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