
About
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.
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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

Dick Simmons
Prosecutor

Toni Basil
Flapper (uncredited)

Hans Conried
Mr. Ricks (uncredited)

Tony Randall
Hood (uncredited)

Sig Ruman
Hammacher (uncredited)
Jim Michael
Hood (uncredited)

Jerry Davis
Orphan Boy (uncredited)

Sayre Dearing
Courtroom Reporter / Nightclub Patron (uncredited)

Paul Frees
Radio Announcer (voice) (uncredited)
Herschel Graham
Juror (uncredited)

Kenner G. Kemp
Nightclub Patron (uncredited)

Jeffrey Sayre
Courtroom Spectator (uncredited)

Bert Stevens
Nightclub Patron / Sidewalk Passerby (uncredited)

Arthur Tovey
Juror (uncredited)
George Boyce
Derelict (uncredited)
Chet Allen
Hood

Barry Kelley
Police Chief Oscar C. Brockton

Maurice Manson
Dignitary

Bill Zuckert
Jury Foreman (uncredited)
Monya Andre
Spectator at Dedication
Walter Bacon
Derelict (uncredited)

Al Bain
Hood
Benjie Bancroft
Bailiff
Eve Bernhardt
Woman
Oscar Blank
Derelict

Linda Brent
Derelict
Joe Brooks
Gisborne's Hood
Robert Buckingham
Croupier
James J. Casino
Hood
Michael Cirillo
Derelict
Robert Cole
Congregation Member
Thom Conroy
Dawson
Roger Creed
Gisborne's Hood

Billy Curtis
Newsboy
Anne D'Aubray
Woman
Ronnie Dayton
Bit Part
John Delgado
Hood

James Dime
Hood
Joe Evans
Congregation Member
Ben Frommer
Derelict
Rudy Germane
Club Patron
Joseph Glick
Hood
George Golden
Police Officer
Jack Gordon
Bartender
Ken Grant
Dancing Orphan
Joe Gray
Hood (uncredited)
Buck Harrington
Passerby
Ed Haskett
Juror
Chester Hayes
Organ Grinder
Lars Hensen
Club Patron

Chuck Hicks
Factory Worker (uncredited)
Chris Hughes
Jud

Eugene Jackson
Congregation Member
Joey Jackson
Butler

Michael Jeffers
Nightclub Patron

Dick Johnstone
Club Patron
Johnny Kern
Worker
Joseph La Cava
Juror

Mike Lally
Attorney (uncredited)
Clarence M. Landry
Congregation Member
Primo López
Worker

Larry D. Mann
Workman (uncredited)
Jo Ann March
Woman
John Marlin
Hood
Mathew McCue
Derelict

Francis McDonald
Old Man at Robbo's Club
Jim Michael
Hood

Boyd 'Red' Morgan
Jakes
Carolyn Morin
House Girl
Richard Mosier
Singing Orphan

George Nardelli
Spectator at Dedication
Eddie Ness
Robbo's Lawyer

Manuel Padilla Jr.
Orphan Boy
John Pedrini
Hood
Leslie Perkins
Woman
Ray Pourchot
Club Patron
Paul Power
Club Patron
Paul Ravel
Worker
Clark Ross
Nightclub Patron
Myrna Ross
Flapper
Milton Rudin
Judge

Diane Sayer
Booze's Witness (uncredited)

Frank J. Scannell
Robbo's Lawyer (uncredited)
Bernard Sell
Club Patron

Charles Sherlock
Pool Game Spectator (uncredited)
Mark Sherwood
Orphan Boy

Richard Sinatra
Gisborne's Hood
Mabel Smaney
Derelict
Martin Strader
Passerby

Larri Thomas
Dancer
Blaine Turner
Police Officer
Shirley Wilson
Courtroom Spectator
Marc Winters
Orphan Boy

Al Wyatt Sr.
Hood
John Zimeas
Hood
Joe Garcio
Derelict (uncredited)
Director

Gordon Douglas
Director
Michael Daves
Second Assistant Director
Doris DeHerdt
Script Supervisor
Dolores Rubin
Script Supervisor
David Salven
Assistant Director
Lee White
Assistant Director
Creator
David R. Schwartz
Writer