As academic geographers continue to investigate popular geographical knowledges and imaginations beyond the bounds of academic publications, less attention has been given to moments when popular geographies reverse the gaze, expressly lifting the curtain on the production of knowledge by those of us who call ourselves professional geographers. What could turning to popular culture tell professional geographers about perceptions of our discipline, its history of complicity with imperialism, and its practices of knowledge production? This paper offers some partial answers by turning to an English popular cultural metaseries that is remarkably explicit and dynamic in its depiction of geography: Michael Bond's Paddington Bear franchise, or as Bond ironically referred to it, the “Paddington Empire.” From the very first Paddington story published in 1958 to the 2014 feature film, the Paddington franchise scrutinises geography and stages the work of professional geographical institutions, from the Royal Geographical Society to the imaginary “Geographers' Guild of Great Britain.” Drawing on archival work in Bond's collected papers, interviews, contextualising scholarship, journalism, and careful readings of the Paddington texts, I argue that the Paddington Empire iteratively reprises colonial encounters, at times in troubling ways, but also offers insightful critiques of extractive forms of geographical knowledge production.