Robin and the Seven Hoods (1964)

Synopsis
The Rat Pack packed it in after this sprightly musical comedy that owes more than it should to Damon Runyon's stories and Frank Loesser and Abe Burrows's classic musical Guys and Dolls. Sammy Cahn and Jimmy Van Heusen's bright and snappy score features such songs as "Style", "Bang-Bang" and the Sinatra standard "My Kind of Town". Set in 1920s Chicago, the tale begins during a birthday party for head mobster Big Jim (Edward G. Robinson) who is shot to death during the celebration. Rival gangster Guy Gisbourne (Peter Falk) immediately declares himself the chief gangster. The northside gang, headed by Robbo (Frank Sinatra) is willing to grant Guy his self-declared title as long as he leaves the northside territory alone. Guy refuses and when small time hood Little John (Dean Martin) joins Robbo's crew, turf warfare breaks out between the two gangs, resulting in the destruction of both Robbo and Guy's nightclubs. Meanwhile, Big Jim's daughter Marian (Barbara Rush) offers Robbo $50,000 to find the man who killed her father. Robbo demurs and gives the money to his henchman Will (Sammy Davis Jr.) to get rid of. Will, hoping to do a good deed, hands the money over to Allen A. Dale (Bing Crosby), who runs an orphanage. Allen, finding out that the money came from Robbo, informs the newspapers of Robbo's philanthropic enterprise and Robbo immediately becomes a local celebrity, referred to as Chicago's Robin Hood. For his part, Robbo is willing to go along with the publicity. On the romantic front, although Robbo is attracted to Marian, he gives her the brush-off when he finds she is using a charitable foundation as a front for a counterfeiting ring being run by herself and Little John. Robbo tells Marian to leave town. Instead, she hooks up with Guy, proposing that he kill both Robbo and Little John. ~ Paul Brenner, All Movie Guide