Toby Grisoni (Adam Driver), an advertising director, is struggling with the production of a commercial featuring Don Quixote and Sancho Panza in rural Spain. Whilst in a restaurant after an unsuccessful day of shooting, Toby's superior, the Boss (Stellan Skarsgård), recommends he find inspiration and brings over a Gypsy (Óscar Jaenada) who sells him an old DVD of ''The Man Who Killed Don Quixote'', an amateur black-and-white film that Toby coincidentally wrote and directed ten years before as a student. Nostalgic, Toby watches the film, so enthralled that he barely notices the seductions of the Boss's wife Jacqui (Olga Kurylenko) in her hotel room. When the Boss returns, Toby frantically escapes, taking the DVD whilst managing to disguise himself by wearing a Gypsy's hat that Jacqui took.