The play premiered off-Broadway at Playwrights Horizons on November 18, 1988 and closed on February 19, 1989 after 99 performances. It then transferred to Broadway at the Plymouth Theatre, opening on March 9, 1989 and closing on September 1, 1990, after 622 performances. Both productions were directed by Sullivan, with a cast that starred Joan Allen as Heidi, Boyd Gaines as Peter, and Peter Friedman as Scoop. Sarah Jessica Parker was featured in three small roles off-Broadway; those roles were played by Cynthia Nixon for the Broadway run.
The first major production mounted after Wasserstein's death in January 2006 was at the Berkshire Theatre Festival during the summer of 2006.
The plot follows Heidi Holland from high school in the 1960s to her career as a successful art historian more than twenty years later. The play's main themes deal with the changing role of women during this time period, describing both Heidi's ardent feminism during the 1970s and her eventual sense of betrayal during the 1980s. Though most of the characters are women, there are two important male characters; Peter Patrone, a gay pediatrician who is arguably Heidi's best friend, and Scoop Rosenbaum, a magazine editor who marries and has many affairs, and with whom Heidi has a tense friendship.
The New York Times critic Mel Gussow wrote of the Playwrights Horizon production: "Ms. Wasserstein has always been a clever writer of comedy. This time she has been exceedingly watchful about not settling for easy laughter, and the result is a more penetrating play. This is not to suggest, however, that The Heidi Chronicles is ever lacking in humor."