Orson Welles, a boy from Kenosha, Wisconsin, was one of the most audacious Shakespearians who ever lived. He recited soliloquies as a child, wrote a book on the plays as a teenager, and at age 17 roamed across Ireland before brazenly (and successfully) presenting himself at the Abbey Theatre as a distinguished American actor. Welles also created three of the most ambitious Shakespeare films. As an American pretender, a colonial presuming to re-interpret the greatest British writer, Welles approached Shakespeare with a mix of bravado and insecurity. This paper explores how Welles' American nature informs these roles and, especially, his final Shakespeare film, Chimes at Midnight (1965). In this production, Welles plays Falstaff and is understandably identified with the role, but it could be argued that he speaks more directly through Prince Hal, whose anxiety about inheriting the throne might be reflected in the way an American Shakespearian seeks to be accepted by the British keepers of the text. The words of Hal's father, Henry IV- Uneasy lies the head that wears the crown -might apply to Welles' American-inflected depictions of kings and princes who do not entirely believe in their own royal agency. The tension between Welles‘ brashness and his fretfulness created some of the most memorable Shakespeare in the cinema.