The 1900 Jubilee coincided with the dawn of cinema, marking a pivotal moment for the Catholic Church. This event, occurring while the pope remained confined within Vatican City due to the unresolved Roman Question, presented the Church with the unique challenge of navigating this powerful new medium. The Holy See immediately encountered two contrasting approaches to cinematic representation. The American Mutoscope and Biograph Company, driven by commercial interests, exploited existing footage of pope Leo XIII to orchestrate a global campaign of ‘Jubilee pictures of the pope’. Conversely, the Lumière brothers collaborated with the Vatican, enabling papal photographer Francesco De Federicis to capture new footage of the pope. This collaboration led to the establishment of a ‘Cinematografo Vaticano’ in front of St. Peter’s Square and the distribution of official Vatican films. The contrasting outcomes of these two approaches—the commercial success of Biograph and the limited success of the Vatican-backed venture—foreshadowed the Church’s complex and often ambivalent relationship with cinema in the decades to come. This ambivalence was further evident during the pontificate of Pius XI. While the 1925 Jubilee prohibited filming the Pope, the 1933 Jubilee saw the establishment of a Vatican-sponsored film production organisation. However, this initiative faced significant challenges, including the proliferation of unauthorised jubilee films and the ultimately unsuccessful distribution of the official Vatican-produced film.