Robbo a.k.a. Robin (Frank Sinatra) is a 1920's era Chicago mob rival of Guy Gisborne (Peter Falk). They operate speakeasy casinos which serve booze via broads along with the little vice machines: slots, roulette, etc. Sinatra's mentor Big Jim (Edward G. Robinson, uncredited; we see his portrait in Robbo's office) has just been snatched from Chicago to go that big speakeasy in the sky thanks to a new sheriff in town. The film begins with a rather "entertaining" outdoor funeral/send off where Big Jim's fellas give him a last goodbye with some singing, throwing hats, and some pistol shots, Just like they used to do when Capone was pulling Chicago's underworld strings.
Now that Big Jim is gone, Guy Gisborne wants his operation to join with Robbo's so they can clean up the town, i.e. monopolize the gambling and the booze. Guy even says it would be better to be "the best of friends rather than the worst enemies." Robbo replies "finish your drink", meaning he's declined the offer. A new pool hustler, Little John, has come into town and wants to help Robbo with his operation. Sammy Davis Jr, has a role as one of Robbo's lackeys but, like Martin, contributes little to the actual story.
Turns out Guy is a sore loser and ransacks Robbo's speakeasy. Robbo then returns the favor. Okay, it's about a rivalry between two mob bosses. But then it gets cheesy. Interspersed with this mostly harmless but absolutely fantasized scenario of the 1920's gang wars are a lot of songs, mostly forgettable. "All for One and One for All" is sung by Falk and company at the funeral of Big Jim. "Any Man Who Loves His Mother" is sung by Dean Martin. Of course Davis has a song and dance routine where he shoots up booze bottles in "Bang Bang", and when Crosby enters the story, it's not long before he sings as well. A song which should be fast-forwarded is "Don't be a Do-Badder" in which he and the orphan boys don green Robin Hood hats and sing and dance.
Then Frankie, I mean Robbo, meets a beautiful blonde, Marian Stevens (Barbara Rush) who wants to see Robbo in private. Turns out she doesn't want a night out with Frankie. She's the daughter of Big Jim, willing to pay good money to hit whoever offed her father. The hit is carried out, but Robbo claims he had no part of it but ends with $50 G's (that's $50,000). He wants to return the money, which ends up in a charitable organization helping disadvantaged orphans run by none other than Bing Crosby as Minister Alan A. Dale. Robbo becomes an instant celebrity and labeled as the "Robin Hood" of Chicago for his charitable contributions.
It starts to ring of "Guys and Dolls" meets "Going My Way" and/or "The Bells of St. Mary's" (where Crosby played a catholic priest, Father O'Malley). "My Kind of Town", Sinatra's big solo, was nominated for "Best Song" but there's not a lot here to cheer about. The scenario didn't take itself seriously about midway.
The real standout is Peter Falk as Guy Gisborne but his role as the rival mob boss seems to have been cut in favor of endless and seemingly pointless song and dance routines. At one point Sinatra, Martin and Crosby do a song and dance routine, replete with hats and canes, as if they've been rehearsing for the latest Vaudeville show.
Not a bad premise wasted on an unbalanced if not occasionally annoying script. The musical idea essentially ruined the seriousness of the story. It still could have been a comedy-drama fantasy but adding the musical numbers clouded and crowded what could have been a decent story,
Now that Big Jim is gone, Guy Gisborne wants his operation to join with Robbo's so they can clean up the town, i.e. monopolize the gambling and the booze. Guy even says it would be better to be "the best of friends rather than the worst enemies." Robbo replies "finish your drink", meaning he's declined the offer. A new pool hustler, Little John, has come into town and wants to help Robbo with his operation. Sammy Davis Jr, has a role as one of Robbo's lackeys but, like Martin, contributes little to the actual story.
Turns out Guy is a sore loser and ransacks Robbo's speakeasy. Robbo then returns the favor. Okay, it's about a rivalry between two mob bosses. But then it gets cheesy. Interspersed with this mostly harmless but absolutely fantasized scenario of the 1920's gang wars are a lot of songs, mostly forgettable. "All for One and One for All" is sung by Falk and company at the funeral of Big Jim. "Any Man Who Loves His Mother" is sung by Dean Martin. Of course Davis has a song and dance routine where he shoots up booze bottles in "Bang Bang", and when Crosby enters the story, it's not long before he sings as well. A song which should be fast-forwarded is "Don't be a Do-Badder" in which he and the orphan boys don green Robin Hood hats and sing and dance.
Then Frankie, I mean Robbo, meets a beautiful blonde, Marian Stevens (Barbara Rush) who wants to see Robbo in private. Turns out she doesn't want a night out with Frankie. She's the daughter of Big Jim, willing to pay good money to hit whoever offed her father. The hit is carried out, but Robbo claims he had no part of it but ends with $50 G's (that's $50,000). He wants to return the money, which ends up in a charitable organization helping disadvantaged orphans run by none other than Bing Crosby as Minister Alan A. Dale. Robbo becomes an instant celebrity and labeled as the "Robin Hood" of Chicago for his charitable contributions.
It starts to ring of "Guys and Dolls" meets "Going My Way" and/or "The Bells of St. Mary's" (where Crosby played a catholic priest, Father O'Malley). "My Kind of Town", Sinatra's big solo, was nominated for "Best Song" but there's not a lot here to cheer about. The scenario didn't take itself seriously about midway.
The real standout is Peter Falk as Guy Gisborne but his role as the rival mob boss seems to have been cut in favor of endless and seemingly pointless song and dance routines. At one point Sinatra, Martin and Crosby do a song and dance routine, replete with hats and canes, as if they've been rehearsing for the latest Vaudeville show.
Not a bad premise wasted on an unbalanced if not occasionally annoying script. The musical idea essentially ruined the seriousness of the story. It still could have been a comedy-drama fantasy but adding the musical numbers clouded and crowded what could have been a decent story,