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James Ensor’s omnivorous interest in the art of the past to rework modern art, as acknowledged, is a pivotal inspiration for his distinctive, uncanny vision of cultural modernity. His deep cross-temporal attraction to late medieval, Gothic art, especially from c. 1900s however, is less well treated, and is the core concern of this article. Discussion opens new insights into the allure of pre-modern art for Ensor’s creative practice, in the context of his exposure to the 1902 Bruges ‘Primitifs Flamands’ exhibition and its array of Flemish so-called ‘primitive’ and early German art, as well as in relation to Ensor’s interactions with a circle of artists and more globalizing interests beyond Belgium. Taking as its focus, Ensor’s evolving response to the late 19th-century urban-scape, the paper explores his potent re-workings of the medieval Dance of Death, cathedral, Christ as the Man of Sorrows and Marian iconographies, to transform the modern city and artistic experience of it into a site of liminality, alterity and difference. Turning first to Ensor’s oneiric vision of grotesques and rituals, overarched by a fantastical Gothic cathedral in his 1886 The Cathedral, discussion goes on to consider Ensor’s substantial development of these ideas in key later works: notably his 1898 Entry of Christ into Brussels and the darkly devotional, 1913 Furnes - Procession of Penitents. The paper’s final part sheds light on the close resonances between Ensor’s use of the Gothic and his contemporaries’, in particular, Edvard Munch’s and Max Klinger’s, to re-imagine the city as a space of veiled and uncanny pasts, the portals to a many-layered and different modernity.