Set in Prohibition era Chicago, bootlegger Robbo and his cronies refuse 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, believing he has avenged her father's death, the gangster donates to an orphanage, cementing his reputation as a softhearted hood.
Frank Sinatra
as Robbo
Dean Martin
as Little John
Sammy Davis Jr.
as Will Scarlet
Bing Crosby
as Allen A. Dale
Peter Falk
as Guy Gisborne
Barbara Rush
as Marian Stevens
Victor Buono
as Deputy Sheriff Alvin Potts
Edward G. Robinson
as Big Jim Stevens (uncredited)
Hank Henry
as "Six Seconds"
Robert Foulk
as Sheriff Octavius Glick
Allen Jenkins
as Vermin Witowski
Jack La Rue
as Tomatoes
