After a high-profile firing, everything is at stake for 40-year-old Jenna: her career, her ticking biological clock, and her bank account. Her fashion career comeback hits a snag when she falls for a charming, much younger coworker — who happens to be her boss’s son. As sparks fly, Jenna must decide if she’ll risk it all on a secret romance with the one person who could destroy her comeback.

The portrait of the last cowboy Hollywood legend dives into the 65 years of an extraordinary career in Hollywood, highlighted iconic films like The Good, the Bad and the Ugly, as well as Million Dollar Baby, Mystic River and Gran Torino all the way to Cry Macho in 2021. It is no small task to cover more than 60 years of cinema history, especially when it is trying to surveyed with such breadth and diversity: TV star, international star, controversial icon, contested director, filmmaker with a capital F, Eastwood has been through it all, experienced it all, and it is first of all this romantic trajectory, this true American pastoral that the documentary wants to tell with all the passion it possibly can.