This article amplifies the intersection of musical theatre and political discourse during Donald Trump’s presidency by working against Trump’s imperative that musical theatre be a ‘safe’ art form. Rather than evaluating how Trump identifies with and mobilizes musical theatre numbers from Broadway’s megamusicals era, I assess how performers and multimedia artists critique Trump through musical theatre citation. In doing so, I argue that musicals, as a pervasive and emotionally resonant art form, serve as an effective vehicle for satire and political commentary in the digital era. This study tracks how Broadway artists like Patti LuPone leveraged community star power to challenge Trump’s rhetoric and actions, while performers like Randy Rainbow created online spoofs of well-known musical numbers to chronicle contemporary politics and inspire direct voting action. Finally, it moves to paratheatrical art in the work of graffiti artist TABBY, who used iconic musical imagery in pieces like The Lying King to appraise Trump’s political character. By recontextualizing musical numbers within political events and exploring their use in both supportive and critical contexts, I underscore the enduring influence and democratic potential of musical theatre in shaping and reflecting cultural and political narratives.