A former dancer and actor, Maggie Greenwald attended film school for one year before dropping out to make shorts and work in production as both a film editor and sound editor. After spending over five years raising the necessary financing, she helmed her first feature, "Home Remedy", in 1987. Praised by VARIETY (December 23, 1987) as "involving as it is funny, thanks to a fine script and excellent thesps", the indie was a blackly comic examination of a suburban married couple's struggle to fight boredom. Greenwald turned to a Jim Thompson novel, "The Kill-Off" (1989), for a foray into film noir as her sophomore effort. Exhibited at Cannes, "The Kill-Off" attracted some attention for its ensemble acting and for the director's keen control of tone and mood. The drama about a female invalid whose gossipy manner drives those around her to violence also played at the Munich and Torino Film Festivals. Despite these prestigious showcases that her two early efforts received, neither fared well in the commercial marketplace.
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.