Robin and the 7 Hoods (1964): Douglas’ Musical Film, Starring the Rat Pack (Sinatra, Martin, Davis, but not Lawford)

The main reason to see Gordon Douglas’ musical film is its cast, which, in addition to the Rat Pack—Frank Sinatra, Dean Martin, Sammy Davis Jr.—also includes Bing Crosby and Peter Falk.

Edward G. Robinson makes an uncredited performance.

As penned by David R. Schwartz, the tale shifts the Robin Hood mythology to 1930s Chicago and gangster setting.  The only major deviation is the character of Maid Marian, who is anything but faithful, played by Barbara Rush.

Produced by Sinatra, then at the peak of his singing and acting career, the film introduced the hit song “My Kind of Town,” by Jimmy Van Heusen and Sammy Cahn, which was nominated for the Best Original Song Oscar, and became part of Sinatra’s repertoire.

Robinson plays “Big” Jim Stevens, boss of Chicago’s underworld, as he gets an unexpected birthday present from his ambitious lieutenant, Guy Gisborne (Falk), he gets shot by the guests.

Taking over, Gisborne orders the town’s other gangsters to protection money, vowing it’s still “All for One.”  Fellow gangster Robbo (Sinatra) is resentful and a gang war erupts.

Robbo recruits pool hustler Little John (Martin), who sings “A Man Who Loves His Mother,” and quick-draw artist Will (Davis Jr.) and some others but they are still outnumbered, not to mention that corrupt Sheriff Octavius Glick is on Gisborne’s payroll. Gisborne and Robbo decide to destroy the other’s gambling joint on the same night, and Will sings “Bang! Bang!”

Big Jim’s educated daughter, Marian (Barbara Rush) asks Robbo to avenge her father’s death, which he refuses.

After the sheriff is disposed, Marian offers Robbo $50,000, assuming he did the job. When Robbo refuses, Marian hopes he’ll  take over the town. She then sends the money to his gambling club, and Robbo donates it to an orphanage.

Alan A. Dale (Crosby), the orphanage’s director, is impressed with the philanthropic gesture, a Chicago gangster who robs from the rich and gives to the poor.

Delighted at the free publicity, Robbo invites Dale to handle the gang’s charities, the Robbo Foundation, opening soup kitchens, free clinics and orphan shelters, exploiting the Robin Hood image, under tutelage from Robbo and Little John (“Style”).

Gisborne and new sheriff Potts organize a police raid, but Robbo outsmarts then and disguises the club as a mission. The sheriff and Gisborne Robbo’s gang singing gospel songs and preaching the sins of alcohol, complete with hymnals and tambourines (“Mr. Booze”).

Robbo is framed for Glick’s murder, with Gisborne and Potts claiming that Robbo had planned it. Dale teach the despondent orphans to view it as a lesson (“Don’t Be a Do-Badder”). The jury finds Robbo innocent, and he, in a green suit, thanks Chicago (“My Kind of Town”).

However, the charities have become a front for counterfeiting; there are fake bills in soup cans. Marian is willing to keep Robbo as a front, but he leaves in contempt. Later, he tells her to leave town, but she starts a Women’s League for Better Government to frame Robbo for the counterfeiting, and he and gang flee. They are reduced to working as Santa Clauses to solicit charitable donations.

Lawford was originally cast as Dale, but was replaced with Crosby after a falling out with Sinatra. The shoot proved to be troubled for Sinatra due to the assassination of President Kennedy and the kidnapping of his son, Frank Sinatra Jr., who was held for ransom.

In some moments, the film feels like a spoof of gangster movies, especially evident in Falk’s comic performance.  In others, the film strains in adapting Robin Hood fable to modern times, recalling in tone the Damon Runyon tales.

Crosby, still a major movie star who had top billing over Sinatra in their musical High Society, sang more songs than Sinatra in this picture.

“My Kind of Town” is sung, in various versions, including during the opening and closing credits.