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. "Remind me again," he said, "how the little horse-shaped ones move."
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 BC - 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 was 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 was a rarity.
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?. See also The Problem with Fighting Death.
Not to be confused with Human Chess where the pieces are humans and captured pieces are sometimes killed.
As a Death Trope, all Spoilers will be unmarked ahead. Beware.
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 his larger Thanatos Gambit.
In Top 10 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. Just to clarify, being color blind means that you can't distinguish between two colors, usually red and green. It does not mean that you can't see "in color." Thus, black-white color blindness means you can't tell if somethings black or white. You can see other colors just fine. You can also see the black and white objects just fine, you just can't tell if they are black or white.
The Brazilian comic book Turma da Mônica Jovem (Teenage Monica's Gang) plays with this trope on edition 40. Cebolinha (Jimmy Five) brags about being an online chess master, but fails miserably to win a single match when playing on a real chessboard. He buys an old chessboard in a local store run by a strange sexy girl. She lets him take it for free, as long as he plays a match against her some day. He agrees and seeks to learns the rules of chess. He eventually becomes an expert player, and even wins a local chess contest. Later in the story, he meets the strange girl again, and she reveals to be no other than Death herself. She reminds Cebolinha of his earlier promise, and they start a match. The pieces come to life, portrayed by Bug-A-Boo, Bubbly and other in-universe characters - culminating with the Queen portrayed by Monica - Jimmy's (not so) secret passion. As he begins to fall short of pieces, he commands the King to come out of his castled position and attack. He partially succeeds until he finds himself at the verge of sacrificing the Queen in order to win the match. He refuses to do so, claiming that he loves her too much to endure her loss. The Queen retorts that she is not actually Monica, that it was him who brought her to life - and that the Queen's role is to protect the King, not the contrary. He ignores her and advances anyway. The Death, impressed by his love and determination, quits the match by dropping her King. She then greets Jimy for being so determined and pure-hearted, stating that many great leaders along human History (such as Napolean Bonaparte) were skilled chess players.
Famously occurs in Ingmar Bergman's The Seventh Seal, pictured above. This is the better known origin of the "chess with the reaper" form of this trope.note But not 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. The knight also tips over the chess board (mainly to distract Death so that Death won't see his friends slipping away) and claims not to remember where the pieces were. Death, however, has not forgotten.
In the 2011 short film Dave Vs. Death, David Kane dies, and in the void between life and the afterlife he propositions Death for a game of chess. The rules dictate that for every piece David loses, one of his loved ones will die. By the end it's revealed as a Xanatos Gambit on David's part: all his friends were plotting behind his back, so if he beat Death then he would regain life, but if he lost, then he would take all his false friends with him to the grave. Death doesn't like the fact that Dave cheated to win and starts a new game, although Dave's "friends" are still dead. Death is played by Julian Richings, who had earlier portrayed Death in Supernatural.
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.
Live Action TV
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.
Holly: Name me a game.
Holly: It can be anything at all.
Holly: Draughts, poker, any game at all.
Holly: Subbuteo, Snakes And Ladders, you name it.
Holly: Monopoly, maybe? I'll let you go first.
Holly: So you like a bit of chess then, do you?
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 a master at). By the time they try to pull out Barrel of Monkeys, Death's had enough.
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.
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.
The original promotional video for "Vérone" from Romeo et Juliette: De La Haine a l'Amour included Prince Escalus playing chess with a mysterious and unidentified old man while the events of the story the musical is based on play out around them in a highly compressed format. Given that promo videos for French musicals are often designed and filmed long before the show itself opens or is even being properly rehearsed, and since Death is a character in the show (albeit in the form of an Amazonian Beauty dancer), it's probable that this trope was being invoked before the Death character concept was finalized.
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.
Duel Master 1: Challenge of the Magi (one of a series of game books, a la Fighting Fantasy, designed for two players) 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.
In Talisman, playing chess is one of the random events that happen when a player character encounters the Grim Reaper NPC. In terms of game mechanics, this simply results in the player in question missing their next turn.
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.
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?
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).
Examples With Non-Chess Games
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.
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 end the world.
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.
In the My Little Pony: Friendship Is Magic fanfic Near Death Experience, the protagonist Pinwheel and two other ponies meet Death, who will let them go if they can best him in challenges of strength, skill and wits. Death wins the first two challenges easily and claims the other two ponies, but lets Pinwheel go when she wins the Test of Wits.
The Seventh Seal example is parodied in Bill & Ted's Bogus Journey, with the heroes besting the Reaper (who, in this movie, looks almost exactly like he did in The Seventh Seal) instead in games like Battleship, Clue, and Twister. The Reaper is a Sore Loser here, insisting a rematch each time he loses. Eventually the Reaper gives up and joins them. 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. Likewise, in the novelization, the villain tries to invoke this after he is killed, coincidentally suggesting the same games Bill and Ted played with Death. The Grim Reaper refuses since he just found out he is really bad at those games.
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 "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!
In Coraline, the cat suggested this to the titular character since the Other Mother loves to play games. So Coraline challenged the Other Mother to a game where she would find her parents and the three lost children's souls. If she loses, she would stay with the Other Mother forever.
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 four ones" (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.
I was the boot.
In 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.
Death:An extremely stupid one to play against someone who spends every second practicing his swing.
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:
Did you say humans play this for fun?
"Some of them get to be very good at it, yes. I'm only an amateur, I'm afraid."
But they only live eighty or ninety years!
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 Beedle 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 from 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, a god of death, into accepting his life in exchange for those of the rabbits in his warren - once in a game of bob-stones (the lapine equivalent of liar's dice) and then in a storytelling competition. El-Ahrairah loses both times.
Live Action TV
A Halloween-themed episode of Benson involved Benson challenging Death to a game of Trivial Pursuit, wagering his life against that of a school bus full of children in an accident whom Death actually came to collect. While it at first seams like Death is cheating (the answers to the first questions Benson asks are Death Valley and the Dead Sea, respectively), Benson wins because Death just hasn't been keeping up with popular film. (The answer to the third question, which he misses, is Death Wish.) Benson struggles with his third question too ("What was the name of the pet pig on Green Acres?) but remembers at the last second the answer: Arnold.
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 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.
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 "Pretty sneaky, Death!"
In Sir Arthur Conan Doyle's 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 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.
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 it turns out that it's just a game and characters dying in-game are fine in the real world once the game ends.
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.
In the 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.
The Twilight Zone episode "A Game Of Pool" features this when a man (Jesse Cardiff) who dedicated his life to pool would "give anything" for a chance to play Fats Brown, the pool player that everyone says was the best, and better than Jesse is. Fats Brown then gets a call from his heavenly pool table to report to Jesse's pool hall, where Fats then appears and accepts Jesse's challenge - if they stakes are for Jesse's life. Jesse accepts, and they play pool. Both are very good, but Fats gets on Jesse's nerves when he notes that all Jesse did was pool - he didn't get married or see the world or anything. Jesse thinks that Fats is just trying to psych him out. Before making the final shot, Fats says that winning this game may have undesired consequences - but Jesse blows him off. (Fats adds that he was required to say that.) Jesse makes the shot, and Fats acknowledges that Jesse is, in fact, the best pool player ever. Jesse laughs hysterically for a while - but the scene then cuts to Jesse asleep at the heavenly pool table, getting an announcement to report to a pool hall in Sandusky, Ohio. In the meantime, Fats Brown has gone fishing.
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.
In "Doctor Who" the First Doctor and his companions have to play games against the Celestial Toymaker, who appeared again a few times in the Expanded Universe.
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.
'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'
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 Fategiven heropponent.
Arachne LOST fair and square, and hung herself. Out of pity, Athena changed her into a spider so that she and her descendants could have all of eternity to practice their weaving.
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.
There is an old Bavarian folk tale about how Bavarian Death (Boandlkramer meaning something like Bone huckster) is supposed to collect an old man who died from being shot while poaching. He makes Death drunk and plays cards with him, cheating in the course of the game and winning ten more years on earth. However, Death has to keep book, so he takes the poacher's granddaughter 10 years early for the statistics to work out. When she arrives in Bavarian heaven (really!) the mistake comes to light and Death has to persuade the poacher to forfeit his additional 10 years for his granddaughter's sake.
Dilbert: 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.
One route players can take through the inner region in Talisman forces the player to "Dice with Death" by rolling dice against the Grim Reaper. If the player rolls higher, the player's character can progress further towards the Crown of Command. If the Grim Reaper rolls higher, the character loses a life and must dice with death again on subsequent turns until the player either wins or the character is killed.
Exalted: there is the demon Sigereth, The Player of Gamesnote part of Madelrada, That Which Wears Down The Mountains; who herself is part of the Yozi known as Kimberry, The Sea That Marched Against The Flame. You can issue a challenge to him, either via sorcery or by floating a letter of challenge down a body of water when you're an undefeated champion of a game. If you lose, you're turned into a soulless mannequin. If you win, you can demand something that the Demon City has, including restoring someone who lost to him. Challenging Death itself is not possible though, due to the No-Resurrection meta-rule.
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.)
Dante's 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 bargain 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.
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.
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 Pirate101 Captain Blood manages to obtain immortality when he challenges Death to a game of poker. However it's not because he beat Death. He's immortal because after Death showed a winning hand he left the table for a bathroom break. Since he has never played his hand, Death still hasn't technically won so Death can't claim his soul. Death is ticked about this and has rewritten the rules to ensure this doesn't happen again.
In the PC game Wishbone and the Amazing Odyssey, dying causes Wishbone to play an unnamed board game with Pluto (Hades). The first to the potion of Asclepius that restores life wins. Opting out of playing is an automatic game over.
In Socrates Jones Pro Philosopher, Socrates and his daughter Ari are sent to the philosophers' afterlife realm after getting into a car accident. Ari convinces the Arbiter there to let Socrates return back to the living world (she's actually still 'alive', but Socrates is not) if he can give an acceptable answer to a centuries-old "wager" of what the true source of morality is — a wager that incidentally has been answered correctly only once in all of human history. Oh, and if he fails, both of them will become trapped forever in the afterlife.
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 - though with 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.
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
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 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.
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."
Not only did it work, it left Zebby unconscious long enough for Vlad to tattoo his name on Zebidiah's arm, enslaving him.
In thisSkin Horse, Tigerlily Jones explains how she won the plans for her ultimate weapon by beating the devil at Jenga.
In The Gamers Alliane, the rebel leader Mae Torazo ends up playing chess with the Grim Reaper after her death. She wins the game and is allowed to possess her corpse for a limited period of time to have her revenge on the people who murdered her.
In Survival of the Fittest V5, Tessa Blackridge, given her choice of game (except Twister) to challenge Death for her life, chooses Go Fish. She loses.
A young boy is seen competing against death in some unseen mobile/handheld video game in this T-Shirt, apparently successfully given that it is entitled "...And Billy Lived Forever"
In "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. (The Warners win, but they blatantly cheat, and for some reason, Death fails to notice.) 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 & 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 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 dealnote Fry asks about its practicality, thinking it'd weigh hundreds of pounds and sound terrible; the Robot Devil says it's more for show than anything else. 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.
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...