired by Strozzi’s example, this chapter concludes with an invitation to readers to discover their own ways of singing Strozzi today.