Synopsis
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.
Cast

Frank Sinatra
Robbo

Dean Martin
Little John

Sammy Davis Jr.
Will Scarlet

Bing Crosby
Allen A. Dale

Peter Falk
Guy Gisborne

Barbara Rush
Marian Stevens

Victor Buono
Deputy Sheriff Alvin Potts

Edward G. Robinson
Big Jim Stevens (uncredited)
Hank Henry
"Six Seconds"

Robert Foulk
Sheriff Octavius Glick

Allen Jenkins
Vermin Witowski

Jack La Rue
Tomatoes

Robert Carricart
Blue Jaw

Joseph Ruskin
Twitch

Phil Arnold
Hatrack
Harry Swoger
Soupmeat
Bernard Fein
Charlie Bananas

Richard Bakalyan
Robbo's Hood
Sonny King
Robbo's Hood
Phillip Crosby
Robbo's Hood

Al Silvani
Robbo's Hood

Harry Wilson
Gisborne's Hood
Caryl Lee Hill
Cocktail Waitress

Mickey Finn
Bartender
More like this

The Sting

Some Like It Hot

King Creole

A Slight Case of Murder

Ocean's Eleven

The Damned Don't Cry

Mobsters

Welcome to Collinwood

Take the Money and Run

Angels with Dirty Faces

Johnny Dangerously

The Racket

The Roaring Twenties

The Wrong Man

I Walk Alone

Bandits

The Wild One

Private Hell 36

Two-Way Stretch

5 Against the House