The notion that Wendy Wassertstein's Pulitzer-winning play The Heidi Chronicles represented the failure of the first wave of feminism from the nineteenth and early twentieth century, and the crumbling of the second-wave of feminism, is a contentious topic that deserves continual scholarly discourse. The time-line of the play, 1965-1989, and its episodic structure, affords an accurate replication of the numerous transitions women endured, and the political seesaw they suffered in the quest for equality. The play explored the role of feminism in the lives of contemporary women, and this blatant documentation created a furor of critical controversy and paved the way for a healthy discourse, of women talking to and about women and their issues.

The Heidi Chronicles is a realistic and positive dramatization of one woman's historical journey, Heidi Holland, an art historian. Its impact actively encouraged future generations of young women to pursue their own paths in American drama. Wasserstein's unique goal as a playwright was poltical using the aesthetics of comedy in her characters' dialogue to shed a bright light on the difficulties women faced historically and are still facing today. This thesis argues that her goal was not just an exploration but a deliberate and passionate statement. The Heidi Chronicles was informed by Wasserstein's own life. She wrote this play in the manner of a chess player choosing key pieces, key characters, determined to win and solve the mystery of how women can "have it all." In interview after interview Wasserstein repeats that her writing was a way to work things out, and to search for answers to her personal questions regarding women's struggles in a male-dominated society.