Chain of Deals - Television Tropes & Idioms

I'll trade you a paperclip for a house...

"He traded sand for skins, skins for gold, gold for life. In the end, he traded life for sand."

Character A needs something from character B, but character B wants A to get him/her something from character C, who wants something from character D, etc. etc. etc.

In a comedy, the chain either collapses or is rendered moot at the end. One common way of this happening is that the item the character at the end of the chain received breaks or is otherwise unsatisfactory, and the character decides to take his original bartered-away item back. The next character decides that, if he doesn't get what he wants, he'll take his original item back as well, and so on and so forth all the way back up the chain.

In videogames, this can be an extension ("extension" being the key word) of a Fetch Quest.

See also Fence Painting, Plot Coupon, Sidequest Sidestory and Match Maker Quest. Not to be confused with Chain of People.

Examples:

Anime and Manga

One of the many, many gadgets Doraemon has is a straw that enables a Chain of Deals to give the wielder what they want.

Comics

Occurs in a couple of Carl Barks comics, in particular when Donald Duck's nephews are involved, who seem to be quite good at this. Maharajah Donald starts out as the nephews start with a used-up piece of pencil, they end up with a holiday for them and Donald to India or a country of the sorts. In the end, Donald is captured and will be thrown into a tiger pit. The nephews find a paperclip, exclaiming they've found the thing that can save their uncle. cut to "sometime later", when they trade something very valuable for a truckload of raw meat. They throw it over the wall of the tiger pit, feeding the tigers, thus making them not hungry anymore when Donald gets thrown in.

Fairy Tales and Oral Tradition

Older Than Print: The Japanese legend of the straw millionaire is this trope played completely straight. A poor peasant prays to the goddess of mercy for relief from his miserable life. She grants him a single piece of straw which he trades through his travels until fortunate circumstances lead to the hand in marriage of the daughter of a millionaire.
There're two stories from The Brothers Grimm, both about a boy named Hans; in one, he trades all the way up to marrying a Princess (if memory serves correctly); in the other, he trades all the way down to nothing (but is still happy, because the last thing he traded for was a freaking huge millstone that did nothing but weigh him down).
The Old Woman and the Pig, wherein the old woman implores a whole sequence to do something to the person before them to get the pig to jump over the stile. The last one does so, and the whole cascade ensues.
Old Woman: Cat, kill rat! Rat won't gnaw rope, rope won't hang butcher, butcher won't kill ox, ox won't drink water, water won't put out fire, fire won't burn stick, stick won't beat dog, dog won't bite pig, pig won't jump over the stile, and I shan't get home tonight!
In a Russian fairy tale a rooster choked on a bean. His hen hurried to the housewife asking for some butter to lube rooster's throat, but the woman needed some milk from the cow, who needed the farmer to cut some grass for her, but the farmer needed a scythe from the blacksmith, so the hen ran to the smith, got a scythe and unwound the sequence. Naturally, cynical Russians spoofed the story, so when the hen reaches the blacksmith...
Hen: "Oh, good blackmith, please give me a scythe. Our farmer will cut some grass for the cow, who will give milk, which the housewife shall churn into butter that I will lube rooster's throat with for he choked on a bean."
Blacksmith: "Why sure, I can give you a scythe, but wouldn't it be easier if you just ask me for some butter?"
Hen: "Yeah? And fuck up a cool quest?!"

Film

The Pirates of the Caribbean films tend to enjoy these types of deals and counter deals: in At World's End, Will Turner needs the Black Pearl to rescue his father, but Sao Feng promises it to Beckett; Beckett wants Jack Sparrow's compass, which Will eventually barters with Beckett, though Davy Jones' condition is the murder of Calypso; but the pirates want Calypso alive, and Barbossa wants her released, though Sao Feng thinks he's already captured her... while Jack swans through it all messing up everyone's chains looking for immortality... which he (sort of) had before the pirates came to rescue him because Barbossa needed — oh, you get the point.
In the movie The Comrades of Summer the Russian baseball team needs a new backstop. One of the players steals the coaches Walkman and goes through a series of trades in this style. In the final trade he gets a new backstop and two new Walkmans.
The American Astronaut has Sam, who must return the late king of Venus to his family in Earth, to do so, he must provide Venus with a new king; so he will give the owner of Jupiter a woman and he will give in return The Boy Who Saw A Breast so he can be the new Venusian king. The woman for the Jupiter ruler in turn, is a clon of Eddy, the owner of the Ceres Crossroads who wanted a cat
Marcello Marcello turns this ad infinitum, considering it is supposed to be a Romantic Comedy.

Literature

The Dragaera novel Orca follows this trope, as Vlad has to fulfill a series of deals in order to obtain a cure for a friend.
Neil Gaiman and Dave McKean's children's book The Day I Swapped My Dad for Two Goldfish has the protagonist trade his father for two goldfish, then have to unravel the Chain of Deals that resulted afterwards to get his dad back.
John tries such a chain in Me and My Little Brain after talking to a man who could start with a fifty-cent pocketknife and trade up to a twenty-dollar cow. He manages about nine or ten trades easily, but the chain collapses because he never considered what he would want out of the whole deal. He accepts a piglet as payment in the final trade, but since he can't keep it at home or afford to board it elsewhere, the other boy offers to take it back.
In one of the Henry Reed books, Henry goes to visit an auction, and starting out with some fireplace tools that turn out to be valuable to another bidder who missed them, he parlays the two dollar bid on the tools through to another item and another, until he ends up getting an item and two dollars for his item, finally ending up with two items that the owner bid $40 apiece, a lot of money to Henry. By the time he's finished he's essentially traded things that he ends up getting something worth $100, which cost him nothing because he got the original $2 back during one of the trades.
One Fine Day, an old children's book in which a fox gets his tail hacked off for trying to steal a woman's goods; in order to get it back he has to give her a sewing needle, leading to a chain of deals.
There is a children's story about a woman who wants her son to go to school on time. He refuses, so she tells a cane to beat the boy up. The cane doesn't want to, so she tells a fire to burn the cane. When the fire refuses, she orders a puddle of water to put out the fire, then orders a cow to drink the water when refuses too, tells a butcher to kill the cow, orders a rope to hang the butcher, tells a mouse to gnaw on the rope, and finally tells a cat to eat the mouse, which it agrees to in return for a saucer of milk, and in the end the boy goes off to school. One has to wonder what the moral of the tale is, given that the sociopathic main character callously attempts to orchestrate the deaths of several people, animals and curiously sentient objects just because they refuse to carry out her murderous intents.
This is how the Deveels in Aspirin's Myth Adventures series make their fortunes. The graphic novel even contains a visual representation of a chain of deals that begins with a coat hanger and concludes with a giant ruby.
The well-known Danish fairy tale writer Hans Christian Andersen also wrote a lot of short stories with all sorts of themes and messages — one of these is What Father Does is Always Right (guess the message here) about a man who goes to the market with a horse and makes a long chain of deals, each time lessening the value of his animal/ object and ending up with a sack of rotten apples. He meets a couple of rich Englishmen who make him a wager that his wife will be mad at him for it - however, when he gets home with them, it turns out that she's been insulted by a neighbor, and the rotten apples are just what she needs to get her revenge, and the Englishmen lose the bet.
Example from a forgotten story in a magazine: The protagonist was named Scipio (after the Roman general) and he lived in a small town. His goal for the story required him to trade things with different people in succession with the end result of allowing a collector to complete his prized set of Napoleonic silver plates if the collector did what Scipio wanted him to do. This story of Scipio trading things to accomplish something apparently a regular feature in this magazine.
In the Star Wars Expanded Universe, this is the species hat of the Squibs. The more complex and outrageous the deal, the more prestigious it is.
If You Give a Mouse a Cookie is about the chain of deals that will result if you do what the title says.
Francis Spufford's Alternate History novel Red Plenty has a Soviet black marketeer whose entire business is built on these kind of arrangements.

Live-Action TV

The M*A*S*H episodes "For Want of a Boot" and "The Price of Tomato Juice" both involve variations of this.
- By contrast, the episode "The Long John Flap" features a series of separate exchanges involving a pair of Long Johns, but there's no chain to be unwound.
In Star Trek: Deep Space Nine, this is the B-plots of the second-season episode "Progress," notable for containing the first mention of self-sealing stem bolts, and the fifth-season episode "In The Cards". In the seventh-season episode "Treachery, Faith, and the Great River", we learn that such chains are a tenet of Ferengi philosophy - the "Great Material Continuum".
Nog: There are millions upon millions of worlds in the universe, each one filled with too much of one thing, and not enough of another. And the Great Continuum flows through them all like a mighty river, from "have" to "want" and back again! And if we navigate the Continuum with skill and grace, our ship will be filled with everything our hearts desire!
- Okay... The Ferengi have always insisted they are the best businessmen in the galaxy - this proves it. Nog, You Win Economics Forever!
Stargate SG-1 had one of these in the episode "The Ties that Bind"... which also featured Daniel Jackson as the Butt Monkey.
- To clarify: Daniel and Vala needed to recover an item Vala stole from a former lover so he would reveal how to sever the bond left behind by the bracelets. Doing this involves a Chain of Deals with other people Vala stole from. Predictably, even when they finally get all the items back to their rightful owners, the bracelets' owner reveals that he doesn't know how to sever the connection but he thinks it will wear off...eventually.
A short gag on Sports Night.
Francis in Malcolm in the Middle attempts this to get something or other, and agrees to make exchanges between just about all the loggers in the camp. The problem for Francis is that it's a chain of promised deals, and he keeps making grander and grander promises to try to ground out the chain at something he can manage. He keeps going unsuccessfully until they find out it's rapidly becoming a complete sham and kick the crap out of him.
An episode of Grey's Anatomy features a chain of kidney donations, where patient A's relative will donate to patient B, patient B's relative to patient C, etc. The chain almost falls apart at a number of occasions.
Happens in an episode of Dark Angel as a side note rather than a plot point. Apparently this sort of thing is common given the setting.
Rain attempts to pull one off in order to obtain hot concert tickets (Ron has backstage passes and wants a date with Chelsea, Chelsea wants an appointment with an exclusive stylist which Mallory has, Mallory wants someone to produce a demo tape which Hal can do, Hal will work for food...) in the Naturally Sadie episode "Whose Line Is It Anyway?".
An Episode of Breaker High, Sean and Jimmy need kitchen access from the chef to bake a pizza, who will only give them the key in exchange for a manicure from Ashley in exchange for phone minutes from Alex in exchange for Denise repairing his shorts in exchange for some Dramamine from Max in exchange for Max's Boombox from Captain Ballard in exchange for a written note from Max forged by Tamira in exchange for a picture of Max from Cassidy, who gives it to Sean "for the school yearbook" and takes it back when she realizes what it's really for, causing Sean to continually try shoddy alternatives as the chain falls apart.
Al from Married... with Children did this using a barter system to get a recliner. He unfortunately has to undo it to get back the shoes (the ones he usually sells and what he started the system with) when he finds that his boss is coming for an inspection.
In The Office episode "Garage Sale", Dwight attempts to trade up to "the finest item" at the warehouse Garage Sale via one of these, starting with a single red thumbtack. This is a Shout Out to the "One Red Paperclip" project (see Real Life, below).
- Amazingly, he's able to work his way up to a telescope, which he ultimately swaps with Jim for a packet of "miracle legumes".
On The Unusuals, the B-plot of the episode "One Man Band" involves Casey having to do one favor after another for her fellow cops (each of which involves having to do a new favor for someone else) so she can arrange for a friend of a friend to be sprung on a minor charge. In the end, she does get him out...just in time to find out that he was actually guilty of the hit and run one of the other detective is investigating, which he can now destroy the evidence of.
In Eddie Izzard's three-part series Mongrel Nation, there was a scene where Izzard demonstrated the barter system by buying lunch. Result: this trope.
In the Frasier two-part episode "Semi-Decent Proposal / A Passing Fancy", Frasier wants to go out with a woman named Claire, but is afraid he'll screw things up. He asks Claire's friend Lana to set the two of them up, which she agrees to in exchange for him tutoring her son Kirby to a B- in History. Kirby however, refuses to make an effort, so Frasier promises Kirby that Roz will be his junior prom date if he gets a B (and keeps it a secret from Lana). Frasier then has to get Roz front row seats to a Bruce Springsteen concert in exchange for her cooperation. Naturally, this being Frasier, all the parties involved run into each other at the same restaurant, Lana mistakes Roz for a hooker, and chaos ensues. But after the chain has been unraveled and everyone has stopped yelling, in a surprising turn for a sitcom (where these kinds of incidents usually end up in No Sympathy) everyone just winds up laughing at the ridiculousness rather than staying mad at each other.

Music

The song "There's a Hole in My Bucket'' features a similar situation regarding items needed to fix said bucket. It ends up looping indefinitely:
- A bucket is required, but there's a hole in it. A straw is needed to fix the bucket, but the straw is too long. An axe is needed to cut the straw, but it's too blunt. A stone is required to sharpen the axe, but it's too dry. Water is needed to wet the stone, but it needs to be carried somehow. A bucket is needed to carry the water, but there's a hole in the bucket...

Video Games

Several of the Legend of Zelda games, including Link's Awakening and Ocarina of Time, include an item-trading quest of some sort. The one in Link's Awakening nets you a Magnifying Glass that will allow you to see invisible enemies, get the Boomerang, and reach the Final Boss, while the one in Ocarina nets you the powerful Biggoron's Sword.
- The fan-made game The Legend of Zelda and the Lampshade of No Real Significance has this as pretty much the entire plot.
Suikoden I has a classic example, where recruiting a particular member of the 108 Stars of Destiny requires you to run through a long Chain of Deals in order to get soap for a washing-woman who's run out. When you actually succeed, it turns out that she'd just discovered that she wasn't out of soap after all, but in acknowledgement of the trouble you went through to get her soap, she joins you anyway...
- There's official art of her with a fan of throwing knives between her fingers. That chick was just spoiling for a war or two, but needed to clean her commoner gowns first.
Used in Golden Sun: The Lost Age, where you help a penguin cross a stream and get started in a trading sequence that takes you through every little island on the map, eventually unlocking an area with a bonus boss.
You can do this (with other real-life players) on the GTS in the DS Pokémon games with enough careful thought about what people might be willing to trade. In about a dozen trades, you can exchange a level 6 Magikarp for a level 100 Mewtwo. (As of late, the GTS has had nothing but people offering low-level common Pokemon for level-100 legendaries, and the other way around.)
An old Japanese legend tells of a man who started off with a single piece of straw, and traded up until he was rich. This was referenced in two video games:
- In Shadow Hearts: Covenant, where a sidequest starts off with a man telling the player this story and giving them a straw. Eventually, the player can trade this to get the Infinity+1 Sword for one of the characters. To be fair, it's a pretty, yet magical, steel fan, unless the player makes a wrong trade and ends up with worthless junk (or a small fortune in cash).
- The legend is referenced and subverted in Saiunkoku Monogatari, where a character is given money to buy ingredients for dinner, but ends up with a Chain of Deals ending in a single piece of straw.
Animal Crossing occasionally forces you to go on a variant of this, in which an animal wants to get an item back from another one who borrowed it... but then you go there and discover that that animal lent the item to someone else. You have to keep following the item until you get it and can bring it back to its owner.
- It can get really weird when half the village is sharing the same handkerchief.
A quest in Kingdom of Loathing has you getting caught in one of these while trying to get some stolen comic books back for the Gnomish Gnomads. Not only is the quest optional, the reward sucks. It also refers to the Real Life example above: the only item you actually retrieve yourself is the big red paperclip in the Haiku Dungeon.
The trickiest puzzle in the original Final Fantasy I is basically a chain of deals, the difference being that not all the trades are deliberate. (For example, you perform one "trade" by showing the Crown to Astos, killing him, and taking Matoya's crystal off his corpse.) This sequence is necessary to advance in the game; in fact, it all takes place before the first fiend.
- In the Dawn of Souls remake of the game, there's a Chain of Deals puzzle that involves trading things between a bunch of dwarves in order to progress in a dungeon.
All the Mega Man Battle Network games have NPCs who want to trade BattleChips with you. Most of the trades are standalone, but in games 3 and 6, you can make several successive trades to obtain a powerful chip.
- You can screw the chain up in 6 by dumping one of the in-between chips (DublShot C) in the trader; it's almost impossible to get another one in C code. This sounds like a hard mistake to make — who puts their last one of something in the trader? — but the BN6 boards at GameFAQs get more threads asking about this than anything else.
Ogre Battle has at least one of these in the series. The original SNES game, Episode IV, March of the Black Queen had several. The first you see is the powerful Ring of Undead, held by a wizard early in the game who would trade it for a Lexicon of Undead. And then there is the Diaspola chain. You start with some pirates with a copy of The Saga who are looking for a Map, which is in town with a man who is looking for Amatsu that can be found in the trade shop of neighboring town who only buys Furs which an underhanded sneak has and will part ways with if you give him all you money or return his stolen goblet held by bandits who want to hear a Foul Tome you received from a previous stage. Each of these items is worth progressively more than the previous.
The desert monkey cave in Earthbound is basically a Puzzle Chain of Deals. With some lampshading thrown in ("amongst all these doors..."). Thankfully it's funny. Some players still consider it the most frustrating part of the game, mostly because every room looks like every other room and one item turns into something else (thus rendering it useless) after too much time passes. Fortunately, the player's guide (which was originally packaged with the game) eliminated most of the frustration by providing maps.
Secret of Evermore's greek market blatantly uses this, though it's entirely optional. It's even pretty complex, with multiple traders giving the same item for different exchanges, but the rewards you can get through it are items that permanently boost your abilities, so it's worth your time and resources.
Romancing Sa Ga involved a large trade quest kicked off when Strom (Water Elemental Lord) demands the "Raincloud Armlet" in exchange for a captive princess. It's in the possession of Adyllis (Earth Elemental Lord), who will only give it up if you give him the Cyclone Shoes, which you can only get by trading the Ignigarde Helmet to Avi (Wind Elemental Lord) by acquiring the Ice Sword for Pyrix (Fire Elemental Lord) in which you must plunk down 20,000 gold or by killing a recruitable character. At any point in the chain, you can decide to brute-force the whole thing and just beat the crap out of the dragon, though and you get an awesome shield as a Item Drop. However that does have some repercussions, by killing Strom you cannot get the optimal amount of jewels for doing the quest normally, are unable to do his Ecology Quest and also getting the chance to fight his Corrupted Form; Slask (Item Drop is the Chaosbringer; A powerful 2 Handed Axe that gives an Intellect boost). This also bars you from exploring his temple later, meaning that you can't get the items inside — including the Water Spirit, which is required for another quest with fantastic rewards. Also there is a trading ability for you to use in which you can trade items with monsters; so a mini Chain of Deals is possible; Sidetracked by the Gold Saucer indeed...
- Actually if you trade with monsters enough, they become "Crowned" which means they are stronger but give better Item Drops. Also trading with monsters can net in quite a bit of jewels or cash if you trade correctly.
This is how you get the Infinity+1 Sword in Alundra 2.
The MMORPG RuneScape has an infuriating quest of this type called One Small Favor. By the time your character is halfway through building the very long chain of trades, he/she starts lampshading the ridiculousness of the whole thing. In the end, the original quest-giver doesn't seem to think getting him the original favor was such a big deal as to warrant a reward until your character goes off on him.
- Somewhat worthwhile though, a new recipe for a potion and 20000 free exp. Nothing to scoff at to an extent.
  - And a keyring, which is far more useful than it sounds.
- To clarify: this quest involves trading favours through twenty steps, culminating in fixing a gnome's runway lights after basically trekking in a complete path around from Port Sarim through almost every other area on the map and ending up on the other side of the world, and then going back. Then the ungrateful bastard who gave you the quest doesn't even give you a reward until you explain what you had to go through for some goddamn logs.
- There's also one part of the Fremmenik Trials quest. You end up talking to basically everyone in the entire village until you talk to someone who just wants 5000 gold.
  - Which, while irritating, is still better in that you never have to leave the village.
One of the subquests in Wonder Boy In Monster Land is this; start with a letter and finish with either a solution to the final dungeon (very handy - that place is a non-logical maze) or a trinket that will take off about a third of the final boss's health instantly (even more handy - if you're properly kitted out, the final boss isn't difficult to kill, making running out of time the biggest problem).
A rather extensive example occurs in the original Paper Mario, where you deliver letters and get letters in return with the help of Parakarry. The errand has you deliver letters to NPCs from Chapter 1 to Chapter 7, and completing the sidequest nets you the Lucky Day badge, an item that greatly increases evasion.
- In Super Paper Mario, Merlee wants a crystal ball from Merluvlee, who in turn wants a training machine (actually a DS) from Bestovius, who in turn wants a mysterious DVD (implied to be porn) from Watchitt, who wants an autograph from Merlumina, who wants to go to sleep. Eventually, her long speeches bore you to sleep, causing her to get sleepy, leading to you completing the chain. Merlee repays you with a free curse and a key that allows you to unlock the Pixl Piccolo.
- Similar side-quests also happen in the first two games, both of them involving the aforementioned "secret DVD" (originally a tape). My, what lazy censors.
Browser-based MMORPG Travians includes several of these, and finally throws in a Lampshade Hanging:
Tombo: Oh, you're up to your strange swapping deals again?
The old game Hacker required you to send a robot around the world trading items to obtain pieces of a secret document, while figuring out how to avoid the security checks on the system you were "connected to".
Planescape: Torment: You want information on Ravel? OK, you just need to talk to Ecco, except she won't talk to to you at all, so maybe you should talk to Dolores who doesn't want to talk to you unless you get something from Merriman, who wants to forget, so you need to get a Stygian shard, which you can't pick up without a very special cup that you can get by curing a wizard-reject's alcoholism. Oh, yeah. You have to figure out half of these on your own too.
In the Age of Empires 2 Mongol campaing, the first scenario involves you riding around trying to coax several different tribes to join you (except one, which is stated as being 'without honor' for no apparent reason). Most of these tribes ask you to do something for them in exchange, often something you can't do until a different tribe joins you. For example, one tribe wants you to bring them a relic, and only monks can carry relics, so you have to get the tribe that gives you monks to join first.
Dark Cloud has one of these. The chain begins with a pink lollipop and ends with the single most powerful weapon upgrade attachment in the game.
Jay's Journey has one spanning most of the game, most (but not all) of which is required to complete the game. Jay sees the trope in progress and is more than happy to make bad deals, because he knows it'll all work out in the end. (He gets a bit annoyed when NPCs are slow to give rewards, or when one NPC tries to steal the trade-item-of-the-minute, however.) All of the items have an identical description: "Some trade item".
Breath of Fire IV has this, too. In fact, it's needed for one of Ryu's Dragon forms.
Dungeon Siege II has a chain quest that spans virtually the entire campaign.
Dr. Doom does this behind the scenes in Marvel: Ultimate Alliance, and you spend the entire game trying to catch up.
In Family Project, Chunhua gets a free piece of candy on the street as an advertisement and gives it to Tsukasa. Tsukasa trades it for a pack of cigarettes. He gives the cigarettes to a guy on the street and gets a 5000 yen gift certificate. He uses that to pay Masumi's debt at some store or another, and she gives him thirty lottery tickets, enough for three tries at a game. Chunhua tries three times and eventually gets a personal computer worth 300,000 yen. Lampshaded.
One of these shows up in Final Fantasy Tactics A2; you're not doing the Chain of Deals, rather you're one of the people in it. You get to see the guy royally screw it up: The step is adamantite for a vial of silver liquid... and silver liquid melts adamantite on contact. Poor sap forgot to wash his hands.
Russian quest game ""Last Year's Snow Was Falling'' had a subversion of that. Once you understood the 5-step chain of deals and tried to grab the starting item, you were carried away to the next location.
In Dubloon, you must trade items on Stern Island to get the map location of East Sea Serpent.
Due to the introduction of player-to-player trading, Team Fortress 2 can have thousands of people simultaneously attempting various self-invented chain-trades. In order to get a certain hat for your friend, you have to go to someone else who has that hat, and who wants some other hat that you can get from another friend, etc.
- Some players have done Red Stapler trading sequences, often managing to climb from a crate to something incredibly valuable.
- There is actually a whole theoretical model built upon this: Various players do things called "Scrap Banking". For Scrap Banking, the Banker pays 1 scrap for any 2 weapons. In the crafting system, 2 weapons can be turned into 1 scrap if they are from the same class, so in theory the Banker is not loosing any "revenue". He then sells the Weapons for 1 scrap each, effectively doubling his scraps with each pass. Any unsold items are crafted into scraps, combined with the others and re-"banked" into more weapons. Rinse and repeat. The problem with this, however, is that any player that can trade (those who have gotten a full version of the game) knows the values of expensive weapons, and would attempt to sell them on their own. The only weapons they'd scrap bank are ones everyone already has, or are widely abundant. This means that very rarely will this work, and if it works, it's only going to net you a very, very low net gain for the effort you put in.
- With the introduction of Steam Trading, you can now potentially trade up from a lowly, common crate all the way up to a $60 dollar game like Deus Ex, provided you get lucky enough and find the right buyers.
Edutainment Game Spanish for the Real World has one activity where the player is given a basket of fruit and a list of (different) fruits s/he is supposed to get, and must trade with the various people at the market for them, leading to this trope. (For example, you have an apple and need to get an orange. However, the person who has an orange only wants a banana, so first you have to trade with the person who has a banana, who wants two lemons, so first you have to trade with the person who has lemons...)
The Spirit game, Spirit: Stallion Of The Cimarron: Forever Free features one near the end. In exchange for a horse's freedom, someone wants a wheel to fix their cart, the blacksmith who has a wheel wants a blanket from Little Creek, Little Creek in turn wants an axe to chop wood with...and said axe can then be ~~stolen~~ taken from Snakefinger.
This can happen between three or more players in Heroes of Newerth's and other DotA clones' Single Draft mode where every player is given a choice from three random heroes that can be swapped between other players in your team.
In the first series of .hack, one of the least favorite side-quests was to help someone with their trading service, which quickly went horribly wrong because nobody can do an even trade, and one more item had to be fetched in order to even start the chain of deals. Everyone lampshades how irritating this is.
An obscure point-and-click adventure entitled The Day The World Broke has a doozy of a chain. To get Carbine the half-Lizard, half-camera (all the non-human characters are half-animal, half-machine) to stop standing in the path of an element valve, which is causing chaos across Earth's surface, you need to fix his lens. The only place to get a lens is the Glass Works, where Carbine doesn't have the best reputation. That's a moot point, though, as the Glass Works is too busy filling orders for new glassware for Lugnut the bartender. So you need to get a note from Lugnut, who'll give it to you in exchange for getting rival bartender Decanter to part with rare bottle of sludge. In order to get that, Decanter wants a recording of a song his mother used to sing him, which requires an instrument that's notoriously difficult to find but fortunately is in the hands of one of Lugnut's customers, Ratchet, who will trade it to you for another instrument which actually doesn't exist, so you need to enlist the help of Phlange, who will help you make something that could pass for it, but in order to get Phlange to help you, you have to get her to stop standing in a different element valve. To get her to do this, you have to call Julius and Bud at Mission Control, who will finally convince her to leave, allowing you to get her help to make the instrument to trade for the other instrument to trade for the recording to trade for the sludge to trade for the note to trade for the lens. Whew.

Web Comics

Parodied here by 8-Bit Theater.
Skin Horse features an increasingly absurd chain as main character Tip tries to deal with an increasingly bizarre string of escaped/lost sentient lab experiments.
- Which proves to have some consequences, since he ends up screwing up the whole chain of deals his boss was used to dealing with - which results in her having to find out if the new leadership down in the basement is amenable to talking with the folks upstairs. Lampshaded at several points during the whole chain.
Slightly Damned provides its take on these.
Featured in Gold Coin Comics, starting here, where it begins with a crappy belated birthday card.

Web Original

The SMBC Theater sketch Internet Bartering parodies the One Red Paperclip example nicely.
Episode 9 of My Little Pony The Mentally Advanced Series. Twilight needs holy water from Pinkie, who wants vengeance on Fluttershy, who wants her hairbrush back from Rarity, who wants Applejack to lend her some farm hands for her work. Eventually Subverted: in the end, Twilight can't remember who wants what or why, and instead gets some holy water from the mayor.

Theater

This is kind of the plot of the musical 13.

Western Animation

The Ed, Edd n' Eddy episode "Who, What, Where, Ed!" featured a Chain of Deals that started with Eddy trying to get a chicken egg from Rolf, who wanted sawdust they had to borrow from Kevin, who wanted paint they had to borrow from Jimmy, who wanted clams they had to borrow from Johnny, and so on, driving Eddy closer and closer to insanity (as well as Lampshade Hanging) with every turn. The chain goes to Jimmy twice, they're forced to get something different from Johnny than he first asked because they couldn't get it from the Kankers, and eventually stretches back to Rolf. And while the Eds finally resolve the chain, Ed breaks the egg the second they get it because he thought he needed to set the chicken inside free.
In one of the "Lord Bravery" segments of Freakazoid!, Lord Bravery is given a Cease-and-Desist order on his name, as it was first used by a bakery. As it turns out, the bakery resorted to Lord Bravery because the name the owner wanted to use was already taken. The owner offers to give Lord Bravery back his name if the owners of the business with the name she wants will give it to her. This leads to a ridiculously long chain of businesses with ludicrously inappropriate names that ends only with the discovery of a shop owner who is quite happy with his business' name, causing the chain to collapse.
- And forcing Lord Bravery to change his monicker to Lord Smoked Meats And Fishes, making people respect him even less than they did before.
This was also the basis for the Looney Tunes short Leghorn Swoggled, with Henery Hawk making a long string of deals in order to catch Foghorn Leghorn. After making a bunch of deals (dog wants a bone, cat knows where to get a bone but wants a fish, mouse knows where to get fish but wants cheese) he remarks "I wonder what the cheese will want?"
- Also happens in Dime to Retire, where Daffy runs a scam in the hotel Porky is staying at. First, he let a mouse into Porky's room, which drove Porky nuts by eating a piece of celery, prompting him to have Daffy bring in a cat to chase it off for a mere $5, only for the cat to refuse to let him sleep on his bed, thus Daffy brought a dog to scare it away for $10, only for the boxer (after hearing a bell, courtesy of Daffy) to start punching Porky, after which Daffy charged $26 to bring in a lion to get rid of it, which naturally tried to eat Porky, then for another $72, Daffy used an elephant to drive out the lion, however, the elephant then took up most of the room, so for $666, Daffy released the mouse back into Porky's room to scare it off, leaving Porky with the celery-eating mouse all over again.
The Life and Times of Juniper Lee, "It's the Great Pumpkin, Juniper Lee": June manages to successfully complete a Chain of Deals to un-spell a few monsters. One of those "deals" involved winning a wrestling match.
In an episode of Recess the gang arrange a Chain of Deals to enable Mikey to achieve his dream of becoming a crossing guard. The chain works perfectly, but when it starts to rain Mikey decides he doesn't want the job after all.
Parodied on Two Stupid Dogs. An off the hook payphone tells the dogs to get a quarter, so they go to a change machine, but they need to get a dollar. This leads them on a quest to get larger and larger sums of money, each of which is eventually traded in for a smaller amount right down to the quarter.
- Which is then used to phone the larger dog, in prison with a $10,000 bail.
Chowder goes through a Chain of Deals to retrieve his lost hat, but accidentally gives the hat away in the process, requiring an undoing of the chain... and a redoing... and another redoing... and it's all done in song. (Lampshaded at the fourth stop, when a giant says "I'm beginning to see a pattern here...")
In an episode of House of Mouse, after accidentally spending the rent money on cheese, Mickey is in desperate need of $50. Merlin will give Mickey $50 in exchange for a sword for Arthur, The Headless Horseman will give Mickey a sword in exchange for a pumpkin to use as a head, Cinderella will give Mickey a pumpkin in exchange for an alternate ride home, Aladdin will give Cinderalla a carpet ride home if he can get a rose for Jasmine, Beast will give Mickey an enchanted rose in exchange for a book for Belle, and Yen Sid is in no mood at all to share his books, scaring Mickey off and throwing the whole chain apart.
A U.S. Acres segment in Garfield and Friends had Orson wanting to get Bo a record player. Booker has one but wants a skateboard. After failing to hit Roy's three practical jokes, one of which involved super-hot chewing gum, Orson convinces Roy to part with his skateboard in exchange for a pie. Lanolin is willing to give up her pie for a stepladder. Wade is more than happy to get rid of his stepladder, but Orson insists on giving him something... specifically, the spicy chewing gum he got from Roy. When Wade realizes how horrible the gum is, he takes back his ladder, causing the whole chain to temporarily reverse.
An episode of Jimmy Two-Shoes had Jimmy go through one to get Beezy's collection of chewed gum back.

Real Life

Wondering about the page picture? As documented on One Red Paperclip, in the course of one year (July 2005 to July 2006) Kyle MacDonald negotiated a Chain of Deals that started with a single red paperclip and ended up with a house — in only fourteen trades! And now he's putting the house up for trade. Someone get this man the Infinity+1 Sword.
- Incidentally, he borrowed the paperclip back. To bend into an engagement ring to propose to his wife.
The impracticality of this is one of the major reasons (the others being transportability and storability) for introducing currency*
Or currency spontaneously arising in the form of a good accepted as such by custom, like precious metals or salt
, as opposed to relying on barter for trade. With barter, you have to find someone who both has something you want and wants something you have in order to make a trade, while with currency you only have to do the former because you know almost everyone will want currency.
- Star Trek reviewer SF Debris went into this topic at some length while reviewing a DS9 episode about a Chain of Deals. He pointed out that although the Federation claims to have eliminated money and the need for money, clearly people still have needs or desires that cannot be met except through exchange of goods and services, and that the absence of an accepted currency just makes the whole thing wastefully inefficient and even comical. He also points out an Accidental Aesop: Since Jake has never used money, he has no comprehension of its value, which is why he thoughtlessly badgers his best friend into trading away several years' worth of savings on a baseball card.
In the residential housing market, many sale contracts are conditional on the buyer's current home being sold. This means a situation can arise where the sale of a home is dependent on the sale of another home, which is dependent on the sale of another home, etc. making for a very long chain of held up contracts. When the last seller finds a buyer who is not tied to selling a current home, the entire chain of contracts go through very quickly thereafter.
Without getting into specifics, players of any kind of Collectible Card Game (or, indeed, collectible anything-that-comes-randomly-blind-packed game) have likely committed to a three-or-more-way trade in order to get that last card for their precious deck/army/complete expansion set.
Interestingly, electrical power systems are often protected by a chain-of-deals-like system. In interlocking, you must satisfy certain conditions in order to operate an item of equipment (disconnectors, earth switches, access gates etc.) which involves following prescribed sequences of opening/closing switches to obtain keys to access other sequences to obtain another key that opens the shutter to the hand crank you need to operate the item of equipment you were interested in the first place. For added super-bonus fun, on offshore windfarms certain steps entail sailing between individual turbines, key clutched in hand. The reason for this intentional complexity is to ensure that all equipment is made safe before anyone gets anywhere near it, and that there is no danger of damaging the main grid.