Chess with Death



"Death looked long and hard at the board. The abbot waited to see what long-term, devious strategies were being evolved. Then his opponent tapped a piece with a bony finger. he said, "

- Small Gods

A character gets into a contest of some sort with The Grim Reaper, Satan, or some other supernatural entity, usually with some dire consequence if the human loses. This is Older Than Feudalism, with examples dating back to Greek myths of the 5th century BCE - Apollo had at least one musical duel, the Muses had another musical contest, and Athena had a weaving contest with Arachne (the details vary between different versions, but the end result is that Arachne ended up being turned into a spider).

Note that the Greek Gods were prone to throwing tantrums if they were beaten and cursing the mortals for it - having the supernatural entity take a defeat on the chin could have originally been considered a subversion.

The most mimicked version is to have a dying man challenge The Grim Reaper to a Chess game in return for a longer life, hence the trope title. See also Enemies with Death and Smart People Play Chess. However, it doesn't have to be chess - if the player is allowed to pick the game, absolutely anything could happen.

Compare Did You Just Scam Cthulhu?.

Not to be confused with Human Chess where the pieces are humans and captured pieces are sometimes killed.

Comic Books

 * Used in one issue of Marvel Adventures: Avengers; the Avengers end up playing Human Chess with Galactus over the fate of an alien world. Hulk screws up and it's a stalemate, so they try in a human-scaled stadium baseball. Ant-Man screws it up, so they play poker. Hulk screws up again, and then Spider-Man mentions that he's hungry and they end up in an infinite-star restaurant.
 * The Marvel Comics cosmic villain, The Grandmaster, is obsessed with games, especially using humans as pawns. In one occasion, he challenged Death herself, in order to get back his dead brother. He won, but had to die in his place. This turned out, however, to be part of a larger Xanatos Gambit of his.
 * In Top Ten spin-off Smax, there is actually a specific Death responsible for playing chess with "wily peasants". His name is Lionel. Naturally, he even looks like the Grim Reaper in The Seventh Seal. Just as naturally, he isn't very good at chess (that's why the peasants always win).
 * In Grant Morrison's Seaguy, the eponymous hero plays chess with a none-too-clever, black-white colorblind Death.
 * Wait a second, being color blind means you see the world in various shades of black, white, gray. How is Death unable to distinguish between white and black? Wouldn't that just make him blind?

Film

 * Famously occurs in Ingmar Bergman's The Seventh Seal, pictured above. This is the origin of the "chess with the reaper" form of this trope.
 * Not specifically the origin: The Knight mentions that he has seen Death play chess on paintings; this is true, the motif of death playing chess exists as a motif in a Swedish church (although whether or not the game is chess or checkers or some other game is hard to make out)
 * Interestingly here Death isn't above cheating slightly. At one point he impersonates a priest the knight confesses his sins to, and mentions that he has a strategy that he is sure will beat death. So death (still pretending to be a priest) asks what it is. So the knight tells him. Death thanks him for the knowledge and leaves.
 * Neither is the knight. He tips over the chess board and claims not to remember where the pieces were. Death, however, has not forgotten.
 * Although the knight doesn't do this to cheat, he does it to distract Death so that Death won't see his friends slipping away.
 * This scene was lampooned in (500) Days of Summer, with Cupid replacing Death.
 * The Seventh Seal example is parodied in Bill and Ted's Bogus Journey, with our heroes besting the Reaper instead in games like Battleship, Clue, and Twister.
 * The multiple wins become a plot point in the novelization and comic adaptation, where the boys get killed several times during the final showdown with their Evil Twins and make Death bring them back each time by citing all the games.

Literature

 * In Thomas Bontly's Celestial Chess, the monk Gervaise played conventional chess against Satan and won the first two matches. Unfortunately, he then played the eponymous game in a Deal with the Devil. The twist is that Satan's pieces were indicated by planetary or stellar bodies in this variation; Gervaise knew enough astronomy that he thought he could predict all the possible responses to any given move. He didn't expect a supernova...
 * In Teresa Edgerton's The Grail and the Ring, Tryffin plays a series of chess matches with the king of The Fair Folk for the freedom of his party (not realizing, upon entering the series, that the local rules of the game are different from those with which he is familiar).
 * In the Discworld novels, Death is willing to play games for one's soul if it's requested of him, with the twist that he cannot be beaten by normal means. Many a chess grandmaster has expressed considerable annoyance with this, especially since he displays the handicap revealed in the above quote. (He can, as mentioned below, choose to lose if the situation is right.)
 * In the The Demonata series by Darren Shan, the first real scary scene has Grubbs' mother, dad and sister brutally butchered because they lost a game of chess against Lord Loss. The same book ends with Grubbs playing Loss in a game of chess for the same reason his parents did.
 * Terry Jones' The Saga of Erik the Viking has the eponymous character play Death to fulfill a bargain made earlier in the book for the life of one of his men. He was steadily losing, but Death was banished before the game ended.
 * One of the oldest written accounts comes from Geoffrey Chaucer's The Book of the Duchess, which features a knight who played chess with Fortuna (the Greek Goddess of Luck) for the life of his wife.
 * El-ahrairah from Watership Down.

Live Action TV
"Holly: Name me a game. Queeg: Chess. Holly: It can be anything at all. Queeg: Chess. Holly: Draughts, poker, any game at all. Queeg: Chess. Holly: Subbuteo, Snakes And Ladders, you name it. Queeg: Chess. Holly: Monopoly, maybe? I'll let you go first. Queeg: Chess. Holly: So you like a bit of chess then, do you?"
 * The opening to The Colbert Report's "Cheating Death" segment shows Stephen Colbert tricking Death into looking away, then rearranging the pieces.
 * Red Dwarf's Holly challenges the usurper Queeg for the right to be the control computer aboard ship.

"Death: Checkmate? Bollocks to this!"
 * Holly is duly walloped in the game (judging by the number of "prawns" and "horseys", he probably never knew how to play) and deleted, until...
 * Parodied in Big Wolf on Campus, in which the eponymous character's knowledge of the trope causes him to impulsively challenge Death to a game of chess, or as he calls it, "the one with the towers and the horsies... right?" Naturally, he loses, but does manage to convince Death to play another game of checkers, and loses. Then Battleship, loses. Then Candyland (which he was master at). By the time they try to pull out Barrel of Monkeys, Death's had enough.
 * There's a VERY good chance they'd seen Bill and Ted's Bogus Journey which parodies it in the reverse way.
 * In Lexx, the undead Kai plays chess to win back his soul... but his motivation isn't to rejoin the living, but to finally, properly die.
 * His opponent is Prince, who is either Death or the Devil, or both.
 * The Young Ones: The episode "Nasty" starts with a direct homage to The Seventh Seal, where Death loses. Then kills his opponent anyway.

"Xander: If Death ever tries to challenge you to a game of Chess, don't. He's some kind of whiz."
 * Buffy the Vampire Slayer lampshades this trope.

Music

 * Starflyer 59's "No New Kinda Story" music video is a very clear Shout-Out to Bergman's chess match. (Although the hooded figure could be interpreted as God instead of Death; the video is something of a Mind Screw.)
 * Russian band "King and Jester" has a song called "Henry and Death" in which Henry the King, a chess prodigy, defeated every worthy opponent in his kingdom and decided to challenge the Death itself. He loses due to death knowing each his move in advance.

Tabletop Games

 * One of the 50 game scenarios, called Haunts, in Betrayal at House on the Hill, has players attempting this trope. Players can cheat though, as one player can stay for the game, and others can run around the board finding items that help the chess-player cheat and hopefully defeat Death.
 * One Duel of the Magi or some such book (one of the few gamebooks ever designed for PVP) featured the player being able to help out a potential ally in a chess game for an extra year of life. If she survives, you get a place to rest, and some special equipment.

Video Games

 * The player in A Fine Day for Reaping must win a chess game (or otherwise convince the person to move on) to reap one soul.
 * Except the player doesn't play any chess, this being Interactive Fiction, and your character isn't very good at it. You have to read an encyclopedia to beat the person at chess, in fact.
 * The premise of Umineko no Naku Koro ni is the main character getting trapped into playing a chess game (Although the way it plays out looks more like 13 Dead End Drive) with a witch - with one big catch - it's Human Chess with his family as the chess set.
 * It's also nothing like chess.
 * In The Sims 3, you could challenge the Grim Reaper to a game of chess in order to save someone's life. He/she better be damn good at chess.
 * The "Chess Event" against Medivh in Karazhan. Failure to win the game results in the players' deaths. Medivh cheats.

Web Comics

 * In Casey and Andy, beat the devil at chess to undo selling his soul was part of Quantum Cop's Gambit Roulette to defeat Quantum Crook in one Story Arc.
 * Parodied in the webcomic Life and Death, in which nothing is at stake but Death still wins every game. He does, however, have one weakness.
 * Death and The Maiden: Death's not very good at board games, but it's still not a good idea. He got so sick of challengers that he beat one to death with the chess board.
 * Also parodied in Life and Death (not to be confused with the above) as Steve (Death) has anger management problems when he loses. And for goodness sake, don't try it with pool.
 * This Dawn of Time strip features an unconventional gambit.
 * Truck Bearing Kibble has this variation.

Western Animation
"Professor Monkey-For-A-Head: I challenge you to a game of chess! Death: *bored sigh* Alright, alright, union rules state I must take your challenge. What do you want, white or black?"
 * Earthworm Jim:


 * And in true Discworld style, neither of them know what "the little horsey guys" do and they decide to just flip a coin instead. Death wins (he used a two headed coin) but it turns out to be All Just a Dream (the episode where this happens is a parody of The Wizard of Oz).

Anime and Manga

 * In the Hentai OVA Ane Haramix, a female shinigami comes for the protagonist's life but reveals out of pity that shinigamis have a secret rule: if a human sires a child, his lifespan is extended by several years. Thus, he sets out to impregnate the only girl he knows well, who turns out to be his sister, so things get complicated. One Thing Led to Another, and in the end both his sister and the shinigami end up pregnant, at which point the other rule is revealed: if a human sires a child with a shinigami, his lifespan is extend way beyond natural one.
 * At the climax of Summer Wars, Natsuki takes advantage of the fact that Love Machine treats everything as a game and played several matches of Koi-Koi with it. Several Crowning Moment of Awesome/Heart Warming later, she managed to make a mere card game look epic and won back the millions of stolen accounts. If she lost? A missile-powered satellite will crash into a nuclear power station around the world and... yeah.
 * During the game chapters/episodes of Haruhi Suzumiya, notably the baseball and Day of Sagitarius episodes, if the SOS Brigade lost either of these games, Haruhi would become infuriated (and, if known liar Koizumi can be trusted, end the world).

Comic Books

 * In one issue of Ghost Rider, Ghost Rider races against Death for the lives of a man, a little girl, and himself.
 * Jack from Fables played cards in a louisiana swamp with the devil in disguise. At first it seemed like the devil had the upper hand and when Jack had nothing left to bet he offered up his soul, but only if the devil would give him his Bag of Holding the devil agreed and Jack won, having had four of a kind the entire time and simply waiting til the devil was cocky enough to bet the sack.
 * Groo the Wanderer once had a sword fight with Death. Groo won.
 * The Flash has escaped Death by beating him in a race on numerous occasions.
 * One man has the audacity to play Lawn Darts with Death. That man is Flaming Carrot.
 * Wolverine has at times engaged in battle with Lazaer, the Angel of Death, for the right to return to his body.
 * In the MarvelMAX Destroyer miniseries, the eponymous character is allowed to come back after winning a fistfight against several reapers.

Film

 * Parodied in Bill and Teds Bogus Journey. They don't play The Grim Reaper at chess... instead they beat him at Clue, Battleships, Twister... Eventually the Reaper gives up and joins them.
 * The climax of the 1986 film Crossroads is a guitar battle between Eugene and Jack Butler (the Devil's chosen one) for Willie Brown's soul. Eugene wins.
 * Pirates of the Caribbean: Will Turner's game of Liar's Dice against Davy Jones, pitting his soul against the key to the Dead Man's Chest. In the spirit of the game itself, the trope is subverted - all Will really wanted was the key's location, so he could steal it later.
 * Interestingly enough, he technically loses, but just as Jones is starting to gloat -- "Welcome to the crew, boy..."—Will's father ups the bet so as to save Will.
 * Fritz Lang's Der Mude Tod, also known as Destiny, revolves around a woman trying to meet Death's challenge to save one of three people's lives in order to get her husband back. When she fails at that, Death asks for another soul in return. When she refuses to give him a baby trapped in a fire, Death takes her instead. Bergman cited this film as an inspiration for The Seventh Seal.
 * In the short film De Düva (U.S. title The Dove), 1968. Despite the name the film was made in the U.S. Death is challenged to a game of badminton "badmintonska", and loses. The film was nominated for an Oscar (short subject), but didn't win. Perhaps the director should have challenged the Academy to a game of badminton!

Literature

 * In Samuel Taylor Coleridge's The Rime of the Ancient Mariner, Death and Life In Death gamble with dice, and Death wins the crew, while Life In Death wins the Mariner, and gives him a Fate Worse Than Death.
 * In the Discworld series, Death is often challenged to these. Again, with the twist that he can't lose (unless he wants to). For example:
 * In Maskerade, Granny Weatherwax challenges Death to a poker game for the soul of a dying child, with the stakes being that if she wins he'll instead take the sick cow in his place (but if he wins, it's double or nothing; Granny has to put her own life on the line as well). Granny initially tries to cheat, but Death insists they exchange hands. Granny has four queens—and Death admits defeat, having "only " (Death, in addition being a pretty nice guy, knows not to cross Granny Weatherwax.)
 * In Reaper Man, Death refers to playing a game called "Exclusive Possession", which he won, even though his opponent had got three streets and all the utilities.

"Death:"
 * In the third Discworld adventure game, Discworld Noir, Death remembers once being challenged to a game of "flog" (Golf). The soul he's collecting asks what kind of game it is.

""Some of them get to be very good at it, yes. I'm only an amateur, I'm afraid.""
 * In The Light Fantastic, Twoflower attempts to teach Death (and the rest of the Four Horsemen) how to play Bridge. It doesn't come easy:


 * But it will probably keep them occupied until the last trump...
 * I don't know if the challenge from Sourcery actually counts as a game, but it falls into the general category.
 * In American Gods by Neil Gaiman, Shadow plays checkers with the god Czernobog, who must join Shadow and Mr. Wednesday on their quest if Shadow wins, but will bash Shadow's brains out with a sledgehammer if Shadow loses. When Shadow does lose, he asks for one more game, same terms. Czernobog responds, "How can it be same terms? You want I should kill you twice?" Shadow points out that the Exact Words is that Czernobog gets one swing; as he is an old man, he might well miss, so the second game will be for a second swing. Shadow wins, and Czernobog agrees to the terms: he will help them, and then he gets one swing. At the end, Czernobog takes his swing - but just taps Shadow's forehead with the hammer. In Slavic mythology, Czernobog was half of a duology, the other half being his good twin Baeldebog whom Czernobog is now becoming. However, he says that he will not completely become Baeldebog until the next day, and chose to give Shadow just an honorary tap out of respect for him and his actions.
 * In the medieval poem The Devil and the Juggler, a juggler's soul is accidentally picked up and dragged to hell when he dies. (He was a rather pathetic fellow who didn't deserve it, but the demon was in a hurry.) The Devil asks him to stay and work in Hell, and he agrees. When the Devil leaves on business, a wanderer turns up and asks to be able to warm himself at the fire. The wanderer wants the juggler to play a dice game. When the juggler says he has no money, the wanderer suggests he "borrows" a few souls off his boss; he can always pay them back later. The wanderer turns out to be really lucky with his dice and basically wins all the lost souls of Hell, which he sets free. When the Devil comes home he kicks out the juggler's soul... who tries to enter Heaven. There he meets St Peter, Heaven's Doorman - who turns out to be the wanderer who was lucky at dice, and he happily lets the juggler enter.
 * Harry Potter and The Deathly Hallows and "The Tales of Beadle the Bard"- "The Tale of the Three Brothers". In which case each brother "tricks" death by crossing the river safely, and each wins a "prize". They unknowingly are putting up their lives for bargain, as the first brother (who wins an unbeatable wand), shouts about his good fortune so that another man slits his throat and steals it form him. The second brother has won a stone to reawaken the dead, and recalls back a past flame; but as the dead cannot belong among the living, his lover suffered back on Earth, and the second brother took his own life to be with her in the afterlife. The third brother had won a cloak of invisibility, which he used to "hide" from death until he was old and ready to "welcome Death as an old friend".
 * In Richard Adams' Watership Down, the story of "El-Ahrairah and the Black Rabbit of Inle" invokes this trope as the rabbit hero attempts to maneuver the Black Rabbit into accepting his life in exchange for those of the rabbits in his warren - once in a game of skill / chance, and then in a storytelling competition. El-Ahrairah loses both times.

Live Action TV

 * Scrubs once featured J.D. playing Connect Four with Death in an Imagine Spot, and Death wins on the diagonal, prompting J.D. to say "Very sneaky, Death!"
 * In The Twilight Zone episode "One For the Angels" a salesman talks death into letting him stay alive until he can make the sales pitch of a lifetime, e.g. "one for the angels." Death agrees, whereupon the salesman smugly quits his job. Unfortunately, Death still has to take a soul, and chooses a little girl who lives in the same building. To save her life, the former salesman distracts Death with a series of enthralling sales pitches, keeping Death occupied until after the appointed time - and willingly sacrificing his life in the process, since now that he's made his sales pitch of a lifetime, his bargain with Death is now complete.
 * In another episode from The Twilight Zone (the new episodes from the 1980s), "I Of Newton", Sherman Hemsley is a mathematician trying to solve a complex problem. In frustration, he says he'd trade his soul for the answer. And sure enough, the devil (played by Ron Glass) appears. The devil (wearing a red T-shirt with an ever-changing series of slogans, the most memorable being "Hell is a City Much Like Newark") says the only way Hemsley can save himself is to come up with a request the devil can't perform - i.e. a riddle he can't solve, a game he can't win, an object he can't retrieve, and so on. The devil describes in fantastic detail how he can instantaneously appear anywhere, any time; how he can zip into and out of parallel universes, imaginary dimensions, impossible situations. At last the devil says, "What is your request?" And Hemsley's reply? "Get lost."
 * And then there's another where the devil shows up to a few friends' Poker game, intending to take one of their souls. When the soul he picks challenges him to a card game to decide it, the devil slyly accepts, and promptly gets caught cheating. To save face, he decided to fill their fridge with beer instead of killing them all, proving that even the devil could be a good sport.
 * There's a Star Trek: Deep Space Nine episode where Quark thinks he's having to play a bizarre game with some aliens with the lives of his friends at stake, but
 * In Reaper, Sam plays quarters (a game bouncing coins into a shot glass) with the Devil. He loses. He plays again and is going to win...but an angel CRUSHES HIS HAND. Cause the forces of good don't want him to win. While it's all part of their plan, they really didn't need to be such assholes about it.
 * Parodied in Bottom when Eddie—as part of a ploy to trick Richie into letting him back into the flat after being kicked out—plays on Richie's recent fortune-teller inspired paranoia about dying by dressing up as Death. Richie challenges him to the standard game of chess, which hits a snag when 'Death' admits he doesn't know the rules. Richie then suggests Cluedo, which hits a snag when 'Death' reveals that he knows perfectly well that Richie always cheats by looking at the mystery cards. They settle on I-Spy, which hits yet another snag when 'Death' betrays an inability to spell.
 * In Six Feet Under, Nate has accidentally taken ecstasy, and dreams of playing Chinese Checkers with his dad, Death and Life. Death And Life (a white man in suit and a large black woman respectively) start having sex, and Nate's dad quotes the Bhagavad Gita.
 * In Sir Arthur Conan Doyles the Lost World, a female Death offers Roxton several chances to win back his life. Roxton accepts that he died and actually requests that she just claim him, but she says that if he doesn't try, his friend's lives will be forfeit, too. Death uses an hourglass to give the games a time limit, and Roxton fails at each one: Retrieve a diamond from a maze made of walls of fire (ran out of time), Retrieve a raptor egg (he tripped and dropped it), Guess which bowl holds oysters (guessed wrong). Each time he loses, Death captures another one of his friends. The final game is: shoot his own girlfriend, or himself. Roxton shoots the hourglass, making it impossible for the game to end. Death concedes victory to Roxton, and lets them all go.
 * In Supernatural Dean has one of these with Death: in exchange for bringing Sam's soul back to his body Dean has to do his job for a day. Dean ends up failing the test, but Death returns the soul anyway. Firstly because his real reason for the task was to show Dean what forces he was messing with by constantly resurrecting, and also because Sam and Dean's current investigation suited his purposes. He may have wanted a day off too.
 * A Halloween-themed episode of Benson involved Benson challenging Death to a game of Trivial Pursuit, wagering his life against that of the school bus full of children Death actually came to collect. Every question Death got had an answer pertaining to Death -- Jerry Garcia's musical group The Grateful Dead, Ronald Reagan's Western TV show Death Valley Days, etc. -- but Benson won because Death just hadn't been keeping up with popular film ... "Charles Bronson?!" (Death Wish)

Music
"'This morning I played chess with Death said the knight We played that he might grant me time My bishop and my knight will shatter his flanks And still I might feel God's heart in mine'"
 * The Charles Daniels band's "The Devil Went Down to Georgia" describes a fiddle-playing contest between Johnny and Satan.
 * Wigu parodied this. Satan challenges Topato Potato to a fiddling contest for custody of Sheriff Pony's soul. Topato wins by pointing out that Satan failed to explicitly define "fiddle" and the terms of victory, then proceeding to play the fiddle of the Butter Dimension Cubed, a tuba-like instrument whose only measure for proficiency is that one play it loudly.
 * And in Mono Puff's "The Devil Went Down to Newport", Satan and God go "surfing for souls". God wins, because Satan's hooves make it difficult to stand on a surfboard.
 * Tenacious D's song "Tribute" describes the band's encounter with "a shiny demon" who demands that they play "the best song in the world" or lose their souls. They do so and blow the stunned devil out of the water, but afterwords inform the audience that they can't remember how that song went, and "this is just a tribute".
 * The events that Tribute chronicles are seemingly the same as the song Beelzeboss in Tenacious D in The Pick of Destiny. Seems the D was embellishing a bit considering how their survival was mostly luck and had nothing to do with their song.
 * Don't forget the stoner parody entry into this, "The Devil Went to Jamaica".
 * Johnny Cash joined Charlie Daniels for "The Devil Came Back To Georgia", one of the few "sequel" songs in existence, as well as possibly the only one that features a Training Montage in the music, not the lyrics. (Johnny—from the song, not Mr. Cash—hadn't had time to practice much since his wife gave birth to their child...)
 * Sting gets in on the act. "The Soul Cages", from the same-named album, has a child get in a drinking contest against a hellish creature intent on keeping his father's soul. The enemy is 'the king of the ninth world/ the twisted son of the fog bell's toll', for clarification.
 * Scott Walker wrote a song about Bergman's The Seventh Seal (appropriately called "The Seventh Seal") which mentions the trope-naming chess game.

Mythology

 * Played with in the story of Sisyphus. The game was not a formal institution, but nevertheless he played it. Among his more popular exploits, he once evaded his fate by tying Charon to a tree and running off.
 * Greek Mythology: Arachne entered a weaving contest with Athena; in the end, Athena turned her into a spider. There seem to be a few variations on the tale.
 * Arachne won the contest. However, Greek Gods are just sore losers.
 * Arachne won and Athena drove her to suicide in revenge, eventually immortalizing her as a spider in apology for overreacting.
 * Both tapestries were exactly as beautiful as the other, but Arachne wove in mocking depictions of the Gods which is just Tempting Fate given her opponent.
 * Also from Greek Mythology, Marsyas entered a musical contest with Apollo. He lost, so Apollo flayed him. Why did Apollo flay him? Some would say it was because Apollo was that vain. Others would note that Marsyas, a satyr (aka horrendously ugly), stipulated that if he won, Apollo would have to do him some favors. This not to mention Marsyas's choice of performance, which ended up being a very bawdy flute piece against Apollo's divine cithara-plucking. Excessive punishment, yes, but not entirely undeserved.
 * At least one version has Apollo losing the first round, then demanding a rematch under his terms: that the musician must play while holding his instrument upside-down and singing. Since Marsyas was using a wind instrument, he had no chance.
 * From the ancient Egyptian tales of Prince Khaemwase, the sorcerer-prince Khaemwase Setna went on a quest to find the Book of Thoth. He found it, but it was guarded by an even better sorcerer, who challenged him to several games of draughts (checkers). Setna had no chance against a guy who'd been perfecting his game for several hundred years, and each time Setna lost, he would sink lower into the ground, and was due to be completely swallowed up on his fourth game. However, his brother managed to get the amulet of Ptah and save him before he was killed, allowing Setna to grab the Book of Thoth and run. Though Egyptian, this story is only known from the 1st century C.E.

Newspaper Comics

 * Dogbert once escaped death by walking away from the game (Scrabble in this case) on his turn and leaving the issue unresolved. Death should've specified a time limit beforehand.

Theater

 * The Seventh Seal's "challenge Death for more time" trope is cleverly spoofed in Woody Allen's short play "Death Knocks", where the protagonist plays gin rummy with The Grim Reaper for the right to stay alive one more day and a tenth of a cent a point "to make it interesting".
 * In Igor Stravinsky's opera The Rake's Progress, Tom plays cards with Nick Shadow for his soul. The odds are horribly stacked against Tom, because he has to correctly guess three randomly-drawn cards from an entire deck—but he wins thanks the The Power of Love. (Except Nick vengefully inflicts Tom with insanity as he leaves.)

Video Games

 * Dantes Inferno begins with the eponymous character getting murdered and the Reaper coming to take his soul. The game's first battle cum tutorial is the fight between Dante and the Reaper, which ends with Dante crushing the Reaper and taking his scythe.
 * In The Sims 2, if a Sim dies one of their loved ones can bargin for the dead Sims soul in some cases. If Death accepts, he plays a game of "Which hand is their soul in?" with the living Sim, success or failure is based on the relationship points between the two Sims.
 * In the original game, you played a game of Rock-Paper-Scissors with him. In the event of a tie, the dead Sim was brought partially back to life, as a Zombie.
 * The PlayStation 2 version has a fiddling contest. Never mind that that's Ol' Scratch.
 * The final stage of Guitar Hero 3 is a guitar battle against the Devil for your soul, to a heavy-metal remix of The Devil Went Down to Georgia.
 * Charlie Daniels has railed against this version, because of the possibility -make that probability- that the player loses (and thus the Devil wins).
 * The eponymous character in the old Genesis game Chakan gained immortality by beating Death in a duel. The point of the game is to get him to lose it. Death even shows up as a Bonus Boss.
 * In Touhou, defeating a Shinigami who comes for a human's life in a duel will extend their lifespan. However, it's usually Celestials and Hermits, ascended humans, who are able to consistently defeat the Shinigamis.
 * Tenshi's lucky in that the only shinigami to ever defeat her was only the ferrywoman of the Sanzu river - and was only after her because she was killing spirits.
 * In The Witcher, the ghost of a gambler challenges Geralt to a popular dice game for the soul of a boy Geralt has become guardian of. When challenged to mortal combat by a more powerful spirit of death for a soul, Geralt remarks, "Thank god; I was afraid you wanted to play chess."
 * Although Geralt can just beat the gambling ghost to true death using his sword if the player chooses. Which is what he does anyway if he loses at dice.
 * This is the whole point of Reaper's game in The World Ends With You.
 * The main villain of the Banjo-Kazooie series, Gruntilda Winkybunion, sets up the penultimate confrontation with the character as a GAME SHOW in the first two games. Not only that, but in the second game she gives quiz questions during the ACTUAL final battle; answering them makes her go easier on you because she's... just that nice?
 * More likely obsessive compulsive, given her reliance on speaking in rhymes in the first game
 * In Dragon Fable, Ash Dragonblade will,in his storyline,challenge Death to Tic-Tac-Toe

Web Comics
"Vlad: "It was meant to be a card game. Zebidiah believed because I had a head injury, I couldn't think. Well... And that of course was very true. But cheating always works well... So when I had the chance, I pulled out a gun and shot Zebidiah down.""
 * Irregular Webcomic had an early running gag where the various Deaths would admit that they had to accept any game as a challenge, whereupon the recently-departed would find some game their Death had never even heard of. Challenges have included poker, Quidditch, pod-racing, and Myth-busting, which ended up being the origin of Hitler's brain in a jar. "Pirate Slang" was deemed too humiliating by the Deaths, who let the pirates return to life.
 * It is also stated that chess is no longer an option, since in the 1970s, no Russians had died for about a decade. Apparently an earlier strip where chess was used was forgotten.
 * Given the huge amounts of time-travel in the comic, this may refer to another earth.
 * The Deaths do seem to be a bit trigger-happy with this, accepting the idea that Quidditch was just a coin toss.
 * And after Death of Insanely Overpowered Fireballs got Jar Jar and informed him of this option, Jar Jar picked pod racing. At which point Grim Reaper, being familiar with concept of Overpowered Fireballs, immediately decided that he is not suicidally insane.
 * In a tribute to Gary Gygax, xkcd has Gary playing D&D with Death. He's going to be there a while.
 * Aaron Williams neatly reverses the whole thing in this Backwards Compatible strip about the death of Dave Arneson
 * In this page of The Non-Adventures of Wonderella, Wonderella challenges Satan to a drinking match for her soul after using Satanic powers one too many times. She wins and not only does she get to keep her soul, but takes Satan's place.
 * A mild subversion occurred in the webcomic Those Destined : The other being was not death, and had no power to resurrect the protagonist. However, since he had bet his own soul, his nemesis was more than happy to help.
 * Let's not forget Problem Sleuth, where dead characters are almost always sentenced to a battle with Death in any boardgame other than chess. Such as the Game of Life. Death loves Life.
 * Although some find it easier to simply walk out of the afterlife's door instead of playing.
 * Three Panel Soul inverted the trope - the mortal narrator won the Devil's eternal soul in a game of mancala. He eventually traded it to an angel for "the ideal method of grilling grilled corn on the cob."
 * Kukuburi. The female protagonist plays battleship with a well-dressed, while tacky, skeleton Card-Carrying Villain who suggests to be Death (and later refutes her "misconception"). The ships take the form of the flying whales present in the environment. She does not know that the attacks are reflected as bombs thrown against real flying whales - including the whale where her friends are travelling in an attempt to rescue her. Besides, he cheats.
 * In Order of the Stick, it all depends on choosing the right contest.
 * In Mortifer, Vlad tells the story of how, after receiving a grievous head injury from hitting a demon with his car, he challenged said demon to a game, in order to keep the demon from killing him.


 * Not only did it work, it left Zebby unconscious long enough for Vlad to tattoo his name on Zebidiah's arm, enslaving him.

Western Animation
"Hark: Open...the window...let the birds... sing. Death: What?! What did you say? Hark: (stronger) Open the window, let the birds sing. Death: Nooo!!! (disappears into the shadows)"
 * In " Death Meatballs or Consequences", an Animaniacs pastiche of Seventh Seal, they play checkers (as Dot and Yakko say that chess is unknown to them) for Wakko's life with Death. They play to stay together, which Death interprets as taking all three, but Death finds them too annoying to keep dead.
 * The entire reason The Grim Adventures of Billy and Mandy exists. Billy & Mandy played a game of limbo with Grim for the soul of their dead hamster. Grim lost thanks to Mandy's cheating and now he is stuck being their best friend slave forever. Cue the rest of the series with hilarious results.
 * Additionally, an old lady has beaten Grim at just about everything, thus revealing to Mandy that this woman has beaten death itself.
 * In the Futurama episode "Hell Is Other Robots", the Robot Devil explains that the Fairness In Hell Act requires him to give visitors the option of challenging him to a fiddle contest to win back a robot's soul (in this case, Bender's). A solid gold fiddle is even part of the deal. Losers only get a smaller, silver fiddle, and the Robot Devil may kill them at his discretion (in this case, Fry). Of course, playing well on a solid gold fiddle is pretty hard as it is, and the Robot Devil's prehensile tail serves as a third arm. Leela, who accepted the challenge with the explanation that playing the fiddle was just like the drums, yells "Time for the drum solo!" and beats the Robot Devil unconscious with the gold fiddle.
 * Darkwing Duck dies in a motorcycle accident because he refused to wear his helmet in the heat of pursuit. Eventually he challenges the Grim Reaper for one more hour in the world of the living so he can defeat the criminal he was chasing. The game? Darkwing does a cute finger trick with his hands. Death, lacking necessary muscles, tendons and other body parts, fails to copy him.
 * In the animated short Come Again in Spring, the elderly Hark is approached by Death himself during the middle of the winter, claiming that it is his time to die. Hark, however, has other ideas—as the birds he feeds every day normally migrate during the winter they will die without his support, so he tells Death to come again in spring. In this example however, it is Death who ultimately makes the challenge, and boy is it a doozy: he gives Hark one day to remember the type of cake that his mother served him on his second birthday. When Hark finally remembers, death is furious and decides to prolong the game by asking him to remember what wildflowers his mother picked for him on his first birthday. Hark gets it right again (buttercups if anyone was interested), and Death, fed up, offers a third, final question: on the day that Hark was born, what were the first words his father said to him as he held him for the first time? Understandably this has Hark stumped, and he begins to wither away as the deadline draws near. When Death finally arrives to claim him, however...


 * A Nightmare Sequence in Nightmare Ned featured Ned playing checkers against the Tooth Fairy in order to keep his teeth.
 * Regular Show had Skips arm wrestling with Death with his soul on the line to bring back Rigby, whom he had killed in the first place. Skips cheated by using an arm brace, but got away with it.
 * On Adventure Time we have Finn getting in a music battle against Death to save the soul of a plant.