Her debut feature film, 1998's semi autobiographical Slums of Beverly Hills which she both wrote and directed, played at both Sundance and the Cannes film festival. Based on her own experience growing up in Beverly Hills in the 1970s, Slums is a dark comedy about growing up broke in glitzy Los Angeles. Using photographs Jenkins had kept from her time at Beverly Hills High School, Art Director Scott Plauch and Production Designer Dena Roth were able create an accurate period depiction of Beverly Hills, while also staying true to the autobiographical element key the film's success. Starring Alan Arkin, Natasha Lyonne and Marisa Tomei, the film was nominated for two Independent Spirit Awards (Best First Feature and Best First Screenplay) and has since become a cult hit. Jenkins took a nearly decade-long hiatus to complete her next feature film. In the nine-year gap between her two films, she worked on an eventually abandoned screenplay about Photographer Diane Arbus. Before returning to her next feature film, Jenkins branched out to explore theater, essay publications, and non-profit film and TV work. In 2003, Tamara directed The New Group's theater production of A Likely Story, written and performed by David Cale.