Checco Zalone is the most successful Italian star over the past 15 years: his story is one of increasing success that led him to dominate the box office. Whereas his reception has been widely controversial and discussed in the flow of discourse, both film criticism and intellectual debate, in terms of political orientation (Left vs. Right), little attention has been paid to the ways in which his work and persona are promoted. Like many other comedians, Zalone’s persona benefits from a transmedia presence, as a stand-up comedian, both live and within TV shows, singer, and film star. Often, the hype around him is indebted to the resonance of his appearances, notably musical, occasionally coupled with urgent social issues. Furthermore, his transmedia persona disseminates the promotion of film works across different platforms, while his private self is mostly concealed or barely accessible. The chapter focuses on the way in which Zalone’s career epitomizes and renews allegiances between media industry sectors, on how his persona articulates notions of masculinity and nationhood, and how musical performances and parody fragment this persona and expand its outreach across various media platforms.