Four Comic Book Villains Who Love to Gamble

In order to have the complete pantheon of comic book characters, a cruel yet charismatic villain is essential. We want someone who we love to hate, but who’s complex enough to still evince some small amount of sympathy. They have to be boorish but believable, horrible but with a humorous wit that has us not wanting to see the back of them. And they have to be placed in context. They need cronies and sets that make them jump off the page as a fully formed person, and one place that every good bad guy loves to hang out is the casino. From the Joker to Two-Face, the Penguin to Chance, here are four villains who really enjoy a flutter.

The Joker 


Source: Facebook via The Joker


One of the most infamous on-page villains of all-time, The Joker is evil, effervescent, and absolutely obsessed with gambling. The Captain Hook to Batman’s Peter Pan, he’s been gracing the comic book sphere since his introduction in 1940, and we’ve loved to hate him ever since. But when do we actually see him game? The interesting thing about The Joker is not that he spends his days tucked away in gambling dens, but that his very name comes from the joker playing card, which he ends up resembling after being disfigured. Tying into this theme, he uses clever weapons like razor-tipped playing cards, a toxin known as the Joker Venom, and murderous Jack-in-the boxes to carry out his crimes – the imagery is strong here!


Two-Face/Harvey Dent 


As the super-villain enemy of Batman, Two-Face nonetheless has an ordinary alter-ego known as Harvey Dent. By day masquerading as an attorney, he’s shown to have a passion for betting – one that we see over and over. What’s more, following an incident in which he ends up hideously scarred, he transforms into a criminal who bases all of his evil acts on the outcome of a coin flip. It’s fair to say the writers at DC must very much enjoy a villain who places his trust in fickle fortune.


The Penguin


Source: Facebook via The Penguin


Now for a really obvious one: The Penguin. A bona fide mobster and thief, this awful enemy of Batman is the owner of The Iceberg Casino – hangout of choice for the criminal degenerates of Gotham. Although the casino itself is entirely legal, and likely has a whole host of slot and table games for punters to choose from, it nonetheless acts as the perfect cover for the villain’s more illegal operations, like the exchange of information and sale of stolen goods. Though the real-world new trend is for smaller bonuses like free spins, we’re not entirely sure of how invested the mob boss is in drawing in legitimate customers. That said, the casino always seems to be filled to the brim, so maybe The Penguin makes like his real-life counterparts and has more business savvy than we give him credit for.




Last but not least on our list is Chance, the long-time enemy of popular superhero Spiderman. His alter-ego is – appropriately – Nicholas Powell, a well-off professional gambler who tired of his ordinary life and transformed into a criminal-for-hire instead. Since he’s such a fan of dicing with fortune, he comes up with a unique proposition for his clients: if he’s successful in completing his mission, they pay him, but if he fails and thus ‘loses the bet’, he pays them. This way he gets all the thrill of gambling, with the added excitement of his criminal activities thrown in for good measure. We guess some people will do anything for an adrenaline rush! Even his name fits.


Which of these villainous chancers do you most love to hate?



3 thoughts on “Four Comic Book Villains Who Love to Gamble”

  1. I am a Joker fan. Through and through. The greatest villian of all time. Hands down, imo. The characters sheer lack of a compass of any kind, the absolute chaos he bestows upon the world, is what draws me to him. I relate to his devil may care attitude.
    Am I missing something, is Nicholas Powell supposed to be euphemism or something like that? Or were you simply referring to the name ‘Chance’ as apt?

  2. I’m on the coin flip team. I’ve always been intrigued by the tug-o-war within one’s self. The eternal struggle for dominant control over ones existence. The Dr. Jekyll and Mr Hyde, Dr. Banner and the Hulk…. essentially the Man and the Monster within. Two-face has all the potential to elevate himself to the top of the rogues gallery, if not for his dependence on fate. If he was to follow through on his devious plots rather than “chance it” he might complete his evolution. But however small, there is still some Harvey Dent in there. And always at the most inopportune time, Harvey’s throwing a monkey wrench into the works.

    Two-face is measured, methodical and mostly lacks empathy. Once he commits to a plan he’s hellbent on seeing it through. And yet at times, he’s his worst enemy. His dependence on fate and the few emotional “chinks in his armor” that triggers Harvey Dent to the surface are just as brutal to his schemes as an ever dependable flying bat-boot to the face.

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