Greenwald achieved some measure of notoriety with her next film, the revisionist Western "The Ballad of Little Jo" (1993), reputedly the first of its genre written and directed by a woman since the silent film era. Loosely inspired by real frontierswomen who altered their identities and lived as men, she spun a bittersweet portrait of a formerly wealthy woman undone by a bad romance and an illegitimate child. To escape the shame, Greenwald's heroine (captured by Suzy Amis in a sterling performance) created a male persona and opted to live out her life in that guise, although always fearful of discovery. Once again, the director exhibited a strong visual style and facility with actors. Although not a perfect film, "The Ballad of Little Jo" found its champions and enjoyed a modest theatrical life.
Over the course of the next six years, Greenwald concentrated on teaching at Columbia University's film school with occasional directing gigs in TV, most notably on Nickelodeon's "The Adventures of Pete and Pete". After a seven-year absence from the big screen, she returned with "Songcatcher" (2000), another period drama featuring a strong central female, in this case a musicologist researching folk music in the Appalachian Mountains. The romantic drama was selected to premiere in competition at the Sundance Film Festival.