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Madye Lee Chastain was born on December 15, 1908, in Texarkana, Texas. While her childhood was primarily spent in the city, Chastain's summer vacations on her grandmother's farm profoundly impacted her; the memories of those summers stayed with her through adulthood and became the inspiration for her one of her children's books. Chastain would later say that her life experiences would infuse all of her creative work in some way.

After high school, Chastain's family moved to Atlanta, Georgia, where she attended Oglethorpe University and the Art School of High Museum. After moving to New York City with her parents, Chastain continued her art studies at Grand Central Art School and Columbia University.

Art would play a major role in Chastain's life. She married another artist, Henry Kurt Stoessel and worked as an artist for a period of six years. When her daughter Roxanna was born in 1939, Chastain became interested in the wealth of children's books available, an interest that expanded into creating her own children's stories for her daughter. The first book that she wrote was about Roxanna, an endeavor that launched Chastain into her career in children's book writing and illustrating. Over the space of six years, Chastain wrote and illustrated ten books for children.