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.

Don Siegel’s classic crime thriller "Charley Varrick," made in 1972 in the wake of the immensely successful "Dirty Harry," stars Walter Matthau in what is probably the actor’s finest dramatic role, airshow pilot turned crop duster turned bank robber turned mob target Charley Varrick. This feature-length documentary takes the viewer back to the time of the shooting of this cult item and features original interviews with Siegel’s son, Kristoffer Tabori, actors Andy Robinson and Jacqueline Scott, stunt driver and actor Craig R. Baxley, composer Lalo Schifrin and Howard A. Rodman, whose father co-wrote the screenplay.

With a focus on Clint Eastwood's career as a director, this documentary features movie clips, behind-the-scenes footage, interviews with people with whom he has worked, as well as comments from Clint Eastwood himself.

Short featurette showcasing Clint Eastwood, film historian and critic Richard Schickel and producer Robert Daley, who speak about Eastwood’s work as an actor, as well as other characters he portrayed at that time.

Ed Okin used to have a boring life. He used to have trouble getting to sleep. Then one night, he met Diana. Now, Ed's having trouble staying alive.

Harold, a professional gambler, and his girlfriend Bonita, a lounge singer, follow Willie, a young blackjack dealer, around the western U.S. Harold has a jinx on Willie and can't lose with him. Bonita and Willie meet and fall for each other and plot to do away with Harold and collect on his life insurance.

Documentary about director Don Siegel including interviews with Siegel and clips from his movies.

The residents of San Francisco are becoming drone-like shadows of their former selves, and as the phenomenon spreads, two Department of Health workers uncover the horrifying truth.

Charley Varrick robs a bank in a small town with his friends, but instead of obtaining a small amount of money, they discover they stole a very large amount of money belonging to the mob. Charley must now come up with a plan to not only evade the police but the mob as well.

When a madman dubbed 'Scorpio' terrorizes San Francisco, hard-nosed cop, Harry Callahan – famous for his take-no-prisoners approach to law enforcement – is tasked with hunting down the psychopath. Harry eventually collars Scorpio in the process of rescuing a kidnap victim, only to see him walk on technicalities. Now, the maverick detective is determined to nail the maniac himself.

A promotional short on the movie Dirty Harry (1971) , which compares it to such classics as 'G' Men (1935) or The Big Sleep (1946), focusing on the toughness of those movies' main characters.

A brief fling between a male disc jockey and an obsessed female fan takes a frightening, and perhaps even deadly turn when another woman enters the picture.

The Beguiled: The Storyteller is the first documentary short ever directed by Clint Eastwood. Shot in Baton Rouge, Louisiana, under the Malpaso Production Company, it has a running time of 12 minutes and provides a behind-the-scenes look at the making of the 1971 film, The Beguiled. Eastwood highlights each of the primary actors including himself as well as director Don Siegel.

Deputy Marshal Sam McCloud of the small western town of Taos, New Mexico is assigned to the metropolitan New York City Police Department (NYPD) as a special investigator.

Middle-aged suburban husband Richard abruptly tells his wife, Maria, that he wants a divorce. As Richard takes up with a younger woman, Maria enjoys a night on the town with her friends and meets a younger man. As the couple and those around them confront a seemingly futile search for what they've lost -- love, excitement, passion -- this classic American independent film explores themes of aging and alienation.

Coogan, an Arizona deputy sheriff goes to New York to pick up a prisoner. While escorting the prisoner to the airport, he escapes and Coogan heads into the city to recapture him.