This chapter focuses on the eccentric and heterogeneous experiences, interests, and influences that contributed to the development of Sergio Leone’s authorial identity, particularly in the sword-and-sandal and Spaghetti Western genres. It investigates the exceptional intersection of cultural, technical, stylistic, and ideological influences coming from different, often contradictory, directions, creating a complete portrait of the artist. The chapter provides an overview of Leone’s career, and it also emphasizes his experience in roles other than that of film director, from assistant director on De Sica’s Bicycle Thieves and many Hollywood epics, to producer of films such as My Name is Nobody (1973) by Tonino Valerii and Fun is Beautiful (1980) by Carlo Verdone. The chapter therefore reconstructs Leone’s background and puts it into communication with the historical, cultural, and cinematic national and international contexts from Fascism up to the director’s death in 1989.