[1][2] Most recognized as an independent writer and director, Greenwald’s most notable films include Sophie and the Rising Sun (2016), starring an ensemble cast that included Margo Martindale, Julianne Nicholson, Lorraine Toussaint and Diane Ladd, Songcatcher (2000) starring Aidan Quinn and Janet McTeer and introducing Emmy Rossum, and The Ballad of Little Jo (1993), starring Suzy Amis and Ian McKellen.

She also directed an adaptation of Jim Thompson's The Kill-Off featuring an ensemble cast that included Cathy Haase and the film debut of Jorja Fox.

Greenwald went on to write and direct her groundbreaking Western, The Ballad of Little Jo (1993), which was released worldwide by Fine Line Features and Polygram Filmed Entertainment.

[4][5][6] The film is also one of the primary subjects of Modleski’s Old Wives Tales and Other Women’s Stories, which explores “the phenomenon of female authors and performers who ‘cross-dress’ - women, that is, who are moving into male genres and staking out territory declared off-limits by men and by many feminists.”[7] Subsequently, Greenwald wrote and directed Songcatcher (2000).

Her numerous TV movies include What Makes a Family, starring Brooke Shields, Whoopi Goldberg, and Cherry Jones.

She also directed the non-air pilot for a show that evolved into Backyardigans and an episode of Wildfire for ABC Family (now Freeform).