A founding member of the National Portrait Gallery in 1911, Glyn Philpot was a British painter and sculptor, celebrated for his portraits of contemporary figures. In his painting of Penelope he depicts an episode from Homer’s Odyssey in which Penelope, the wife of Odysseus, weaves a shroud.

Continually unravelling the shroud at night, Penelope forestalls the one hundred suitors who hope to marry her whilst her husband, Odysseus, is away fighting the Trojan War. Begun during a trip to Florence, the gentle colours of the painting imbue the scene with a sense of tranquillity; however, the painting’s subject expresses a powerful sense of repressed sexuality.
The preparatory studies for the painting indicate that Philpot used a male nude to model the male figure on the left and his sister, Daisy, as the seated Penelope. The initial compositions do not include the ‘clamys’, an ancient Greek cloak, that serves to cover the man’s bare buttocks.

Many of Philpot’s paintings feature portraits of men, and in particular the male nude. With the three male suitors occupying much of the canvas space in Penelope, the composition of the painting thus typifies Philpot’s focus on the male presence in his paintings. Philpot was both a practicing Roman Catholic, and a homosexual man, and as such many of his paintings reflect his efforts to gradually accept with his sexuality.

In this artwork, Penelope is depicted in a three-quarter profile, her gaze directed slightly downward with an air of introspection. Philpot's use of light and shadow creates a sense of depth and dimension, emphasizing the contours of Penelope's face and accentuating her features. The subtle nuances of her expression convey a quiet strength and resilience, hinting at the depth of her character and inner world. Philpot's meticulous attention to detail is evident in the rendering of Penelope's attire and accessories, from the intricate folds of her clothing to the delicate strands of pearls adorning her neck.