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Traditional American musicals have often portrayed women in conventional, domestic roles like wives and mothers. Sondheim and Lapine’s Into the Woods (1987) abounds with maternal figures who, at first, appear musically and lyrically complex. The musical’s mothers transgress the confines of housekeeping and childrearing to pursue sexual fantasies, provide for and protect their children and explore their personal and emotional bonds. However, the actions of such transgressive mothers, including the Baker’s Wife, Jack’s Mother and the Witch, are narratively renounced, their agency contained and their stories cut short with fatal punishments. In contrast, Cinderella, the epitome of the pure good woman, prevails as the solitary mother figure of the show’s concluding family. This article argues that despite its overtures towards something more complex, Into the Woods’ depiction of motherhood merely reinforces reductive, patriarchal genre standards.