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== [[Film]] ==
* In one of the Danish ''[[Olsen -Banden]]'' movies, the titular gang of heroic thieves are working for a [[Corrupt Corporate Executive]] who owns an insurance-company, tasked to steal a [[MacGuffin]] containing sensitive information for him. Once they retrieve it, however, he decides that it would be cheaper to just kill them and take the [[MacGuffin]], rather than pay them the two million he promised. Narrowly escaping an attempt on his life, Olsen - knowing that nobody ELSE would be willing to pay for the information - comes up with a plan: He takes out a life-insurance with the company, with a 2.000.000 payout. Thus, it would no longer be economical for the Corrupt CEO to kill him, since it would cost as much as negotiating, while involving more dangers. But when he shows it off to the CEO, he just laughs and points him to the 'small print', which shows the exceptions to the policy, many of which could be easily used for arranging an 'accident'. Cue Olsen tied up on a conveyor-belt over a vat of acid.
 
== [[Literature]] ==
* In one of the ''[[All Creatures Great and Small (TV)|All Creatures Great and Small]]'' books, the narrator tells about some brothers and father who got slick talked into disability insurance. However, the joke was on the insurance company as they "managed" to somehow get injured repeatedly at an amazing rate as soon as the policy was issued. They remarked how it was strange how the company dropped them as soon as the policy term ran out but that they got another company, albeit at a higher premium, to insure them.
* [[Douglas Adams]] once suggested that insurance companies have [[Time Travel]], which is why whatever happens to you is mysteriously excluded from the policy ''and always was''.
* In ''[[Discworld (Literature)/Guards Guards|Guards Guards]]'' Dibbler promises that his "dragon protection" cream will save you from being burned to death by dragon flame, and if it doesn't work then you get your money back (upon personal application only).
* An insurance company ''thought'' they were doing this, when they sold a policy to a young seaman in Tom Holt's ''Flying Dutch.'' But then he became the imortal captain of the Flying Dutchman, and after living to the impossibly old age that the policy required before it made any payout, the payout ''increased'' each year he survived beyond that. Now, if he dies, the insurance company is on the hook for more money than there is in the world, and through a variety of mergers, and such, they've distributed the risk to every bank and insurance company in the world, so they need him to go on living forever, or his death will destroy the entire world's economy.
 
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** In "The Canal" Baron Seagoon insures his nephew Neddie against various unlikely fatal accidents - all of which he has of course arranged. The [[Running Gag]] is that Neddie always manages to escape ''just'' before the Baron can collect.
** In "Insurance, The White Man's Burden" Grytpype and Moriarty persuade Neddie to take out fire insurance - on the English Channel. This backfires when Coastguard Crun pours oil on the sea to calm the waves during a rescue and then burns it off.
* In ''[[I'm Sorry, I'll Read That Again (Radio)|I'm Sorry Ill Read That Again]]'', a character gets insurance against being trampled by a herd of bison in Whitehall. He immediately gets trampled in Whitehall ... by a herd of ''buffalo''.
* On ''[[Hello Cheeky (Radio)|Hello Cheeky]]'', there's an insurance policy that has you covered if you're kicked by a stag in the London underground or stabbed by a Guatemalan midget in church. "Remember the name...Furtive Insurance! Our motto -- take the money and run."
 
== [[Web Comics]] ==
* George in ''[[El Goonish Shive (Webcomic)|El Goonish Shive]]'' has car insurance that [http://www.egscomics.com/?date=2011-01-14 covered monster-related damage] (obviously just to advertise "completeness"). The result: surprise, they have to pay for repairs of a car damaged in fire monster's attack (and on camera at that).
* Occurs in ''[[Exiern]]'' [http://www.exiern.com/?p=160 here], but even when you get the best of that demonic lawyer, [http://www.exiern.com/?p=172 just try cashing in that policy]. When it comes to insurance companies, [[Failure Is the Only Option]].
 
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* When ''[[The Simpsons]]'' go to Italy, their car gets hit by Mortadella cheese falling off a cheese truck. They got the cheese insurance, but it doesn't cover Mortadella.
* In the ''[[Looney Tunes]]'' short "Fool Coverage", Daffy is an insurance salesman trying to sell Porky some life insurance. He promises the policy will pay Porky one million dollars for a black eye... provided it was the result of an elephant stampede happening in his house between 3:55 and 4:00 PM on July 4 during a hailstorm. At the end of the cartoon, that is ''exactly'' what happens! To try to save face, Daffy adds "and a baby zebra" to the clause. Cue baby zebra.
* This is the plot of the ''[[NedsNed's Newt]]'' episode "Trouble Indemnity". The insurance agent doesn't even need to hide anything in the fine print - Ned's parents are dumb enough to insure a seashell rabbit statue from being stolen by a weasel, a novelty mirror from being broken by a Russian dancer, and a broken record from being welded back by an earthquake (as well as a lot of other stuff.) Newton's [[Shapeshifting]] skills come in handy when sending that business back at the unscrupulous insurer.
 
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