%% Image selected per Image Pickin' thread: http://tvtropes.org/pmwiki/posts.php?discussion=1334407181008200100
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[[quoteright:350:[[Film/TheSeventhSeal http://static.tvtropes.org/pmwiki/pub/images/rsz_seventh_seal_chess_5978.png]]]]

->''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. "[[foldercontrol]]

[[folder: Remind me again, ]]
" he said, "[[/folder]]

[[folder: how the little horse-shaped ones move. ]]
-->-- ''Discworld/SmallGods''

A character gets into a contest of some sort with TheGrimReaper, {{Satan}}, or some other supernatural entity, usually with some dire consequence if the human loses.

This is OlderThanFeudalism, 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 is 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 TheGrimReaper to a TabletopGame/{{chess}} game in return for a longer life, hence the trope title. See also EnemiesWithDeath and SmartPeoplePlayChess. But it doesn't have to be chess--if the player is allowed to ''pick'' the game, [[CookingDuel absolutely anything can happen]].

Compare DidYouJustScamCthulhu for when you cheat death in this game (which may be the origin of the idiomatic phrase). See also TheProblemWithFightingDeath.

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

'''As a DeathTrope, all Spoilers will be unmarked ahead. Beware.'''

!!Examples with Chess

* The UrExample of this trope can be found in Sweden, in the Täby Church near Stockholm. The church displays a fresco "Death playing chess", painted by Albertus Pictor. See [[https://www.europeana.eu/portal/en/record/2063602/SWE_280_001.html Death Playing Chess]]
[[folder:Comic Books]]
* Used in one issue of ''ComicBook/MarvelAdventures: Avengers''; the Avengers end up playing HumanChess with [[PlanetEater Galactus]] over the fate of an alien world. Hulk screws up and it's [[http://img222.imageshack.us/img222/8554/maavengers26017tt6.jpg a stalemate]], so they try [[http://i159.photobucket.com/albums/t142/robertroberts_2007/Capture-Copy-9.jpg in a human-scaled stadium baseball.]] Ant-Man [[http://img222.imageshack.us/img222/630/maavengers26019zk6.jpg screws it up]], so they play [[http://img222.imageshack.us/img222/6718/maavengers26020is5.jpg poker]]. Hulk screws up again, and then SpiderMan mentions that he's hungry and they end up in an [[http://img222.imageshack.us/img222/4813/maavengers26021se2.jpg infinite-star restaurant.]]
* The Creator/MarvelComics 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 [[BalancingDeathsbooks had to die in his place]]. This turned out, however, to be part of his larger ThanatosGambit.
* In ComicBook/TopTen spin-off ''ComicBook/{{Smax}}'', there is actually a specific Death responsible for playing chess with "wily peasants". His name is Lionel. Naturally, he even looks like the GrimReaper in ''Film/TheSeventhSeal''. Just as naturally, he isn't very good at chess (that's why the peasants always win).
* In Grant Morrison's ''ComicBook/{{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 something's 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.
* One comic in [[Webcomic/{{Exiern}} Exiern]] featuring a female death has an old man challenge her to a game of chess for his life. She strips naked, and [[DistractedByTheSexy he can't concentrate on the game]] enough to win.

* Famously occurs in Ingmar Bergman's ''Film/TheSeventhSeal'', 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 [[http://upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Taby_kyrka_Death_playing_chess.jpg/450px-Taby_kyrka_Death_playing_chess.jpg 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)[[/note]] 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.
** This scene was lampooned in ''[[Film/FiveHundredDaysOfSummer (500) Days of Summer]]'', with Cupid replacing Death.
* Parodied hilariously in ''[[Film/BillAndTed Bill & Ted's Bogus Journey]]''. The boys challenge Death, but [[BookDumb since they don't know the rules of Chess]], they convince him to play other games... like {{TabletopGame/Clue}}, {{TabletopGame/Battleship}}, and Twister. Because Death is a SoreLoser, he keeps challenging them to "best two out of three", "best three out of five", and so forth until he finally gives up. In the original script (used for the novelization and comic adaptation), this becomes a ChekhovsGun during the final showdown, wherein where Bill and Ted get killed several times by their evil robot duplicates and get Death to bring them back by bringing up all the times they beat him.
* Short film ''Film/TheDove'', another Bergman parody, has the heroine playing ''badminton'' with Death.
* In the 2011 short film ''Dave Vs. Death'', David [[NameOfCain 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. [[spoiler:By the end it's revealed as a XanatosGambit 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 Creator/JulianRichings, who had earlier portrayed Death in ''Series/{{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 DealWithTheDevil. 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 Creator/TeresaEdgerton's ''Literature/TheGrailAndTheRing'', Tryffin plays a series of chess matches with the king of TheFairFolk 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 ''Literature/{{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 ''Literature/TheDemonata'' 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 [[BigBad 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.

[[folder:Live-Action TV]]
* The opening to ''Series/TheColbertReport'''s "Cheating Death" segment shows Stephen Colbert tricking Death into looking away, then rearranging the pieces, as well as several other forms of cheating such as playing a ShellGame. In the final episode, [[spoiler:Death finally catches Stephen cheating and tries to kill him, so Stephen shoots and kills Death in self-defense, thus making himself immortal.]]
* Parodied in ''Series/BigWolfOnCampus'', 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 ''Series/{{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.
* ''Series/TheYoungOnes'': The episode "Nasty" starts with a direct homage to ''Film/TheSeventhSeal'', where Death loses. Then kills his opponent anyway.
-->'''Death:''' Checkmate? Bollocks to this!
* ''Series/BuffyTheVampireSlayer'' lampshades this trope.
-->'''Xander''': If Death ever tries to challenge you to a game of Chess, don't. He's some kind of whiz.
* The concept is parodied in ''Series/{{Beetleborgs}}'', where the Grim Reaper is Little Ghoul's uncle, and plays chess with his niece simply to pass the time.

* Music/Starflyer59's [[http://www.youtube.com/watch?v=SDuQhga4iSk "No New Kinda Story"]] music video is a very clear ShoutOut to Bergman's chess match. (Although the hooded figure could be interpreted as {{God}} instead of Death; the video is something of a MindScrew.)
* 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 ''Theater/RomeoEtJulietteDeLaHaineALamour'' 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 AmazonianBeauty dancer), it's probable that this trope was being invoked before the Death character concept was finalized.

[[folder:Tabletop Games]]
* One of the 50 game scenarios, called Haunts, in ''TabletopGame/BetrayalAtHouseOnTheHill'', 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. This is expected and usually required, as Death himself also cheats by rerolling all blank dice after his first roll and has a massive Knowledge stat that is otherwise near-impossible to overcome without the players cheating.
* ''Duel Master 1: Challenge of the Magi'' (one of a series of game books, a la Literature/FightingFantasy, 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 ''TabletopGame/{{Talisman}}'', playing chess is one of the random events that happen when a player character encounters the GrimReaper NPC. In terms of game mechanics, this simply results in the player in question missing their next turn.

[[folder:Video Games]]
* The player in ''VideoGame/AFineDayForReaping'' 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 InteractiveFiction, and your character isn't very good at it. You have to read an encyclopedia to beat the person at chess, in fact.
* Not literal chess, but in ''VideoGame/KingsQuestVIHeirTodayGoneTomorrow'', Alexander gets to challenge Death to save the souls of his lover's parents AND to leave the Realm of the Dead free. The challenge is especially difficult: make Death cry. Alexander succeeds.
* The premise of ''VisualNovel/UminekoWhenTheyCry'' 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 HumanChess with his family as the chess set.
** [[DisSimile It's also nothing like chess]].
* In ''VideoGame/TheSims3'', 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 [[Videogame/WorldOfWarcraft Karazhan]]. Failure to win the game results in the players' deaths. Medivh cheats.
* In ''VideoGame/FallenLondon'' this is one of a number of ways for your character to return to life after being killed. You can also play dice.
* Lampshaded, like everything else, by Geralt in ''VideoGame/TheWitcher''. (When confronting [[spoiler:the King of the Wild Hunt]] at the end of the game.)
--> '''[[spoiler:King]]:''' ''"You want to fight me? So be it. Your flight from death ends here. Draw your sword!"''
--> '''Geralt:''' ''"I was afraid you'd suggest chess."''
* The ''VideoGame/CrusaderKingsII'' expansion "The Reaper's Due" added an event where an ageing character plays a game of Chess with a random courtier whom he realises is Death. Success grants bonus health (making that character live longer) whereas failure means Death collects.

* In ''Webcomic/CaseyAndAndy'', beating the devil at chess to undo selling his soul was part of [[TheAce Quantum Cop's]] GambitRoulette to defeat Quantum Crook in one StoryArc.
* Parodied in the webcomic ''[[http://www.webcomicsnation.com/captaineli/captianeli/series.php?view=archive&chapter=41097 Life and Death]]'', in which nothing is at stake but Death still wins every game. He does, however, have [[http://www.webcomicsnation.com/captaineli/captianeli/series.php?view=archive&chapter=41174 one weakness]].
* ''Webcomic/DeathAndTheMaiden'': 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 [[DeaderThanDead death]] with the chess board.
* Also parodied in ''Webcomic/LifeAndDeath'' (not to be confused with the above) as Steve (Death) has [[http://www.drunkduck.com/Life_and_Death/index.php?p=482044 anger management problems when he loses]]. And for goodness sake, [[http://www.drunkduck.com/Life_and_Death/index.php?p=485581 don't try it with pool]].
* [[http://www.dawnoftimecomics.com/index.php?id=291 This]] ''Webcomic/DawnOfTime'' strip features an unconventional gambit.
* ''Truck Bearing Kibble'' has [[http://web.archive.org/web/20120503000201/http://truckbearingkibble.com/comic/2008/11/03/blue-screen-of-death/ this]] variation.

[[folder:Web Original]]
* In Lawrence Friday's LetsPlay of ''VideoGame/DantesInferno'', Lawrence explains why Death is so easily beaten in a physical fight:
-->'''Lawrence Friday:''' Yeah, I'm guessing what it is, everybody goes for the chess game, and Death has just ''perfected'' his chess game. But when it comes to [[VideoGame/SuperSmashBros Final Destination]]...
* The Slimebeast creepypasta ''[[http://slimebeast.com/stories/chess_champion.php Chess Champion]]''. Relatively unusually for this trope, it is Death who issues the challenge, apparently purely for his own amusement. The champion makes Death regret it, though, by [[spoiler:deliberately getting into a stalemate with only the kings remaining.]]
-->'''Champion:''' "[[spoiler:I have nowhere important to be, but I'm guessing you have rather a lot of work piling up. I wanted to see you resign.]]"
* ''WebVideo/StarWarsUncut'': Obi-Wan Kenobi and Darth Vader play chess instead of having their lightsaber duel in a 15 second clip inspired by ''The Seventh Sign''.

[[folder:Western Animation]]
* The animated film ''WesternAnimation/{{Animalympics}}'' lampoons ''Film/TheSeventhSeal'''s iconic scene mentioned above with the film being called "Price and winnies" and directed by [[MeaningfulName the avian]] [[NoCelebritiesWereHarmed Ingmar Birdman]]. The role of the Death is played by the horse Bjorn Freeborg and we see the famous scene with him saying the following:
--->'''Bjorn Freeborg:''' "I remember, as a little boy by the seaside. It was a game, and I knew I had won."!
* ''WesternAnimation/EarthwormJim'':
--->'''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 ''Literature/{{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 TwoHeadedCoin) but it turns out to be AllJustADream (the episode where this happens is a parody of ''Film/TheWizardOfOz'').

!!Examples With Non-Chess Games

[[folder:Anime & 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 [[BrotherSisterIncest his sister]], so things get complicated. OneThingLedToAnother, 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 ''Anime/SummerWars'', [[spoiler:Natsuki takes advantage of the fact that [[AIIsACrapshoot Love Machine]] treats everything as a game and played several matchs of Koi-Koi with it. She managed to [[MundaneMadeAwesome 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 ''LightNovel/HaruhiSuzumiya'', notably the baseball and Day of Sagitarius episodes, if the [[TrueCompanions SOS Brigade]] lost either of these games, [[RealityWarper Haruhi]] would become infuriated and end the world.
* The entire premise of YuGiOh. In early volumes of the manga, Yugi challenges naughty people (mostly bullies and liars) into various "Shadow Games", and punishes them once they inevitably lose (he's the Yu-Gi-Oh! - the King of Games, after all), typically by trapping them in endless illusions with his mystical ancient power. Later in the series when the manga starts to be written in arcs and adopted in the anime (focusing almost exclusively on the Duel Monsters card game), Yugi has to face his matches that are equally capable of banishing his and his friends' souls into the Shadow Realm, such as Bakura and Marik.

[[folder:Comic Books]]
* In one issue of ''Comicbook/GhostRider'', Ghost Rider races against Death for the lives of a man, a little girl, and himself. The Rider cheated by kicking Death into a ravine.
* Jack from ''Comicbook/{{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 BagOfHolding 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.
* ''ComicBook/GrooTheWanderer'' once had a sword fight with Death. Groo won.
* Franchise/TheFlash has escaped Death by beating him in a race on numerous occasions. This is even a ''game mechanic'' in the GBA version of ''Justice League Heroes''!
* One man has the audacity to play Lawn Darts with Death. That man is ''ComicBook/FlamingCarrot''.
* ComicBook/{{Wolverine}} has at times engaged in battle with [[SignificantAnagram Lazaer]], the Angel of Death, for the right to return to his body.
* In the Creator/MarvelMAX ''Destroyer'' miniseries, the eponymous character is allowed to come back after winning a fistfight against several reapers.

[[folder:Fan Works]]
* In the ''Manga/DeathNote'' fic "FanFic/ACureForLove" L challenges Ryuk to a game of tag.
* In the ''Manga/DeathNote'' fic "Fanfic/KiraSweetheart" L gets Ryuk hooked on ''VideoGame/EverQuest''.
* In the ''WesternAnimation/MyLittlePonyFriendshipIsMagic'' fanfic ''[[http://www.fimfiction.net/story/9672/near-death-experience 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.
* In a weird way, the four are playing a kind of {{LARP}} for their lives against Jeft in ''Fanfic/WithStringsAttached'', though they don't know it. He throws them in with his favorite gaming character, Jim Hunter, in an effort to get them to fight, which is something Jeft has been itching for over the course of the book. However, the four “beat” Jeft by befriending Jim instead of fighting him. And Jeft indeed has several tantrums over this, especially when Jim decides to give up his {{BFS}} and return with the four to C'hou. The tantrums are meant to be quite lethal, but the first (the Battle on the Plains of Death) sees the four and Jim winning, and the second (when Jeft brings Blackfire to life and it tries to kill the four while Paul tries to separate it from Jim) is averted when the four decide to just leave rather than rescue Jim.
* In the ''WesternAnimation/MyLittlePonyFriendshipIsMagic'' fan comic [[http://wadusher0.deviantart.com/art/Time-Fades-Pinkie-Pie-1-608481403 Time Fades]], Pinkie makes a deal with Death. If she can make Death laugh, she gets one free mulligan.

* ''Film/TheSeventhSeal'' example is parodied in ''[[Film/BillAndTed 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 [[BestOutOfInfinity Battleship, Clue, and Twister]]. The Reaper is a SoreLoser here, insisting on a rematch each time he loses. Eventually the Reaper gives up [[DefeatEqualsFriendship 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 Twin}}s 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 ''Film/{{Crossroads 1986}}'' is a guitar battle between Eugene and [[Music/SteveVai Jack Butler]] (the Devil's chosen one) for Willie Brown's soul. Eugene wins.
* ''Film/PiratesOfTheCaribbeanDeadMansChest'': 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 wants is the key's location, so he can 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.
* Creator/FritzLang'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 [[BalancingDeathsBooks 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 ''WesternAnimation/{{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 has to find her parents and the three lost children's souls. If she wins, the Other Mother has to let her go. If she loses, she must stay with the Other Mother forever. [[spoiler:As it turns out, the Other Mother has no intention of letting Coraline go even if she wins the game, so Coraline has to trick her into letting her escape.]]
* In ''Film/TenaciousDInThePickOfDestiny'', the song "Beelzeboss" shows the aftermath of the devil managing to break the seal put on him by a wizard and coming to Earth, intending to end it. Tenacious D challenges him to a rock off: if they win, he must return to hell; if he wins, then Kage will be taken back to hell with Satan for [[BlackComedyRape conjugal purposes]]. In the end, Tenacious D is [[spoiler:outclassed in skill - at least according to the devil - but win due to luck and knowing the story of how he was beaten last time]].

* In Creator/SamuelTaylorColeridge's "Literature/TheRimeOfTheAncientMariner", Death and Life In Death gamble with dice, and Death wins the crew, while Life In Death wins the Mariner, and gives him a FateWorseThanDeath.
* In the ''Literature/{{Discworld}}'' series, Death is often challenged to these. Again, with the twist that he can't lose (unless he wants to). For example:
** In ''Discworld/{{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 [[BalancingDeathsBooks 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 [[/folder]]

[[folder: four ones ]]
" (Death, in addition to being [[DontFearTheReaper a pretty nice guy]], knows not to cross Granny Weatherwax.)
** In ''Discworld/ReaperMan'', Death refers to playing a game called "[[TabletopGame/{{Monopoly}} Exclusive Possession]]", which he won, even though his opponent had got three streets and all the utilities.

[[folder: I was the boot. ]]

** In ''VideoGame/DiscworldNoir'', Death remembers once being challenged to a game of "flog" (Golf). The soul he's collecting asks what kind of game it is.
--->'''Death:''' [[/folder]]

[[folder: An extremely stupid one to play against someone who spends every second practicing his swing. ]]

** In ''Discworld/TheLightFantastic'', Twoflower attempts to teach Death (and the rest of the Four Horsemen) how to play TabletopGame/{{Bridge}}. It doesn't come easy:

[[folder: Did you say humans play it for fun? ]]

--->"Some of them get very good at it, yes. I'm only an amateur, I'm afraid."

[[folder: But they only live eighty or ninety years! ]]

* In ''Literature/AmericanGods'' by Creator/NeilGaiman, Shadow plays checkers with the god [[Myth/SlavicMythology 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 ExactWords 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 [[EvilTwin good twin]] Bielebog whom Czernobog is now becoming. However, he says that he will not completely become Bielebog 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.
* ''Literature/HarryPotterAndTheDeathlyHallows'' and ''Literature/TheTalesOfBeedleTheBard''- "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' ''Literature/WatershipDown'', 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.
** The ending implies this is how El-Ahrairah ascends to become a TricksterGod. The utterly crushing defeats (both psychologically and physically; while the Black Rabbit is not evil, there are ''consequences'' for challenging him) in the very things he's legendary for and subsequent realization that all his cleverness and manipulative skills did nothing more than drive him and his charges straight to this point finally purges him of hubris and makes his intended sacrifice worthwhile.
* ''Literature/{{Pact}}'', the protagonist challenges [[HorsemenOfTheApocalypse Conquest]] to a contest in order to safeguard his freedom, specifically mentioning ''Film/TheSeventhSeal''. Conquest points out that the one challenged in the movie was ''Death'', not Conquest-but he accepts anyway when it's pointed out to him that this is a chance to crush someone under his heel while they're engaged in a futile act of defiance, which is within his nature as much as it is in Death's nature to struggle with all living things.
* The Warhammer novel Bane of Malekith uses a version of this trope as a framing device. Caledor Dragontamer, greatest mage of the elves of old, has trapped himself beyond space and time to hold open the world-saving magical vortex that was his last gift to his people. While trapped, he must play a game with Death (strongly hinted to be the elven war god Khaine) for the fate of the elves and the Warhammer World - though the pieces of the game are the mortal elves and immortal daemons battling it out in reality, and the game is in fact the unfolding events of history as they happen. Given that Warhammer is a tabletop wargame, the meta-fictional implications of this are all too apparent. It becomes clear throughout the book that Caledor and Death have played this game many times before, and thus far Caledor has always won, though never more than barely. The novel ends with Death offering a cheery "perhaps next time I shall win eh?", and an exhausted Caledor muttering "perhaps next time I will let you".
* The Bavarian story ''Der Brandner Kaspar'' by Franz von Kobell is about someone who tricks the ''Boandlkramer'' (Grim Reaper) into playing cards for some more years of life, then gets the reaper drunk and cheats so win more years. Eventually, he will go with the reaper because all of his loved ones die.
* ''Literature/TheStoryOfTheYouthWhoWentForthToLearnWhatFearWas'': The youngster spents three nights in a haunted castle, where he plays nine-pins with a bunch of skeletons.

[[folder:Live-Action TV]]
* A Halloween-themed episode of ''Series/{{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 ''Film/DeathWish''.) Benson struggles with his third question too ("What was the name of the pet pig on ''Series/GreenAcres''?) but remembers at the last second the answer: Arnold.
* Parodied in ''Series/{{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 TabletopGame/{{Clue}}do, 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 ''Series/{{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.
* ''Series/{{Scrubs}}'' once featured J.D. playing Connect Four with Death in an ImagineSpot, and Death wins on the diagonal, prompting J.D. to say "Pretty sneaky, Death!" in a parody of an [[http://www.youtube.com/watch?v=WU1K4X_LOxY old commercial]].
* In ''Series/SirArthurConanDoylesTheLostWorld'', 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 [[TakeAThirdOption shoots the hourglass]], making it impossible for the game to end. Death concedes victory to Roxton, and lets them all go.
* In ''Series/SixFeetUnder'', Nate has accidentally taken [[IntoxicationEnsues 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 ''Series/{{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.
* ''Series/TheTwilightZone1959'':
** 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 [[BalancingDeathsBooks 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 and Death gently walks with him into Heaven.
** The 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 the 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 ''Series/TheTwilightZone1985'', "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 from ''Series/TheTwilightZone2002'' 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 ''Series/DoctorWho'' the First Doctor and his companions have to play games against the Celestial Toymaker, who appeared again a few times in the ExpandedUniverse.
* Parodied in a ''Saturday Night Live'' sketch, where Death has given up chess in favor of Trivial Pursuit -- the Baby Doom edition. The categories are: Death, Death, Hell, Armageddon, Death, and Sports.

* 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.
** Music/{{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 ''Film/TenaciousDInThePickOfDestiny''. 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 TrainingMontage 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'
* Music/ChrisDeBurgh's "Spanish Train" is God vs The Devil at draw poker for souls (including that of the trainman, as he realises a little too late). The Devil cheats, natch.
* In the video for "I'll Be Haunting You" by Music/TheyMightBeGiants, a guy who fell off a ladder is challenged by Death to a game of ping-pong. He wins, but [[HereWeGoAgain he dies again due to a falling toolbox, and then prepares to face Death in an actual chess match]].

* 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 Thanatos to a tree and running off.
* Myth/GreekMythology: 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 [[JerkassGods 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 TemptingFate [[BullyingADragon given her]] [[AGodAmI opponent]].
** 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 Myth/GreekMythology, 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 is 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.
* Heracles once challenged Death to a ''wrestling match'' over the soul of his friend's beloved wife, to repay for said friend's hospitality. [[SuperStrength Heracles]] [[DidYouJustPunchOutCthulhu won]].
* From the ancient Myth/{{Egyptian|Mythology}} tales of Prince Khaemwase, the sorcerer-prince Khaemwase Setna went on a quest to find the [[MacGuffin 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 [[FunctionalMagic 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.
* There is an Austrian legend about a drunkard playing ''bowling'' with Death, and in a church to boot! He tried to cheat by throwing a pin out of the window, having bet Death to match his number of strikes. [[TooDumbToLive Guess who was quickly turned into the replacement pin...]]

[[folder:Newspaper Comics]]
* ''ComicStrip/{{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.

* ''Podcast/TheMagnusArchives'': The dying soldier in the folk tale in "Cheating Death" challenges Death to a game. When Death offers him a choice of chess, dominoes and dice, the soldier rejects all of those, takes out his own deck of cards and challenges Death to faro. This is partly he knows that Death must be too good to lose any game that isn't pure luck, and partly because the soldier knows how to cheat at faro. [[spoiler:It turns out that are actually multiple Deaths, each of whom was once a mortal who, upon winning a game against a previous Death, was doomed to take over from them until they find someone who can beat them (which is difficult because they become surpassingly skilled at all games and unable to play badly on purpose). Oh, and it's not just a folk tale - that soldier became one of them.]]

[[folder:Tabletop Games]]
* One route players can take through the inner region in ''TabletopGame/{{Talisman}}'' forces the player to "Dice with Death" by rolling dice against the GrimReaper. If the player rolls higher, the player's character can progress further towards the Crown of Command. If the GrimReaper 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.
* ''TabletopGame/{{Exalted}}'': there is the demon Sigereth, [[RedBaron The Player of Games]][[note]]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[[/note]]. You can issue a challenge to her, either by sorcery or by being a game master of sufficient repute and casting a personally written letter of challenge to her into the sea. You can wager anything you have against her, but if you wager yourself and lose, you're turned into a soulless mannequin. If you win, you can demand something that Sigereth has, including restoring someone who lost to her. 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 Creator/WoodyAllen's short play "Death Knocks", where the protagonist plays gin rummy with TheGrimReaper for the right to stay alive one more day ''and'' a tenth of a cent a point "to make it interesting".
* In Music/IgorStravinsky's opera ''The Rake's Progress'', Tom plays cards with [[{{Satan}} 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 ThePowerOfLove. (Except Nick vengefully inflicts Tom with insanity as he leaves.)

[[folder:Video Games]]
* ''VideoGame/DantesInferno'' begins with the eponymous character getting murdered and the Reaper coming to take his soul. The game's first battle tutorial is the fight between Dante and the Reaper, which ends with Dante ''crushing'' the Reaper and taking his scythe.
* In ''VideoGame/TheSims 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.
** In the original game, you played a game of RockPaperScissors with him. In the event of a tie, the dead Sim was brought [[CameBackWrong partially back to life]], as a Zombie.
*** The [=PS2=] version has a fiddling contest. [[RuleOfCool Never mind that that's Ol' Scratch.]]
* The final stage of ''VideoGame/GuitarHero 3'' is a guitar battle against the Devil for your soul, to a heavy-metal remix of The Devil Went Down to Georgia.
** [[CreatorBacklash Charlie Daniels has]] [[http://www.charliedaniels.com/soapbox-2008/soapbox-2008-040408.htm railed against this version]], because of the possibility--make that [[NintendoHard probability]]--that the player loses (and thus the Devil wins).
* The eponymous character in the old Genesis game ''VideoGame/ChakanTheForeverMan'' 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 BonusBoss.
* In ''VideoGame/{{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 [[BerserkButton killing spirits]].
* In ''VideoGame/TheWitcher'', 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 ''VideoGame/TheWorldEndsWithYou''.
* The main villain of the ''VideoGame/BanjoKazooie'' 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 ''VideoGame/DragonFable'', Ash Dragonblade will, in his storyline, challenge Death to [[SeriousBusiness Tic-Tac-Toe]].
* In ''VideoGame/{{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.
* ''VideoGame/ReturnToZork'''s final showdown puts the player against the BigBad Morpheus in a game of Survivor [[AbsurdlyHighStakesGame for both their own lives and the Kingdom of Zork]]. The game is chess-like and only has two pieces. The Mage Canuk and The Wizard Trembyle, [[HumanChess who actually are those two characters]] that have been [[TakenForGranite turned to stone.]] As well as all the other major magic wielders in the game who's statues blankly observe the contest. If Morpheus wins, the player shares the fate of the others. If the player wins, the spell over the others is broken and [[BigDamnHeroes they use their considerable power to send him back to]]...[[GiantSpaceFleaFromNowhere where is he from again?]]
* In ''VisualNovel/SocratesJonesProPhilosopher'', 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. [[spoiler:Oh, and if he fails, ''both'' of them will become trapped forever in the afterlife.]]
* In ''Witches' Legacy 7: Awakening Darkness'' Jack plays checkers with Death. When Jack wins Death creates a bridge over a chasm so he can continue chasing after Cassandra, who kidnapped his sister.

* ''Webcomic/IrregularWebcomic'' 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, [[Franchise/HarryPotter Quidditch]], [[Franchise/StarWars pod-racing]], and [[Series/{{Mythbusters}} 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 [[AlternateHistory 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, ''Webcomic/{{xkcd}}'' has Gary playing [[http://xkcd.com/393/ D&D with Death]]. He's going to be there a while.
** Aaron Williams neatly reverses the whole thing in [[http://web.archive.org/web/20101216052536/http://crispygamer.com/comics/backward/backward-2009-04-13.aspx this]] Backwards Compatible strip about the death of Dave Arneson
* In [[http://nonadventures.com/2008/06/21/satan-on-the-dock-of-the-bay/ this page]] of ''Webcomic/TheNonAdventuresOfWonderella'', 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 ''[[YouKillItYouBoughtIt takes Satan's place]]''.
* A mild subversion occurred in the webcomic ''Webcomic/ThoseDestined'' : The being claiming to be Death was lying, and had no power to resurrect the protagonist. However, since he had bet his own soul, [[http://thosedestined.pensandtales.com/?date=20041207 his nemesis]] [[http://thosedestined.pensandtales.com/?date=20041209 was more than happy]] [[http://thosedestined.pensandtales.com/?date=20041211 to help]].
* In ''Webcomic/ProblemSleuth'' dead characters are almost always sentenced to a battle with Death in any board game ''other'' than chess. Death will play a board game with you even if you aren't dead. Such as the Game of Life. Death loves Life.
** Although some find it easier to simply [[DeathIsCheap walk out of the afterlife's door]] instead of playing.
* ''Webcomic/ThreePanelSoul'' 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 [[http://www.threepanelsoul.com/view.php?date=2009-02-09 "the ideal method of grilling grilled corn on the cob."]]
* In ''Webcomic/{{Kukuburi}},'' the female protagonist plays battleship with a well-dressed, while tacky, skeleton CardCarryingVillain 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 ''Webcomic/TheOrderOfTheStick'', it all depends on [[http://www.giantitp.com/comics/oots0718.html choosing the right contest]].
* In ''[[http://mortifer.smackjeeves.com 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 [[FanNickname Zebby]] unconscious long enough for Vlad to tattoo his name on Zebidiah's arm, enslaving him.
* In [[http://skin-horse.com/2011/todays-comic-837/ this]] ''Webcomic/SkinHorse'', Tigerlily Jones explains how she won the plans for her ultimate weapon by beating the devil at Jenga.
* In ''Webcomic/{{Roommates}}'', James really just wanted to get a glass of milk (and maybe midnight snack) from the kitchen but got ''[[DidWeJustHaveTeaWithCthulhu invited]]'' to a friendly game of poker by, well, a FairFolk {{Psychopomp}}, a HumanoidAbomination, an AnthropomorphicPersonification of Fear and a StringyHairedGhostGirl of the vengeful type. As he survived the experience they either let him decline or he won, we don't know which he didn't tell.

* In ''Roleplay/TheGamersAlliance'', 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 "[[http://wanderers-library.wikidot.com/for-the-glory For the Glory]]", a story in ''Wiki/TheWanderersLibrary'', a former heavyweight champion challenges Death to a boxing match. He loses.
* In ''Roleplay/SurvivalOfTheFittest V5'', [[spoiler: 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 [[http://amorphia-apparel.com/design/billy/ T-Shirt]], apparently successfully given that it is entitled "...And Billy Lived Forever"
* ''Wiki/SCPFoundation'': [[http://www.scp-wiki.net/scp-1440 SCP-1440]] once challenged Death to a card game for his life, and won. [[FateWorseThanDeath Now he wishes]] [[WalkingWasteland he didn't.]]
* An example which is more PlayedForLaughs than most comes from ''TheAdventureZoneBalance'', in which Kravitz the GrimReaper offers Merle a chance to save Noelle's soul through a quick game of cards. Merle happens to have a deck of cards on him, [[DidYouJustScamCthulhu but it's a cheat deck]].Kravitz doesn't spot the cheat, so Noelle is free to go.
* In ''Webcomic/TheOrderOfTheStick'', winning a contest with Death all depends on [[http://www.giantitp.com/comics/oots0718.html choosing the right contest.]]

[[folder:Western Animation]]
* In "Meatballs or Consequences", an ''WesternAnimation/{{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 [[ExactWords Death interprets as taking all three]], but Death finds them [[TooSpicyForYogSothoth too annoying]] to keep dead.
* The entire reason ''WesternAnimation/TheGrimAdventuresOfBillyAndMandy'' 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 [[HilarityEnsues 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 ''WesternAnimation/{{Futurama}}'' episode "Hell Is Other Robots", the Robot Devil explains that the [[ContractualGenreBlindness 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[[note]]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[[/note]]. 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 [[SubvertedTrope beats the Robot Devil unconscious with the gold fiddle]].
* ''WesternAnimation/DarkwingDuck'' dies in a motorcycle accident because [[CantGetAwayWithNuthin 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 [[UnfinishedBusiness he can defeat the criminal he was chasing.]] The game? Darkwing simply has to do something that Death can't do; he does a cute finger trick with his hands. Death, [[DemBones 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 [[TitleDrop 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 [[RuleOfThree a third, final]] question: [[SerialEscalation 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...
-->'''Hark:''' Open...the window...let the birds... sing.\\
'''Death:''' [[VillainousBreakdown What?! What did you say?]]\\
'''Hark:''' ''(stronger)'' Open the window, let the birds sing.\\
'''Death:''' [[BigNo Nooo!!!]] ''(disappears into the shadows)''
* A NightmareSequence in ''Westernanimation/NightmareNed'' featured Ned playing checkers against the Tooth Fairy in order to keep his teeth.
* ''WesternAnimation/RegularShow'' 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 (that Rigby used previously to beat him), but got away with it.
** This is what happens in pretty much any episode featuring Death. Various characters have defeated him at bowling and hot dog eating contests in order to retain their mortal souls. Probablly this is the reason he started instead to ask them to babysit [[EnfantTerrible his son Thomas]] instead of challenging them in order to let them live.
* On ''WesternAnimation/AdventureTime'' we have [[KidHero Finn]] getting in a ''music battle'' against Death [[ItMakesSenseInContext to save the soul of a plant]].
* Death appears in ''WesternAnimation/ChillyBeach'' to take away Dale, who opts to challenge him and then proceeds to annoy Death by taking too long to pick what game they're going to play. It leads to this exchange:
-->'''Death:''' "CHOOSE! or I shall choose for you!"
-->'''Dale:''' [panicked] "Uh, hockey!"
-->'''Death:''' "Very well." [summons a hockey rink and puck, then proceeds to slapshot said puck into the goal so fast it buns a hole through the net] "...By the way, hockey is what ''I'' would have chosen."
-->'''Dale:''' "Aw, crap."
* The ''WesternAnimation/SouthPark'' episode ''You Have Zero Friends'' has Stan being sucked into Facebook, in a parody of ''Film/{{TRON}}''. Once there, he faces off with his "profile" in a game of...Yahtzee.
* Parodied in the first ''WesternAnimation/FamilyGuy'' to feature Death. While hanging out at the Griffins' trying to work off his sprained ankle, he and Lois play ''[[TabletopGame/GameOfLife Life]].''
-->'''Death:''' [[LampshadeHanging I guess I should find this ironic, but really I'm just bored.]]
* In ''BIONICLE: Mask of Light'', the hero Takanuva confronts the evil Makuta in a Kolhii match (a sport similar to lacrosse) to determine the fate of the Matoran villagers. Unlike many examples, ''Makuta'' actually proposes the confrontation in order to toy with his opponent.
* In ''WesternAnimation/RobotChicken'', Spawn challenges Malebolgia to a fiddle contest. Spawn's act is flawless, while Malebolgia sounds like he's scraping a chalkboard. Unforunately, the demons are the judges, so Spawn loses.
* Parodied on an episode of ''WesternAnimation/{{Kaeloo}}'', where [[TooDumbToLive Stumpy]] challenges the GrimReaper to a rap battle. As the Reaper has actually come for [[spoiler: [[MakesSenseInContext Adele the flower]]]]'s soul and not Stumpy's, he blatantly ignores him.
* A Halloween episode of ''WesternAnimation/PinkyAndTheBrain'' sees Brain challenge one "Mr. Itch" (implied to be Satan) to rhythmic gymnastics for Pinky's soul (which he had voluntarily offered to Mr. Itch in exchange for Brain becoming the ruler of the world) -- but Mr. Itch specifies that if Brain wins, he loses control of the world and can never try to take it over again. Brain goes through with it anyway, and his routine is scored a perfect 10. Mr. Itch barely even tries, but as the judges are his own minions, they give him [[UpToEleven a score of 11]]. The ResetButton is only hit when [[spoiler:Pinky reveals that he actually sold his soul for ''two'' things, one of which Mr. Itch cannot provide, which means the original deal is void.]]