Summary
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
Robert Foulk
Sheriff Octavius Glick
Allen Jenkins
Vermin Witowski
Jack La Rue
Tomatoes
Robert Carricart
Blue Jaw
Joseph Ruskin
Twitch
Phil Arnold
Hatrack
Richard Bakalyan
Robbo's Hood
Al Silvani
Robbo's Hood
Harry Wilson
Gisborne's Hood
Mickey Finn
Bartender
Dick Simmons
Prosecutor
Toni Basil
Flapper (uncredited)
Hans Conried
Mr. Ricks (uncredited)
Tony Randall
Hood (uncredited)
Sig Ruman
Hammacher (uncredited)
Jerry Davis
Orphan Boy (uncredited)
Sayre Dearing
Courtroom Reporter / Nightclub Patron (uncredited)
Paul Frees
Radio Announcer (voice) (uncredited)
Kenner G. Kemp
Nightclub Patron (uncredited)
Jeffrey Sayre
Courtroom Spectator (uncredited)
Bert Stevens
Nightclub Patron / Sidewalk Passerby (uncredited)
Arthur Tovey
Juror (uncredited)
Barry Kelley
Police Chief Oscar C. Brockton
Maurice Manson
Dignitary
Bill Zuckert
Jury Foreman
Al Bain
Hood
Linda Brent
Derelict
Billy Curtis
Newsboy
James Dime
Hood
Chuck Hicks
Factory Worker
Eugene Jackson
Congregation Member
Michael Jeffers
Nightclub Patron
Dick Johnstone
Club Patron
Larry D. Mann
Workman
Francis McDonald
Old Man at Robbo's Club
Boyd 'Red' Morgan
Jakes
Manuel Padilla Jr.
Orphan Boy
Frank J. Scannell
Robbo's Lawyer
Charles Sherlock
Pool Game Spectator
Richard Sinatra
Gisborne's Hood
Larri Thomas
Dancer
Al Wyatt Sr.
Hood