 Her father and brother died when she was sixteen in a pontoon plane accident during an Alaskan fishing trip.A National Merit Scholarship Program finalist in high school, she attended Swarthmore College in Pennsylvania for three years before taking up acting classes at New York University; she eventually graduated from The New School for Social Research.Early in her acting career, Littleford worked in improvisational theatre with the Chicago City Limits group, founded a sketch comedy troupe, and wrote her own one-woman show, "This Is Where I Get Off", which she performed with the Circle Repertory Company.