Jack Purcell

Harry Stark

Mr. Wilkens / Alice's Father

Detective Cutchin

Detective Kelly

Rick Blaine

Lucas Bergman

Fortunato

Jail Inmate

Tom Goodwin

Lucas Bergman

Roscoe

Agent Tom Mason

Chaz Coleman

Detective Parker

Self

Detective Clayton Douglas

Jonas

Pluto

Marshal Steed

Hank

Mike Gillis

Scott Madison

Samuel Klein

Jace

Sheriff Walsh

Jeff

Dr. Oomious

Joe Salvatore

Cully

Moore

Self (archive footage)

General Reed

Thomas Winters

DEA Head Craig Ford

Mr. Wilkens

Preacher

Reggie

Colonel Mayweather

Pastor Dave Twiss

Lucky

White (archive footage)

Detective Frank Nitti

Callahan Wilson

Max London

Richard Gates

Sgt. Mason

Don Carlo

Property Owner

Al Unser

Father William

Coco Lewandowski

Dwayne Franklin

Colonel Forrester

Doctor Simon

Boyd Dennison

Detective Michaels

CIA Agent Terry Davis

Mr. Gilliam

Larry

Col. Big Rich

Nurse Walter Zanin

CIA Agent McKitrick

Detective Jake Dawson

Self

Self

Giovanni Moretti

Victor

Bill Sullivan

Phoenix

Mickey Duro

Detective Gary Broza

Bloodshed

Zek

Captain Vickers

Detective Frank Nitti

Eddie Green

John Sykes

Vincent Modine

O'Malley

Sergeant Mike Martin

McWhorter

Tony

Lavoie

Nick

Jon

Pedro

Roy

Kyle Norris

Jack Durant

Assemblyman Dean Bada

Dr. Richard Baum

Detective Mark Hume

Chief McClelland

Damian White

Mike Jones

El Viejo

Jeff

Orphanage Headmaster

Self

Howard Markby

Hamilton Markham

Knicks

Bob

Ricks

Timothy Bonner

Frank

FBI Agent Ridley

Bruce Frye

Randy

Glen

General Vincent Tate

Jimmy Marcos

Tom

Ernie

Sonny

Dean Ranson

Vito

Pickett

Mike Gillis

Leroy Lowe

Tom Kingsford

Frank Rossi

DEA Agent Sam Mathews

Tony 'The Hip' Anzaldo

Detective Frank Nitti

Doyle

Himself

Abel Cain

Col. Bunker

Craig

Roger Cheatem

God

Angelo Esposito

Michael McCormack

Large Bills

Price

Van Sant

Dale

Frank Miller

Max Walker

Ronnie

Himself

Burt

Vince Stoker

Steve

Armand Mehlman

Detective Cunningham

Tom

Pierce

Joey

Feedo

Self

Self

Kain Diamond

Dad

Pete Rose

Rex Harper

Lt. Owen Underhill

Tom Sizemore

Snake

Seith Georg

Tom Cherry

Zach

LTC Danny McKnight

Det. Ray Nettles

Earl Sistern

Dr. Quinn Burchenal

Les Fletcher (voice)

Joe Domino

Bobby Batton

Tom Wolls

Buffalo

Teddy Finn

Paulie Pintero (uncredited)

Sergeant Horvath

John Gotti

Lt. Vincent D'Agosta

Michael Cheritto

Max Peltier

DeWitt Albright

Det. Jack Scagnetti

Bat Masterson

Det. Danny Detillo

Cody Nicholson

Milo Peck

Danny

Jesse Meadows

Sly Delvecchio

Lenny

Eddie Hale

Zeno Stefanos

Chance Wilder

DEA Agent Deets

Ray Karlin

Boxman

Wool Cap

Vet - Villa Dulce

Mugger #2

Ian

Dallas