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Fictional crime bosses

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The Joker
fictional character throughout the DC Universe
Vito Corleone
fictional character from Mario Puzo's 1969 novel The Godfather
Professor Moriarty
fictional character from Sherlock Holmes
Darth Maul
fictional character from the Star Wars universe
Two-Face
Two-Face is a supervillain appearing in American comic books published by DC Comics. The character was created by Bob Kane, and first appeared in Detective Comics #66 (August 1942). He has become one of the superhero Batman's most enduring enemies belonging to the collective of adversaries that make up his rogues gallery.
Lex Luthor
fictional character in DC Comics
Riddler
The Riddler (Edward Nigma, later Edward Nygma or Edward Nashton) is a supervillain appearing in American comic books published by DC Comics. He was created by Bill Finger and Dick Sprang, and debuted in Detective Comics #140 in October 1948. He is one of the most enduring enemies of the superhero Batman and belongs to the collective of adversaries that make up his rogues gallery.
Boba Fett
fictional character in Star Wars
The Penguin
supervillain appearing in DC Comics publications and related media
Walter White
fictional character in the television drama series Breaking Bad
Kingpin
fictional character in Marvel Comics
Ra's al Ghul
fictional character, a supervillain who appears in comic books published by DC Comics
Jabba the Hutt
fictional character in Star Wars
Bane
fictional character in the DC Comics universe, a supervillain
Michael Corleone
fictional character from The Godfather series
Black Cat
fictional character in Marvel Comics
Deadshot
Deadshot is a supervillain appearing in American comic books published by DC Comics. Created by writer David Vern Reed and artist Lew Sayre Schwartz based on a concept from Bob Kane, the character first appeared in Batman #59 (1950). Introduced as a gun-toting criminal in a tuxedo, top hat, and domino mask, Deadshot was only intended to be a one-off villain for the superhero Batman, but writer Steve Englehart and artist Marshall Rogers revived, redesigned, and popularized the character in Detective Comics #474 (1977), which featured the debut of his wrist-mounted guns, reticle emblem, and mask
Ernst Stavro Blofeld
fictional James Bond villain
Tommy Vercetti
protagonist of the 2002 video game Grand Theft Auto: Vice City
Tony Montana
fictional character from Scarface
Jesse Pinkman
fictional character of the television drama series Breaking Bad
Trevor Philips
protagonist of the 2013 video game Grand Theft Auto V
Sonny Corleone
fictional character from The Godfather series
Mad Hatter
fictional character in DC Comics
Hobgoblin
fictional character in Marvel Comics
Shredder
fictional Teenage Mutant Ninja Turtles character
Fu Manchu
supervillain in a series of novels by the English author Sax Rohmer during the first half of the 20th century, based off ethnic stereotypes
Fat Tony
fictional character from The Simpsons franchise
Emma Frost
fictional character in Marvel Comics
M. Bison
video game character created by Capcom
Jason Todd
fictional character in DC Comics
Tony Soprano
fictional character from The Sopranos
Tommy Shelby
fictional character from Peaky Blinders
Gus Fring
character in the television series Breaking Bad and Better Call Saul
Rastapopoulos
Roberto Rastapopoulos is a fictional character who is a featured villain in several entries in The Adventures of Tintin, the comics series by Belgian cartoonist Hergé. He first appears in Cigars of the Pharaoh (1932) and is a criminal mastermind with multiple identities, whose activities frequently bring him in conflict with his archenemy Tintin.
Ventriloquist
enemy of Batman in the DC Comics Universe
Black Mask
supervillain and mob boss appearing in comic books published by DC Comics
Carmine Falcone
fictional character appearing in DC Comics
The Joker
Character from the 2008 film The Dark Knight
Hammerhead
fictional supervillain (Marvel)
Vincent Corleone
fictional character from The Godfather series
Tombstone
fictional character in Marvel Comics
Emilio Barzini
fictional character from The Godfather series
Mister Negative
fictional character in Marvel Comics
Calendar Man
comic book character
Arlong
REDIRECT List of One Piece pirates#Arlong
Alex
fictional character in A Clockwork Orange
Rupert Thorne
Fictional character in the DC Universe
Keyser Söze
character in the 1995 film The Usual Suspects
Alec Trevelyan
Bond Villain
Bib Fortuna
character in Star Wars
Junior Soprano
fictional character from The Sopranos
Giorno Giovanna
fictional character from JoJo's Bizarre Adventure
Shadow King
fictional character in Marvel Comics
Jigsaw
fictional character in Marvel Comics
Moe Greene
fictional character from The Godfather series
Jax Teller
fictional character in the FX television series Sons of Anarchy
Hood
Marvel character
Owl
fictional character in Marvel Comics
Sal Maroni
fictional character throughout the DC Universe