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| Frank Sinatra | Robbo |
| Dean Martin | Little John |
| Sammy Davis Jr. | Will |
| Bing Crosby | Allen A. Dale |
| Peter Falk | Guy Gisborne |
| Barbara Rush | Marian Stevens |
| Edward G. Robinson | Big Jim Stevens |
| Victor Buono | Deputy Sheriff Alvin Potts |
| Barry Kelley | Police Chief Oscar C. Brockton |
| Hank Henry | Six Seconds |
| Robert Carricart | Blue Jaw |
| Allen Jenkins | Vermin Whitouski |
| Jack LaRue | Tomatoes |
| Hans Conried | Mr. Ricks |
| Sig Ruman | Hammacher |
| Robert Foulk | Sheriff Octavius Glick |
| Phil Arnold | Hat Rack |
| Harry Swoger | Soupmeat |
| Joseph Ruskin | Twitch |
| Bernard Fein | Charlie Bananas |
| Caryl Lee Hill | Cocktail waitress |
| Diane Sayer | Booze's Witness |
| Bill Zuckert | Jury Foreman |
| Milton Rudin | Judge |
| Maurice Manson | Dignitary |
Set in Chicago during Prohibition, the Rat Pack's take on the Robin Hood legend finds bootlegger Robbo and his cronies refusing to pay the greedy Guy Gisborne a cut of their profits after Guy shoots mob boss Big Jim and takes over. When Big Jim's daughter, Marian, 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.
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