"Eastwood: The Long Shadow" is not a standard celebration of a Hollywood icon; it is a deconstruction of the American male myth. The film operates on two timelines. The first timeline tracks Clint Eastwood in the 1960s—a frustrated, tall, awkward contract player on Rawhide who is fired for having a "bad tooth" and talking too slowly. It follows his desperate gamble to go to Italy to film a cheap western with an unknown director, Sergio Leone, where he accidentally creates the "Man With No Name" persona.
The second, more dominant timeline is set in the early 1990s. Clint is an aging icon. His recent movies (The Rookie, Pink Cadillac) are critical flops. He is seen as a dinosaur, a relic of a violent, misogynistic past. He is struggling with his turbulent breakup with Sondra Locke and fighting to get his passion project greenlit—a revisionist western script he has sat on for ten years called Unforgiven. The film explores the conflict between the violent, silent hero the world wants him to be and the sensitive, jazz-loving artist he actually is. It culminates in the filming of Unforgiven, where he finally kills his own myth to be reborn as a master filmmaker.
