In TV Land, collecting on an insurance claim can be something of a crapshoot. It's all right there in the fine print: your flood insurance only pays out for damage caused by tidal waves, your car insurance only pays out for damage caused by post-apocalyptic punk bikers, your life insurance only pays out if you're [[Series/DeadLikeMe killed by a block of frozen toilet waste falling out of an airplane]], your health insurance only pays out for diseases contracted from rabid guinea pigs...

If someone says they're insured - especially if it's ''important'' that they're insured - more often than not, it's going to turn out that their insurance is of this variety, and getting the insurer to pay out will be like getting blood out of a stone. On rare occasions, things will align ''just right'' that the insured can make their claim without the insurer being able to weasel out of it on a technicality; this is more likely to happen the more money (and comedy) is involved.


[[folder: Advertising ]]

* In one insurance commercial a tree falls on a couple's car and they nervously call their insurance company to make a claim. The operator tells them their low rate plan only covers damage from a [[ ficus]]
** In another for the same company, a man finds the name "Brad" keyed into his car, but his policy only covers full names. If it had been "Bradley" or even "Brady," it would have been fine.


[[folder: Anime/Manga ]]

* Towards the end of ''Anime/{{Trigun}}'' the Bertinelli Insurance Company (which is the boss of Meryll and Milly) simply decides to use its political power to call off [[WalkingDisasterArea Vash The Stampede's]] sixty-billion double-dollar bounty and declares him a "[[PersonOfMassDestruction walking Act of God]]", legally washing its hands from paying for any (and that is ''any'') kind of damage that Vash's adventures (and the Gung-Ho Guns' relentless campaign to kill and/or demoralize him) cause.


[[folder: Comic Books ]]

* In ''ComicBook/JudgeDredd'', pop sensation Pug Ugly is murdered on stage, and the perp is killed while resisting capture. It turns out the guy had taken out dozens of life insurances on himself, planning to get killed to make his mother rich. Unfortunately, Mega-City insurance companies always include the standard "claim void if killed by a Judge on duty".
* One Disney comic had Rockerduck (Scrooge's business rival) insure a box of cigars for a massive policy, with one of Scrooge's insurance agencies. (Scrooge is forced to accept it, though he objects loudly.) Rockerduck at first suggest smoking the cigars to cash in the policy, but fortunately Scrooge points out that intentional fires constitute grounds for fraud (or that intentionally lit fires aren't covered by the use of the word "fire" in the policy.) However, putting the box in a pine house in the middle of a pine forest during thunder season is perfectly legal.
** [[FridgeBrilliance Scrooge's interpretation of the insurance policy is exactly how just about every policy involving "fire" is interpreted.]]
* In ''ComicBook/DaredevilBornAgain'', after Nuke's rampage through Hell's Kitchen the owners of a diner Matt had been working at say that they insurance company refuses to pay their claim, and they don't have the money to hire a lawyer. Since Matt has been disbarred, he takes some cash from a group of criminals he beats up to help repair the diner.


[[folder: Film ]]

* In one of the Danish ''Film/OlsenBanden'' movies, the titular gang of heroic thieves are working for a CorruptCorporateExecutive 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.
* A major plot point in ''WesternAnimation/TheIncredibles''. Mr. Incredible got into trouble with his boss at an insurance company for helping claimants maneuver their way through the system.
* The plot of ''Film/TheManWhoSuedGod'' starts because the protagonist's boat got destroyed during a storm and his insurance company refuses to pay since the storm was an "act of God".


[[folder: Literature ]]

* Not surprisingly, [[Series/AllCreaturesGreatAndSmall James Herriot]] had a few brushes with this sort of thing:
** In one of the 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.
** In another book, we learn that most farmers have insurance that covers their cattle against death from lightning strike, but the insurers require a letter from the vet confirming the cause of death. Every time the weather turned thundery, the practice had to deal with farmers who were absolutely convinced in the face of all evidence to the contrary that their prize cow had keeled over dead from being struck by lightning, not heart failure or some other unfortunate malady. Evidence such as, say, candle wax mysteriously appearing on the dead cow at the site of the burn.
* Creator/DouglasAdams once suggested that insurance companies have TimeTravel, which is why whatever happens to you is mysteriously excluded from the policy ''and always was''.
* In ''Discworld/GuardsGuards'' 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 ''Literature/FlyingDutch.'' But then he became the immortal 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 failing that, name the insurance company as inheritor), or his death will destroy the entire world's economy.
* In "Framför Rubrikerna" (Roughly; "In front of the headlines", a collection of amusing newspaper clips), author Stellan Sundahl notes that he heard about a guy who bought a combined theft & fire insurance to his car. Turned out it was only valid if someone stole his car ''while'' it was on fire...
* In one of Literature/SecretCity short stories there's a very successful insurance company. In setting with FunctionalMagic they hired best of the best for their divination department, so that they can exclude particular cases from their contracts or just refuse a particular client, because he will be eligible for payment later. Too bad for them, that Dark Court is even greedier and blocked all prediction spells concerning salesman, who participated in their scheme, which got his business damaged.
* One character in the Creator/TimDorsey novel ''Florida Roadkill'' is an insurance executive who specializes in rejecting claims, ''especially'' if they're about something covered in the actual policy. He ends up getting shot and dies when his request for treatment is rejected because the HMO routes the request for payment to his office.


[[folder: Live Action TV ]]

* An episode of ''{{Series/Dinosaurs}}'' had the Sinclair's house (and TV) struck by a falling meteor. Earl actually had bought meteor insurance but was denied coverage since he was only covered for meteors and once a meteor passes through the atmosphere it becomes a meteorite.
* In the [[ "Motor Insurance Sketch"]] from ''Series/MontyPythonsFlyingCircus'', a vicar had bought some insurance and has now come to collect on it.
-->'''Vicar:''' It's about this letter you sent me regarding my insurance claim.
-->'''Devious:''' Oh, yeah, yeah - well, you see, it's just that we're yet...totally satisfied with the grounds of your claim.
-->'''Vicar:''' But it says something about filling my mouth in with cement.
-->'''Devious:''' Oh well, that's just insurance jargon, you know.
-->'''Vicar:''' But my car was hit by a lorry while standing in the garage and you refuse to pay my claim.
-->'''Devious:''' Oh well, Reverend your your we are. It states quite clearly that no claim you make will be paid.
-->'''Vicar:''' Oh dear.
-->'''Devious:''' You see, you unfortunately plumped for our 'Neverpay' policy, which, you know, if you never claim is very worthwhile...but you had to claim, and, well, there it is.
* One of Dennis Dugan's scams on ''Series/ThirtyRock'' is suicide insurance.
* Inverted in ''Series/HomeImprovement'' when Tim tries to collect insurance on Jill's car after he dropped a 3-ton I-beam on it. Tim is so [[TheKlutz disaster prone]] that he gets into accidents that would normally fit ImpossibleInsurance, but not regular insurance.
* In ''Series/BreakingBad'', Walter White has health insurance via his employment as a teacher--but it won't pay for the chemotherapy he needs to treat his cancer, setting in motion the events of the series.

[[folder: Magazines]]

* The Magazine/{{MAD}} parody of ''Highway to Heaven'' used this trope.


[[folder: Newspaper Comics ]]

* In ''TheGambols'' Gaye takes out a travel insurance policy that she is told will pay out a million pounds if she hurts herself on the England-France ferry. Which technically it does, but only if the injury is ''"hit by a meteorite while lying on the sun-deck"''. Personal application only.


[[folder: Radio ]]

* There are a number of examples in ''Radio/TheGoonShow'', eg:
** In "The Canal" Baron Seagoon insures his nephew Neddie against various unlikely fatal accidents - all of which he has of course arranged. The RunningGag 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 ''Radio/ImSorryIllReadThatAgain'', 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 ''Radio/HelloCheeky'', 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."


[[folder: Web Comics ]]

* George in ''Webcomic/ElGoonishShive'' has car insurance that [[ 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 ''Webcomic/{{Exiern}}'' [[ here]], but even when you get the best of that demonic lawyer, [[ just try cashing in that policy]]. When it comes to insurance companies, FailureIsTheOnlyOption.
* Odd, and incredibly greedy example from ''WebComic/DarkLegacyComics'' [[ here]]. Keydar's insurance doesn't actually cover anything, they just take a monthly fee.
* In ''WebComic/DominicDeegan'', Donovan manages to get injury insurance for only half of his children. [[ Their upper halves]].


[[folder: Western Animation ]]

* When ''TheSimpsons'' go to Italy, their car gets hit by Mortadella falling off a cheese truck. They got the cheese insurance, but it doesn't cover Mortadella.
** This counts as ''FridgeBrilliance'' since Mortadella isn't a cheese, it's a type of sausage.
* In the ''WesternAnimation/LooneyTunes'' short "Fool Coverage", insurance salesman Daffy Duck convinces Porky Pig to buy an accident policy that pays 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 p.m. on the Fourth of July 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. [[CueTheFlyingPigs Cue baby zebra]].
* This is the plot of the ''WesternAnimation/NedsNewt'' 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.
* ''WesternAnimation/GarfieldAndFriends'': When Jon Arbuckle had a car crash, the insurer's only show of efficiency was at raising Jon's monthly payments. The insurer then required several documents and, for last, the car. ComicStrip/{{Garfield}} and Odie, as a result of trying to get food from the car, accidentally crashed it at the insurer's office. After paying for the car's repairs, the insurer tried to collect payment from the insurance company covering the office but he instead found himself at the other side of the insurer[=/=]insured relationship.
* ''WesternAnimation/FamilyGuy'': Peter Griffin once got a volcano insurance. After [[ Eyjafjallajökull erupted in 2010]], [[MemeticMutation people started joking]] about how [[HilariousInHindsight he got the last laugh]], or at least would have had he lived in Western Europe.
* The ''WesternAnimation/GravedaleHigh'' episode "Monster on Trial" had Max Schneider try to collect on his insurance after Miss Fresno [[FrivolousLawsuit falsely sued him and student driver Reggie Moonshroud for rear-ending her car]]. He is denied the insurance because the policy doesn't cover werewolves driving his car.

* In his comedy monologue "Ten Days in Coronary Care", Wendy Bagwell described his health insurance as covering "Hong Kong flu. Provided you caught it in Hong Kong. From a Siamese cat."