Charles Macklin, the celebrated eighteenth-century actor and playwright, is now remembered as a comedian and a comedic writer; however, his first produced work as an author was the historical drama Henry VII, or the Popish Imposter. This was immediately condemned as a flop and, although it was published, it was never again produced. In this article Michael M. Wagoner examines the nature of the play’s failure by questioning the accepted narratives of theatrical success. Specifically, he engages issues of audience reception as well as the playwright’s persona to understand the combined relationship between the two dynamics that can result in a play’s failure. Ultimately, both Macklin’s persona and his later work secured the flop narrative in order to temper the subsequent expectations of his audiences. Michael M. Wagoner is a doctoral candidate at Florida State University, and he holds an MFA in Shakespeare and Performance from Mary Baldwin College. His research examines the performance and dramaturgy of early modern drama, and his essay ‘Imaginative Bodies and Bodies Imagined: Extreme Casting in Shakespeare’s The Tempest and Fletcher and Massinger’s The Sea Voyage’ will appear in The Bear Stage: Shaping Shakespeare for Performance (Farleigh Dickinson University Press, 2015).