Robin and the Seven Hoods (1964)

Set in Chicago during Prohibition, the Rat Pack's take on the Robin Hood legend finds bootlegger Robbo (Frank Sinatra) and his cronies refusing to pay the greedy Guy Gisborne (Peter Falk) a cut of their profits after Guy shoots mob boss Big Jim (Edward G. Robinson) and takes over. When Big Jim's daughter, Marian (Barbara Rush), gives Robbo a large sum of money, believing he has avenged her father's death, the gangster donates it to an orphanage, cementing his reputation as a softhearted hood.