Documentary about sixteen actors who detail their ups and downs as they struggle to forge careers in Hollywood. They've played cops, lawyers, bosses, best friends, psychopaths, politicians and everything in between. Now you'll know who they are.

After a brief flash-forward to Frank Sinatra as an old man, saying "I miss my guys," the movie's main narrative begins during high points in the solo careers of the Rat Pack: Dean Martin has become a big success despite the breakup of his partnership with Jerry Lewis; Sinatra's career is at its peak; Sammy Davis, Jr., is making a comeback after a near fatal car crash, and standup comic Joey Bishop is gaining exposure as an opening act for the other three. The Pack becomes complete when Sinatra reconciles with actor Peter Lawford, who has been ostracized since being seen out publicly with Sinatra's ex-wife, Ava Gardner.

After seven months have passed without a culprit in her daughter's murder case, Mildred Hayes makes a bold move, painting three signs leading into her town with a controversial message directed at Bill Willoughby, the town's revered chief of police. When his second-in-command Officer Jason Dixon, an immature mother's boy with a penchant for violence, gets involved, the battle between Mildred and Ebbing's law enforcement is only exacerbated.