The gambler follows a card (or dice) theme, uses cards, dice, darts, coins and gambling implements as weapons, and is very well-versed in blackjack, poker, craps, and all sorts of casino games. They rely much more on luck and cunning than on skill and outright power, and very seldom take it too hard on the occasions they lose, usually due to believing it was due to chance.
They tend to be slick, either elegant or gaudy, just like professional card players from the past, and are more towards lean and nimble than strong and resistant. Due to their very nature, they tend to fit the definition of tricksters, and one would be hard-pressed to find a particularly slow-witted person, or a grunt, in the position of the Gambler.
The entire theme around the gambler makes him usually either an Anti-Hero or an Anti-Villain, due to a view that they usually revere luck and chance over pledged allegiances, and that they will usually be too chaotic to be too specifically good or evil, Joker being a rather brutal exception to this rule. This trope is almost entirely populated by men, and it has been increasingly common as time goes by. See also: Death Dealer (using playing cards as weapons), as well as Born Lucky and Winds of Destiny, Change (when the character has actual powers over luck).
For actual gamblers, see The Gambling Addict or Professional Gambler.
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Anime and Manga
The Gambling King from Ranma ½. He even has the same face as one of the king cards.
Subverted - the Gambling King is an idiot who can only win against small children and the feeble-minded (i.e., Soun, but also Ranma, who can't keep a poker face to save his life.) Even then, he can only win by cheating, either through time-honored methods like hiding cards up his sleeves, to ceiling-mounted mirrors to spy on his opponent's hand, to using a motorized chair to drive behind his opponent and spy their cards from up close. Like Ranma, he is completely unable to keep a poker face. He's also fat, pudgy, as far removed from "elegant" as one can be, can hold deep-seated grudges, and hold small children responsible for upholding matters of honor.
The "holding grudges" thing isn't really as bad as it sounds, though. Considering that he, a GROWN MAN, was tied up and kicked off a bridge by two six-year-olds, it would be a wonder if he didn't harbor some ill will toward Ranma and Ukyo.
Ranma and many other characters was suffering idiot ball that entire story arc.Ranma was perfectly capable of playing shown in all the stories beforehand against his 2 school friends and other people.Seriously thinking someone that can't keep a straight poker face is able to learned Umi Sen Ken and able to manipulate strangers (who're at least average intellect) is beyond outrageous. Additionally Ranma was not the only one to acquire the idiot ball considering the Gambling King also managed to beat Nabiki.
Kaitou Kid from Detective Conan sometimes uses a gun (mostly in his own series, Magic Kaitou) that fires out razor-sharp playing cards.
That said, his day job is a magician.
Duke Devlin in Yu-Gi-Oh! follows a dice motif. Joey's deck gradually accommodated a few chance cards to balance his lack of powerful cards. There were a few times where either luck was not in his favor, or it was to the opponent's benefit.
One duelist who appeared in the second season of Yu-Gi-Oh! GX (who called himself "Boy" in the original, and "Pierre" in the dub) seemed to be so good at gambling that he drew a royal straight flush while playing poker. However, in Duel Monsters, he wasn't very lucky at all, needing a card that gave him a two chances at a coin toss in order to use any card that depended on chance.
Yugi's grandfather was also said to be a very lucky gambler when he was young, rarely losing. After winning every game of chance he knew of, he made a bet with himself that if he ever lost one, he'd retire, open a store, and wear overalls for the rest of his life. (Obviously, he eventually lost.)
Charlie McCoy in Yu Gi Oh Zexal was a duelist with cards that relied on chance, but had a rather unfair advatage: a Number card that gave him supernatural luck. He lost after Yuma discovered the clause that broke the spell it bestowed on him.
Tubalcain Alhambra from Hellsing OVA and manga is a vampire whose powers revolve around razor-sharp playing cards.
Hisoka in Hunter × Hunter is first seen using playing cards to cut people with. When he has to go all-out against stronger opponents later in the series, we see him fighting using sleight of hand to trick his opponents.
Rein Sunamoto from Best Student Council, who serves as a member of the assault squad but fights by throwing playing cards. She once took out a basement full of paparazzi with them.
Also Rein's father, a traveling gambler who abandoned Rein at a young age, and who uses playing card sleight-of-hand to talk a troubled mother out of making the same mistake he did.
The aptly named Gambit (pictured above), from X-Men, energizes playing cards to explode on impact and tosses them with precision at his targets. He could use anything if he felt like it (various incarnations have used chains, billiard balls, and an overturned bus), but playing cards are both convenient and stylish. The explosion is proportional to the size of the object, so cards, poker chips and other thematic objects are consistent and controllable.
The Joker, from Batman, subverts this trope quite a bit in that he usually only dresses like a joker, and in that he's a sociopath. He does use the occasional playing card gimmick, however.
While we're on Batman, there's Twoface, who does everything based on a coin flip. Also evil, though he is prone to flipback and forth at times considering his core gimmick and woobie backstory.
The DCU's Gambler is a Golden Age villain and Master of Disguise who gets by mostly on luck. His grandfather was a riverboat gambler and bandit, and the primary inspiration for his villainous turn. He committed suicide after losing at a rigged casino. His grandchildren, the second Gambler and Hazard, follow much the same gimmick, though Hazard has luck powers.
The Royal Flush Gang has always had a playing card motif, but not so much gambling... Except the Justice League version, who first appeared in an episode that took place entirely in Las Vegas. They were also Shout Outs to the Teen Titans.
100 Bullets has an entire story arc is devoted to a dice throwing conman named Chucky.
Marvel villain Chance is a mercenary who doesn't charge for his services-rather, he bets his fee against the odds of his success. If he fails in his mission, he pays his employer rather than the other way around.
In the Silver AgeDC Universe, two gambling aliens named Rokk and Sorban force Superman and The Flash to race to the edge of the galaxy and back, so they can settle a bet on which one is fastest. To keep things interesting, they imprison the rest of the Justice League, and promise to destroy the home city of the loser. (It turns out these are actually two of the Flash's arch-enemies, disguised as the aliens—who are back on their home planet betting on volcanic eruptions.)
An occasional Spider Man villain is Nick Powell, aka Chance. A high-demand Professional Killer who has become incredibly wealthy from his career, he not only loves to gamble, but has a unique way of billing his clients. He doesn't charge a fee at all, but rather wagers with a client against his success. To Chance, winning or losing a gamble really means nothing; it's the thrill of the gamble itself that matters.
Writer and producer Tim Burton and director Henry Selick's The Nightmare Before Christmas has Oogie Boogie, who is shown to base his actions off the roll of a die when torturing his captives. He also has a couple of game-based traps in his dungeon: a giant spinning roulette platform, monolithic cards with swinging swords, and the base of spinning propeller blades resembles an 8-ball.
You forgot about the actual one-armed bandits. Complete with guns.
Sort of subverted in that he's the most unambiguously evil in HalloweenTown.
Ace, one of the gunfighters in the Quickdraw Tournament in The Quick And The Dead, is this, mixing card motifs, gun tricks, and lots of pompous boasting.
Matrim Cauthon from the Wheel of Time, a compulsive gambler famously known for his luck that when he becomes a general dice are on his standard.
Mat is almost a subversion of this, noting that he's so supernaturally lucky that games of chance don't really qualify as gambling. He's naturally pretty good, but a side effect of his Weirdness Magnet trait ramps this Up to Eleven, so much so that none of his friends will play cards or dice with him.
Le Chiffre from about all versions of Casino Royale is something of a mathematical genius who uses his smarts to gamble about. It's when this doesn't work out so well for him that Bond steps in to deliver the killing blow.
Live Action TV
Pro wrestling example (though perhaps more of a subversion): WCW had The Gambler, a generic-looking wrestler whose only references to his alleged gimmick were 1) a satin ring jacket with "The Gambler" embroidered on the back, and 2) playing cards that he flashed at the camera before his matches. In later years he upgraded his ring attire, actually dressing as a riverboat gambler, but his perennial jobber status kept him from portraying the character with any more depth than that.
Before The Gambler was Vinnie Vegas, who wrestled in WCW in 1992, using a finisher called Snake Eyes which The Undertaker still uses to this day. Vinnie was briefly part of Harley Race and DDP's stables before leaving WCW to become...Diesel.
Third edition Dungeons & Dragons has the Fatespinner and Luckstealer prestige classes. Both require training in the Profession (gambler) skill and both have class features that revolve around manipulating the players' and DM's die rolls (increasing or decreasing the difficulty of rolls, or simply forcing retools).
Sin-Eaters of the Forgotten Threshold, having been offered their Bargain on account of their death by random chance, often pick up a gambling motif. That "the Curse" is one of the common Manifestations available to all Sin-Eaters is just icing on the cake.
Setzer, from Final Fantasy VI uses cards, dices, darts and slots in his attacks. His airship is named Blackjack. And he joins the party by losing a (rigged) coin toss. This clip shows how badass a Setzer can be: he's a wispy, Silver-Haired Bishōnen that sails his airship at top speed, unfazed by the wind as he stands at the rudder, who destroys a heavily-armed gunship by tossing a few sharpened cards at it. Ante up, indeed.
Final Fantasy VII has no distinct character classes, but Cait Sith can be considered a Gambler for the fact that his two Limit Breaks are based on rolling dice and spinning a slot machine, respectively.
In Final Fantasy X 2, the Lady Luck Dressphere grants the equipper gambling-themed abilities.
Final Fantasy XI has Corsairs, who are gambler pirates. Word Of God claims that they went this route due to market research revealing that gambling has a negative connotation in the US. Their Phantom Rolls boost specific stats by random amounts, and can be improved through a blackjack-like mechanic.
And the Trickster class in Final Fantasy Tactics A 2, who throw playing cards and use magic chants to, for instance, convince opponents that they've been poisoned (which is the same as poisoning them). The tricksters fought in the mission to unlock the class are all dimwitted thugs, though.
Oswald of The King of Fighters uses playing cards to cut his opponents. The names of his special moves are the names of suits and some cards. The name of his Leader Desperation Move is Joker, and one of his special moves hits, ideally, 21 times (an important number in blackjack, a card game). Furthermore, his color scheme is the one of playing cards: Black suit, red shirt (not that kind of red shirt) and glasses, white hair, and yellow tie for the details in the figure cards.
Just to drive the Gambler point home, he has a move called Ace that could either do very little damage and expose him terribly to his enemies, or done right, end with these.
This even extends into the game's soundtrack: "Joker" is the New Hero Team's theme (Oswald is on this team, by the by), "Queen" is the Rival Team's Theme, "King" is Adelheid's theme, and "Jack" is used for some sub-bosses.
Sneff, from Chrono Cross, throws playing cards at his opponents, and two of his moves revolve around playing cards: Big Deal, in which he tosses an entire deck, and HP Shuffle, in which he shuffles the three numbers that make up his HP (091 might become 910, 901, 190, 109, 091 and 019).
What's odd about Kyosuke's luck is it's mostly a plot-centered mechanic: it only kicks in during scripted events, and isn't a game mechanic like the "Luck" Spirit Command* Doubles money earned for one attack, doesn't really fit this theme or the "Lucky" pilot skill* When activated, the character automatically evades or makes a critical hit, regardless of normal chance to hit other characters carry.
Haken Browning from Spin-OffEndless Frontier makes up for every card and gambling pun Kyosuke didn't get to make. His attacks have names like Texas Hold'em, Five Card Stud and Jackpot, uses exploding cards in some of his attacks and his Overdrive involves switching his gun to "Klondike Mode". Unlike Kyosuke, however, he apparently cheats: one of his exclusive accessories is called "Loaded Dice".
Joshua in Fire Emblem 8, though he just has no luck at it. And he's a swordsman, so he doesn't use cards or such.
Although he is a swordsman in a class which specializes in critical hits, aka luck, in terms of actual gameplay mechanics.
Also we don't get to see much of his gambling luck; he knows how to cheat very well, even using normal coins.
In Path of Radiance is Makalov, whose only interests are gambling and doing as little work as possible.
Genjuro Kibagami of the Samurai Shodown series of fighting games uses gambling as his sole source of income. He is, apparently, an avid player of Hanafuda, and cards from the game figure heavily (though it would seem figuratively, at times) into many of his moves.
Kingdom Hearts II - Luxord, the Gambler of Fate fits this trope to a T. He uses cards and his power to control time to engage Sora in a very unorthodox time-based battle. He also possesses an advanced vocabulary and a classy British accent, which give him an air of sophistication.
The same goes for the Nobodies under his command - the appropriately named Gamblers.
The Juggle Pup dream eater in Kingdom Hearts 3 D is a lesser example of this, rolling a die for one of their primary attacks, which will then proceed to attack a random target (Be it friend or foe) based on which side lands face up..
One of the three semi-final bosses of Shadow The Hedgehog is an Eggman robot called the Egg Dealer, which selects its attacks slot-machine style... a fact that can easily be turned against it.
Eggman actually does this a lot. In Sonic X, he had all of his robots on cards, which he then stuck into a slot machine to pick which one to use. Also note that every single one was situation appropriate, and this was practically Once an Episode.
In Knuckles' Chaotix, Metal Sonic first fights by inserting himself into a large roulette nearby (which is normally used to pick stages to visit next). Four of the five spaces cause weapons to come out and attack the player character if the roulette lands on any of them, with the fifth disabling one of them. You have to disable all four weapons to defeat him.
A custom car set in a Need for Speed title has the four aces as a paint job.
Ronfar from Lunar Eternal Blue uses dice and cards in some of his special attacks. Interestingly, he used to be a priest before indulging in games of chance.
Nero from Devil May Cry 4 has several moves named after gambling terms (Double Down, Maximum Bet, Roulette Spin, High Roller), so he could technically count. Plus, he's the only one who has to play that damn dice game...
Tai Ho, member of the 108 stars of destiny in the first two Suikoden games. An unapologetic Deadpan Snarker, you must prove your luck to him via gambling in order to advance the plot of at least one of the games, and in the second game you must beat him at gambling in order to recruit him.
Patty Fleur, of the Tales Of VesperiaPS3 remake, uses many luck based skills and attacks, most notably her Mystic Arte, where you have a chance to heal everyone, max out everybody's overlimit, or summon Barbatos to destroy just about every enemy on field, amongst many other things. Also notable the it takes on the look of a gigantic roulette table with poker chips all around.
King Boo seems to have a love of gambling. In his debut in Luigi's Mansion the keys to the various parts of the mansion have playing card suit motifs. Later, in Super Mario Sunshine, he hides in Hotel Delfino's casino, where he battles Mario while holding a water-powered slot machine that can summon enemies, coins, or fruit.
In Left 4 Dead, Nick used to do this before the infection hit.
In the MMORPGDofus and its sequel Wakfu, the Ecaflip class is a based partially around gambling (with attacks that involve throwing cards or rolling dice, and spells that have completely random effects), partially around their feline nature. The class symbol is a single die in Dofus and a pair of dice in Wakfu, and their special class outfit is decorated with playing cards and card suits (including a cape that's just a giant ace of spades). Even their name is the French for "heads or tails" backwards.
Johnny from Guilty Gear is one. He attacks using coins and his Instant Kill move turns the opponent into a Joker card before he slices them in half. Additionally, some of his move names have a gambler motif to them.
Twisted Fate of League Of Legends is an assassin with abilities named after gambling terms, many gambling-related quotes, and throwing cards as his primary weapon. One of his signature abilities is picking between three cycling colored cards to determine his next attack's effect. His ultimate ability shows the opponent's hand, so to speak, by revealing all enemy locations and allowing him to teleport a huge distance to either ambush a lone foe or escape from impending danger.
Mega Man Star Force 3 features as its main villains a criminal syndicate named "Dealer". It is led by one Mr. King, and has among its high-ranking members Queen Tia, Jack, and Joker. Furthermore, three of the (unwitting) major bosses of the game are Spade Magnes, Diamond Ice, and Club Strong, while King's Dragon is named Heartless. None of them really use playing card motifs in battle, but they do get bonus points for having their base's inner sanctum decorated like a gigantic card table.
Tetras in The Motley Two (a fanfic of sorts of Homestuck), a descendant of Homestuck's Vriska, as described above. She also uses Wild Magic dice as weaponry, though her IMPERIAL DUET has powerful effects with both extremely low and extremely high rolls. Which is good, since she's unlucky and tends to roll low.
Poker-Face, from Silverhawks. His weapon is a staff that releases a card-suit shaped laser. His eyes are slots that change to match the occasion ($ signs when thinking about money, for instance).
Wait...if they change to match what he's thinking about, doesn't that actually defeat the point of a poker face?
He wore sunglasses, which may just lead to further questions.
In one episode of Jackie Chan Adventures (specifically, an episode parodying the James Bond series), Dr. Necrosis' Dragon had power over playing cards, and always spoke in metaphors and puns related to them. "The deck is stacked in our favor! We have the upper hand!" "Dealer calls a new game!" "I thought he folded..."
Ezekial Clench of Samurai Jack was a Wild West style villain with a slight playing card motif; The spurs on his boots were shaped like spades, he had a card in his hat... Oh, and his cybernetic hands, the wrists of which had the playing card suits on them. The hands had a special ability depending on which suit was facing up. He's also a bounty hunter, and on the run from his ex-wife, so luck is a big deal to him.
On Batman Beyond, the Royal Flush gang were a villainous team example.