The historical comedy film Bill (2015) exploits and interprets a missing piece in Shakespeare’s biography. Written by and starring the principal performers of children’s comedy series Horrible Histories (2009–2013), it reconstructs the playwright’s ‘lost years’ within an anachronistic period setting and presents the world of Elizabethan England liberally peppered with references to contemporary pop culture. My chapter begins with an exploration of how Bill’s origins can be found in group’s early work on Horrible Histories and the dissimilarities between the fictional Shakespeares represented in the series and film. I then consider the particular category of Shakespearean bio-fiction under which Bill can be filed, its connections to the period TNT drama series Will (2017), and explore how it can be contextualised as both a prequel to Shakespeare’s success and an exploration of his lost years. This is followed with analysis of Bill’s incongruous references to modern popular culture, intertextual use of quotations and its position as an ‘origin story,’ in a tradition which evokes and capitalises on the popularity of superhero films in the twenty-first century. Finally, I investigate the film’s central relationship between Shakespeare and Marlowe and how the writers simultaneously satirise and celebrate the notion of artistic collaboration between the two playwrights. Throughout this chapter, Bill’s importance to the critical conversation about how and why makers of film and television are continually drawn to Shakespeare’s life is underlined through comparison with other onscreen representations of the playwright that blend historical fact and biographical fiction.