Arrival of an Ingenue: 'Roman Holiday' (1953) and 'Pretty Woman' (1990) with Sydney Duncan

The Sleepless Cinematic Podcast · Mar 11, 2026 · 2h 6m

This week, Julian, Emilio, and Madeline are joined by comedian Sydney Duncan to discuss two films that launched their leading ladies to superstardom - William Wyler’s “Roman Holiday” from 1953 and Garry Marshall’s “Pretty Woman” from 1990. The group draws comparisons both salient and subtle, and examines the aspects of Audrey Hepburn and Julia Roberts’ performances that solidify these roles as their breakouts. The group also discusses the role that class plays in each of these films and the relationships at their center. Among the many similarities, they also observe that one of the…