Music Comedy Crime
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.
Directed by
Gordon Douglas
Written by
David R. Schwartz
Peter Falk
Guy Gisborne
Larri Thomas
Dancer
Michael Jeffers
Nightclub Patron
Al Bain
Hood
Victor Buono
Deputy Sheriff Alvin Potts
Dean Martin
Little John
Frank Sinatra
Robbo
Richard Bakalyan
Robbo's Hood
Bing Crosby
Allen A. Dale
Barbara Rush
Marian Stevens
Edward G. Robinson
Big Jim Stevens
Paul Frees
Radio Announcer (voice) (uncredited)
Sig Ruman
Hammacher (uncredited)
Toni Basil
Flapper (uncredited)
Tony Randall
Hood (uncredited)
Billy Curtis
Newsboy
Bill Zuckert
Jury Foreman
Manuel Padilla Jr.
Orphan Boy
Jerry Davis
Orphan Boy (uncredited)
Hans Conried
Mr. Ricks (uncredited)
Jeffrey Sayre
Courtroom Spectator (uncredited)
Chuck Hicks
Factory Worker
Arthur Tovey
Juror (uncredited)
Joseph Ruskin
Twitch
Bernard Sell
Club Patron
Larry D. Mann
Workman
Diane Sayer
Booze's Witness
Bert Stevens
Nightclub Patron / Sidewalk Passerby (uncredited)
James Dime
Hood
Sammy Davis Jr.
Will Scarlet
Charles Sherlock
Pool Game Spectator
Francis McDonald
Old Man at Robbo's Club
Mickey Finn
Bartender
Phil Arnold
Hatrack
Allen Jenkins
Vermin Witowski
Jack La Rue
Tomatoes
Barry Kelley
Police Chief Oscar C. Brockton
Dick Simmons
Prosecutor
Al Wyatt Sr.
Hood
Robert Carricart
Blue Jaw
Maurice Manson
Dignitary
Robert Foulk
Sheriff Octavius Glick
Harry Wilson
Gisborne's Hood
Herschel Graham
Juror (uncredited)
Kenner G. Kemp
Nightclub Patron (uncredited)
Eugene Jackson
Congregation Member
Frank J. Scannell
Robbo's Lawyer
Richard Sinatra
Gisborne's Hood
Sayre Dearing
Courtroom Reporter / Nightclub Patron (uncredited)
Dick Johnstone
Club Patron
Al Silvani
Robbo's Hood
Eve Bernhardt
Woman
Linda Brent
Derelict
Boyd 'Red' Morgan
Jakes
Jimmy Van Heusen
Hank Henry
"Six Seconds"
Harry Swoger
Soupmeat
Bernard Fein
Charlie Bananas
Sonny King
Robbo's Hood
Phillip Crosby
Robbo's Hood
Caryl Lee Hill
Cocktail Waitress
Jim Michael
Hood (uncredited)
George Boyce
Derelict (uncredited)
Chet Allen
Hood
Monya Andre
Spectator at Dedication
Walter Bacon
Derelict
Benjie Bancroft
Bailiff
Oscar Blank
Derelict
Joe Brooks
Gisborne's Hood
Robert Buckingham
Croupier
James J. Casino
Hood
Michael Cirillo
Derelict
Robert Cole
Congregation Member
Thom Conroy
Dawson
Anne D'Aubray
Woman
Ronnie Dayton
Bit Part
John Delgado
Hood
Joe Evans
Congregation Member
Ben Frommer
Derelict
Joe Garcio
Derelict
Rudy Germane
Club Patron
Joseph Glick
Hood
George Golden
Police Officer
Jack Gordon
Bartender
Ken Grant
Dancing Orphan
Joe Gray
Hood
Buck Harrington
Passerby
Ed Haskett
Juror
Chester Hayes
Organ Grinder
Lars Hensen
Club Patron
Chris Hughes
Jud
Joey Jackson
Butler
Johnny Kern
Worker
Joseph La Cava
Juror
Mike Lally
Attorney
Clarence M. Landry
Congregation Member
Primo López
Worker
Jo Ann March
Woman
John Marlin
Hood
Alan Marston
Courtroom Spectator
Mathew McCue
Derelict
Carolyn Morin
House Girl
George Nardelli
Spectator at Dedication
Eddie Ness
Robbo's Lawyer
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
Mark Sherwood
Orphan Boy
Mabel Smaney
Derelict
Martin Strader
Passerby
Blaine Turner
Police Officer
Shirley Wilson
Courtroom Spectator
Marc Winters
Orphan Boy
John Zimeas
Hood
Jack Baker

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