Published in 1949, Millay’s poem anticipates elements of Postmodernism, a literary movement that would not officially arrive until later in the 20th century. Yet Millay’s work features a few Postmodern hallmarks such as playfulness and intertextuality. Postmodern authors, like Kathy Acker, often incorporated outside texts into their work, and Millay’s work incorporates Homer’s text The Odyssey. She engages with the poem playfully by creating a speaker who identifies with Penelope and appears to speak for her. She also plays with language by spelling Odysseus as Ulysses, as if she were referring to James Joyce’s classic Modernist novel Ulysses. In Joyce’s text, the chapters take their names from episodes in The Odyssey. The final chapter is “Penelope,” told from the female character Molly Bloom’s perspective, a larger-than-life woman who has been mostly silent while the male characters take center stage. Molly identifies as Penelope, and her soliloquy, like the speaker’s in “An Ancient Gesture,” is intimate and emotional, critically one of the most revealing chapters in the narrative.

Millay’s work also points toward Modernism and its emphasis on individuality and its doubts about grand ideas and progress—a suspicion shared by Postmodernists. In “An Ancient Gesture,” the notion of work comes across as futile as the process of weaving continues infinitely and never produces a finished product. Postmodernists and Modernists also believed reality wasn’t objective but a result of an individual's perceptions. Through the lens of the speaker and Penelope, Millay’s poem creates a world in which female crying is a tradition worthy of celebration.

Finally, Millay explicitly places the poem in the context of ancient literature. To gain a deeper understanding of the poem, some information about Queen Penelope and King Ulysses (Odysseus) is useful. Ulysses went off to fight in the Trojan War and had an onerous time returning home. He faced lotus-eaters, sirens, a one-eyed monster, vengeful gods, and a nymph. Eventually, his son Telemachus tracks him down, and they return to Ithaca and take out Penelope’s scheming, lecherous suitors. Back in Ithaca, Penelope already devised a plan to waylay the suitors: She told them she had to weave a shroud for Ulysses’s dad Laertes before she could remarry. Penelope purposefully undid her work each night so she could remain faithful to her husband who, as Millay’s speaker says, “has been gone […] for years” (Line 7).