Impossible Insurance

Alice sells Bob an insurance. Let's say, a life insurance. Looks pretty good; the rates are low, but the payout is high, maybe a million dollars. But when Bob later takes a closer look to the small print, he finds out that his people may only collect the money if he is killed by lightning. In the bathtub. On a Tuesday. [In Utah, on a mountain top, during a rainstorm, while holding a llama...]

That's this trope: An insurance with conditions attached making it almost impossible to collect the money. Bonus points if the impossible becomes possible.

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.

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 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 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.

Live Action TV
"Vicar: It's about this letter you sent me regarding my insurance claim.
 * An episode of 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 Monty Python's Flying Circus, a vicar had bought some insurance and has now come to collect on it.

Devious: Oh, yeah, yeah - well, you see, it's just that we're not...as 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 Morrison...in your policy...in your policy...here 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."


 * The MAD parody of Highway to Heaven used this trope.

Newspaper Comics

 * In The Gambols 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.

Comics

 * In Judge Dredd, 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.
 * Scrooge's interpretation of the insurance policy is exactly how just about every policy involving "fire" is interpreted.

Radio

 * There are a number of examples in The Goon Show, eg:
 * 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 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, 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 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 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, Failure Is the Only Option.

Western Animation

 * 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 Neds 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.