Gellar, Peter Coyote, Stockard Channing, Joyce Van Patten, and Candice Azzara in the first production of Jake's Women Gellar has appeared in two theatrical productions. In 1986 she was Molly in the Horton Foote play, The Widow Claire. She played another Molly (Mollie at age 13) in 1990 in the Neil Simon play, "Jake's Women", but the show closed out of town after a trial run in San Diego. When Simon decided to do the play again in 1992, Gellar was the wrong age for the part and Brenda Vaccaro took the role.

"Of course, almost nothing happens in "The Widow Claire," the latest Horton Foote play to reach a New York stage. In keeping with his writing habits of four decades, the author of "The Trip to Bountiful" and "Tender Mercies" whisks us into the fictional small Texas town of Harrison and sets his characters about their diurnal business. "The Widow Claire," a 95-minute anecdote in one act, describes only a single long summer night of 1911. Horace Robedaux (Matthew Broderick), a poor but ambitious 21-year-old about to enroll in a six-week business course in Houston, spends the eve of his departure courting the title character (Hallie Foote), a 27-year-old widow with several suitors and two rambunctious kids. Daybreak brings Horace's leave-taking and an exchange of farewells so formal one might wonder whether the couple had in fact stolen a few chaste kisses under the new moon of the night before."