This list also includes hitmen, bankrobbers, and thieves. Does not include western outlaws (such as Paul Newman and Robert Redford in Butch Cassidy and the Sundance Kid) nor serial killers (such as Woody Harrelson in Natural Born Killers).

Next to the name of the actors, are a film or two of which they are best remembered for, when playing a gangster/criminal.

B
Bela Lugosi (Black Friday)
Ben Kingsley (Bugsy)
Bill Graham (Bugsy)
Bill Murray (Quick Change, Mad Dog & Glory)
Bob Hoskins (The Long Good Friday, The Cotton Club)
Boris Karloff (Scarface (1932))
Brian Dennehy (Teamster Boss)
Bruce Willis (Last Man Standing, Whole Nine Yards)
Bruno Kirby (The Godfather Part II)
Burt Reynolds (Breaking In, The Crew)
Burt Young (Once Upon a Time in America, Mickey Blue Eyes)

C
C. Thomas Howell (Baby Face Nelson (1995))
Cary Grant
Charles Bronson (Machine Gun Kelly)
Chazz Palminteri (A Bronx Tale, Bullets Over Broadway)
Chow Yun-Fat (The Killer, The Replacement Killers)
Chris Penn (Reservoir Dogs, The Funeral)
Christian Slater (Mobsters)
Christopher Walken (King of New York, Last Man Standing)
Clark Gable (A Free Soul, Manhattan Melodrama)
Clint Eastwood (Absolute Power)

D
Dan Hedaya (Wise Guys)
Danny Aiello (The Godfather Part II, The Last Don I & II)
David Janssen (King of the Roaring 20's)
Dean Martin (Robin and the 7 Hoods, Ocean's 11 (1960))
Dean Stockwell (Married to the Mob)
Delroy Lindo (Clockers, Get Shorty)
Dennis Farina (Midnight Run)
Dennis Hopper (Backtrack)
Donald Sutherland (Great Train Robbery)
Douglas Fairbanks Jr. (Little Caesar)
Dustin Hoffman (Family Business, Billy Bathgate)

E
Ed Harris (State of Grace)
Eddie Murphy (Harlem Nights)
Edward G. Robinson (Little Caesar, The Little Giant, Key Largo)
Edward James Olmos (American Me)
Eric Roberts (The Lost Capone)
Ethan Hawke (Newton Boys)

F
F. Murray Abraham (Scarface (1983), Dillinger & Capone)
Faye Dunaway (Bonnie & Clyde)
Forest Whitaker (Diary of a Hit Man)
Frank Sinatra (Robin and the 7 Hoods, Ocean's 11 (1960))
Fred Gwynne (The Cotton Club)

G
Gabriel Byrne (Miller's Crossing, The Usual Suspects)
Gary Cooper (City Streets)
Gary Oldman (State of Grace)
Gene Hackman (Bonnie & Clyde)
George Bancroft (Underworld (1927), Thunderbolt)
George Clooney (From Dusk 'til Dawn, Out of Sight)
George Raft (Scarface (1932), Some Like it Hot)
George Segal (St. Valentine's Day Massacre)

H
Harvey Keitel (Reservoir Dogs, Bugsy)
Humphrey Bogart (The Petrified Forest, Dead End, The Roaring Twenties, High Sierra)

J
Jack Nicholson (St. Valentine's Day Massacre; bit, Blood and Wine)
Jack Palance (Panic in the Streets, I Died a Thousand Times)
Jackie Gleason (All Through the Night)
James Caan (The Godfather, Mickey Blue Eyes)
James Cagney (Public Enemy, Angels With Dirty Faces, White Heat, Love Me or Leave Me)
James Woods (Once Upon a Time in America, Another Day in Paradise)
Jason Priestley (Coldblooded)
Jason Robards (St. Valentine's Day Massacre)
Jean Reno (La Femme Nikita, The Professional)
Jeff Goldblum (Deep Cover, Mad Dog Time)
Jerry Orbach (The Gang that Couldn't Shoot Straight)
Joe Mantegna (The Godfather III, The Last Don I & II)
Joe Pesci (Goodfellas, Casino)
Joe Piscapo (Johnny Dangerously)
John Cusack (Grosse Pointe Blank)
John Leguizamo (Carlito's Way)
John Travolta (Pulp Fiction, Get Shorty)
John Turturro (Men of Respect, Sugartime)
Jon Polito (Miller's Crossing)

K
Kathleen Turner (Prizzi's Honor)
Kevin Costner (The Gunrunner)
Kevin Spacey (The Usual Suspects)
Kim Basinger (The Real McCoy, The Getaway (1994))
Kirk Douglas (I Walk Alone, The Brotherhood)

L
Lawrence Fishburne (King of New York, Hoodlum)
Lawrence Tierney (Dillinger (1941), Reservoir Dogs)
Lee Marvin (The Killers (1964))
Lee Strasberg (The Godfather II)
Leonard Nimoy (Star Trek episode: "Piece of the Action")
Leslie Nielson (featured as a convict in an episode of The Untouchables TV series, Dayton's Devils)
Lino Ventura (Boulevard du rhum)
Lloyd Bridges (Mafia!)
Lon Chaney (The Unholy Three)
Lou Diamond Phillips (The Big Hit)

M
Marc Lawrence (Lady Scarface, Hold That Ghost, Dillinger (1945), Gotti)
Mark Wahlberg (The Big Hit)
Marlon Brando (The Gofather, The Freshman)
Martin Sheen (Dillinger & Capone)
Matthew McConaughey (Newton Boys)
Michael Cain (Blood & Wine)
Michael Keaton (Johnny Dangerously)
Michael Lerner (Eight Men Out, Harlem Nights)
Michael Madsen (Reservoir Dogs, The Getaway, Donnie Brasco)
Mickey Rooney (Baby Face Nelson)
Mickey Rourke (Johnny Handsome)
Milton Berle (Lepke)

N
Nicholas Cage (The Cotton Club)
Nicholas Turturro (Witness to the Mob)

O

P
Pat Hingle (The Grifters)
Patrick Dempsey (Mobsters)
Paul Muni (Scarface (1932))
Paul Sorvino (Goodfellas, The Rocketeer)
Peter Boyle (Crazy Joe, Johnny Dangerously, Men of Respect)
Peter Falk (Crazy Joe, Johnny Dangerously, Men of Respect)
Peter Riegert (Oscar, Coldblooded)

Q
Quentin Tarantino (Reservoir Dogs)

R
Ray Liotta (Goodfellas)
Raymond Burr (Raw Deal (1948)()
Richard Conte (The Big Combo(, The Godfather()
Richard Dreyfuss (Dillinger (1973), Mad Dog Time, Lansky)
Richard Lynch
Richard Grieco (Mobsters)
Richard Pryor (Harlem Nights)
Richard Widmark (Kiss of Death (1947))
Robert Armstrong (The Racketeer)
Robert De Niro (The Godfather II, Once Upon a Time in America, The Untouchables, Goodfellas, Heat, Analyze This)
Robert Duvall (The Outfit)
Robert Mitchum (Out of the Past)
Robert Prosky (Thief)
Robert Redford (The Hot Rock)
Robert Shaw (The Sting, The Taking of Pelham One Two Three)
Rod Steiger (Al Capone, Men of Respect)
Ronald Reagan (The Killers (1964))

S
Sammy Davis Jr. (Robin and the 7 Hoods, Ocean's 11 (1960))
Samuel L. Jackson (Pulp Fiction, Jackie Brown)
Scott Baio (Bugsy Malone)
Scott Glenn (Verne Miller)
Sean Connery (Great Train Robbery, Family Business, Entrapment)
Skeet Ulrich (Newton Boys)
Spensor Tracy (Quick Millions)
Stanley Tucci (Billy Bathgate, The Public Eye)
Sterling Hayden (The Asphault Jungle, The Killing)
Steve Buscemi (Reservoir Dogs)
Steve Martin (My Blue Heaven)
Sylvestor Stallone (Capone (1975), Oscar)

T
Terence Stamp (The Hit, The Limey)
Tim Roth (Little Odessa, Hoodlum)
Tom Hanks (Fallen Angels)
Tom Sizemore (Heat, Witness to the Mob)
Tony Curtis (Lepke)

U

V
Val Kilmer (Heat)
Victor Mature (Gambling House)
Vincent D'Onofrio (Newton Boys)
Ving Rhames (Pulp Fiction, Out of Sight)

W
Walter Matthau (Gangster Story)
Warren Beatty (Bonnie & Clyde, Bugsy)
Warren Oates (Dillinger (1973))
Wesley Snipes (New Jack City)
William Forsythe (Dick Tracy (1990), Untouchables (TV Series))
William Shatner

X

Y

Z

If you do not see an actor/actress that you feel should be on this list, please let me know your suggestion.