From the time when Edgar Allan Poe’s “The Pit and the Pendulum” was first illustrated by Julian Portch (London: Clarke, 1853) until now, the representation of this sensational tale has attracted the attention of readers, editors, and illustrators. Our chapter focuses on how artists have recreated the claustrophobic space that Poe painted so effectively with his own words, as not only a space intended for physical but also psychological torture. Despite having been represented recurrently by well-recognized artists in Poe graphic history—including Jules-Descartes Férat (1884), Alfred Kubin (1910), Harry Clarke (1919), Arthur Rackham (1935), Gus Bofa (1941), William Sharp (1941), and Hans Fronius (1959)—this tale remains an enduring source of inspiration for visual artists. Because this is the only tale by Poe set in Spain (Toledo), we pay special attention to Spanish illustrators like F. Xumetra Ragull (1887), Ramon Calsina (1971), and María Espejo (2017).