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