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
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
Jimmy 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)
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