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In the struggle with COVID-19, art offered a way to face the solitude of the lockdown. The focus of this paper is primarily on Caravaggio's painting The Seven Works of Mercy, with references to other paintings to amplify some aspects of the artist's approach to life and his uniqueness in the artistic landscape of his time. Darkness was part of Caravaggio's research for spiritual truth and by entering the stories of his life and exploring the tales told through imaginative expression in his paintings, it is possible to understand his process of exploration of ancestral darkness. The author uses her imagination to reflect on how art can help to contact the profound fears buried in the unconscious which are now being awakened by the pandemic. The contemplation of this painting facilitated the emergence of emotions related to the darkness of our time, with the discovery that empathy and mercy offer a way to come to terms with the pandemic. This approach demands a different understanding of reality with Caravaggio's dark creative world becoming a companion that permits the exploration of what is not yet thinkable in daily life. Images accompany the author's research that relies on her imagination and amplifications.