Every stunning hero requires an equally prodigious antithetic. Those profound villains etched in our memory are those that usher a difference, authenticity, and excitement to the narrative. Now, what is that common factor that binds The Joker, Two-Face, and Chance? The answer lies beyond being classic comic book super-villains – they are all united with their collective obsession for gambling. There exists a myriad of villains from DC Comics and Marvel that express their penchant for gambling. Maybe because gambling embodies their ambivalent and changing nature when juxtaposed to the stability of the superheroes, these comic books have left an enduring legacy of captivating stories and intriguing characters that everybody loves to loathe. 
The Joker
The famous enemy of Batman, according to him the stature of being the first super-villain that Batman encounters in the first comic book of Batman in 1940 – published by DC Comics. More than his fondness for gambling, what presented him with this name is the disfiguration that accorded him with the name of the joker from the playing cards. The fascinating facet is the way he commits his crime, and this includes a melange of thematic weapons, including a deck of razor-tipped playing cards and Jack-in-the-boxes with vicious surprises.
Two-Face/Harvey Dent
The fictional super-villain and antithesis of Batman – Two-Face. His alter ego is Harvey Dent, the popular District Attorney of Gotham, who has always relished a fancy for gambling. Though the narrative about Dent getting the left side of his face ghastly scarred remains ambiguous with numerous versions, he ultimately transforms into Two-Face. He is a criminal whose rationale for his evil acts is based on a coin flip. It is this famous coin flip that decides the destinies of Batman, Jim Gordon, and his son.
Chance
The nemesis of popular hero Spider-Man; had his first appearance in the Web of Spider-Man that was published by Marvel. The alter ego of Chance is Nicholas Powell, who is an affluent man and a seasoned gambler – who decides to transform his boring life into an exciting one by becoming a criminal-for-hire. He gratified himself by making work thrilling for him, and this was by viewing his job as a gambling game – if he was unsuccessful, it meant he lost the bet, and he would pay the people who hired him. He would receive payment only after having accomplished his mission.
The Penguin
The most tenacious antagonist to Batman is Oswald “Penguin” Cobblepot – a gangster and thief in the alluring world of DC Comics. He owns a casino known as “The Iceberg Casino,” the popular hangout for the underworld of Gotham. A floating legal casino, but Penguin never abandons his adulation for criminal life and, therefore, involves in the transaction of illegal information. This casino represents a haven for his fellow criminals to gamble, drink, and strategize their horrendous crimes while he reaps a bountiful harvest of money.