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