Tillie Olsen's Tell Me a Riddle, penned in the 1950s before the women's movement gained full momentum, consists of four interconnected stories that have cemented their status as American classics. "Tell Me a Riddle," the titular story, was awarded the O. Henry Prize for best American short story in 1961, signaling its literary significance.

Olsen, whose parents escaped czarist Russia post-1905 revolution, provides a vivid portrayal of the working-class poor from the 1930s to the 1950s. Her narratives eschew conventional plot development, focusing instead on the intricate details of character and employing stream of consciousness to reveal their unfiltered, sometimes fragmented inner thoughts.

Many critics contend that Olsen's most compelling work mirrors her own life experiences. During the 1930s, Olsen was actively involved with the Young Communist League, and her activism led to a month-long jail stint for organizing laborers at packinghouses. In Tell Me a Riddle, the characters and various incidents reflect her personal history: her engagement with 1930s labor movements, balancing motherhood with factory and slaughterhouse work, and confronting the emotional turmoil of having a daughter, like Emily, removed from her care after abandonment by her partner. The narrative also touches on themes of solitude and alcoholism, drawing parallels to individuals like Whitey, and the poignant, difficult death of her mother from cancer. Though Olsen's writing was undoubtedly influenced by her socialist roots, her ideology evolved over time towards a more humanistic perspective, avoiding overt political proselytization and instead choosing to highlight social issues through her literary craft.

More than a voice for the proletariat, Olsen was a pioneering feminist at a time when society sought to confine women to narrow, domestic roles. With the onset of her youngest child's schooling in the 1950s, Olsen found the opportunity to write full-time in an era where American culture idolized the nuclear family and rigid gender norms. When critic Irving Howe reviewed Tell Me a Riddle in 1961, he simplistically labeled Olsen as a writer limited by her "narrow" experiences as a housewife and mother. Yet in truth, Olsen's work gives voice to those marginalized by their gender, social standing, or the nature of their labor. Despite cultural shifts over the decades, her stories retain their power and relevance, resonating with clarity, sincerity, and a passionate examination of human resilience and dignity.