Beppe Caschetto is one of the most important and influential figures in the Italian film, television and media sector. With his talent agency, he has created, sustained, and shaped many successful Italian performing careers, taking a systemic approach to actors’ personal and professional development. He has helped them to transcend the boundaries between film and television and between fiction and entertainment, and to build enduring profiles on the national media and entertainment scene, often managing “packages” of talents that leverage his star names’ strengths to develop or support other professionals. With his production company, he builds media products around his portfolio of performers and enjoys an increasingly significant share of Italy’s audiovisual production pie. Through Caschetto’s rare interviews (he is not a public figure and eschews the limelight), this chapter fleshes out his profile as a key intermediary and investigates the roles and skills he has mastered in managing his acting talent in Italy’s contemporary media landscape.