Chicago’s #1 mob boss, Big Jim (Edward G Robinson), is ceremoniously whacked at his own birthday party in Chicago during the Roaring 20s and south-side racketeer Guy Gisborne (Peter Falk) promptly takes over.
But he has reckoned without Robbo (Frank Sinatra), a protégé of Big Jim who was out of town at the time of the killing and is contemptuous of Gisborne’s ambitions, warning him to stay out of the north side. From now on, Chicago is a divided town.
Robbo and his aides – Will (Sammy Davis Jr), Six Seconds (Hank Henry) and a newcomer from the sticks, Little John (Dean Martin) – and Gisborne, backed by the crooked Sheriff Glick (Robert Foulk) and his equally crooked, but very astute, deputy (Victor Buono), enter into a battle for control of the Windy City.
Simultaneous raids are made on each other’s gambling clubs, totally wiping them out.
Robbo receives a surprise visit from a gorgeous, elegant and cool young woman called Marian (Barbara Rush), who announces that she is Big Jim’s daughter (educated at some very fancy schools) who wants to avenge her father’s death.
She offers Robbo $50,000 to rub out the sheriff, but although captivated by her steel-tipped charms, he refuses.
Marian invites Robbo to dinner at her luxurious apartment and again offers Robbo the money, but he refuses again.
Then she sends him the money by messenger, but Robbo orders Will to dump the money somewhere. He does – the Blessed Shelter Orphans Home.
The following day Robbo is hailed as “Chicago’s Robin Hood” by the newspapers. Intrigued by the image and not averse to the publicity it generates, he begins to act out a modern version of the legend.
Allen A. Dale (Bing Crosby), the threadbare and unworldly secretary of the orphanage, visits Robbo to thank him for the donation and is promptly hired to handle Robbos’ PR.
Dean Martin and Sammy Davis Jr. get most of the laughs (when they aren’t singing or dancing), Barbara Rush is very pretty and Sinatra is, well, he’s Sinatra.
Watch out for future pop star Toni Basil in a small part as a flapper.
Sammy Davis Jr.
Allen A. Dale
Jack La Rue
Edward G Robinson