"And finally, to my Lawyer, who has helped me on this will, I leave not a boot to the head, but a rabid Tasmanian Devil, to be placed in his trousers?!..."A will that contains ridiculous bequests, strange conditions and other weird oddities. This type of will often contains demeaning, cumbersome tasks to earn the fortune and might openly insult the inheritor. The inheritors are usually people you wouldn't expect to receive the inheritance, such as strangers, unknown relatives or even pets. The will may also contain bequests that no one would ever want or need. Sometimes, however, a twist will be used to make the bequeathed gift only look useless at first but turns out to contain something more valuable. While not an everyday thing in the past, it was still not uncommon. Not really seen nowadays, as judges, juries, and probate courts are much less willing to put up with nonsensical bullshit that people try to sneak into their wills. See also On One Condition and Bury Me Not on the Lone Prairie, which often overlap with this.
— The Frantics, Last Will and Temperament
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- In Brewster's Millions (1985), the plot of the movie is the Silly Will condition: Brewster inherits $30 million, 10% of the estate, and he must spend all of it within a month to get the remaining 90%. The hurdle is that he can't acquire assets, donate, or simply throw the money away, and nobody else may know what he's doing. He spends the movie hiring assistants, renting hotels, and baffling his friends who think money drove him insane.
- House on Haunted Hill (1959) is about a millionaire who leaves a fortune to be shared among some stock horror-film victims if they can spend a night in his haunted house and still be alive the next day.
- In Young Frankenstein, the aged Baron Beaufort von Frankenstein leaves instructions that his estate shall be given to his distant great-grandson rather than shared among a cadre of mooching relatives if said great-grandson has become a respected doctor of his own accord. One of the relatives tries to pass this clause off as insanity. The scene was removed from the final film. Said Baron also wanted the will not to be revealed until it'd be 100 from when he was born, meaning Frederick had to meet the terms until then. The other relatives didn't like having to wait until then to either get the estate or learn they wouldn't.
- Isaac Asimov's Black Widowers short story "To the Barest". When Ralph Ottur (the founder of the Black Widowers club) dies, he leaves a will which requires the members to solve a riddle in order for one of the members to receive a bequest.
- In another, the members have to help a friend who's eccentric uncle required him to solve a riddle in order to receive an inheritence. To raise the stakes, if the riddle wasn't solved, the money would go to the American Nazi Party.
- Subversion: Dumbledore's will in Harry Potter and the Deathly Hallows seems to be this at first, but each item proves to be very significant later.
- In Time Enough for Love, Lazarus Long tries to put together his will so that all his assets will be left to Prostitutes, Panhandlers, and other undesirables beginning with 'P'. When someone points out that probably won't survive legal arbitration, he decides to leave it to a cat shelter instead.
- Though, he has a fairly good reason for the sillyness, it's to keep his assets out of the hands of his less scrupulous relatives in the case that his preferred heir is unable to inherit for some reason.
- In The Ultimate Gift, when his rich granddad, Howard "Red" Stevens, died, Jason thought he was going to inherit a piece of the old man's multi-billion dollar estate, but it came with a condition. In order to get his share of the willed inheritance, Jason must complete 12 separate assignments within a year.
- Unseen Academicals: One of the bequests requires that the wizards engage in hunting the Megapode: carried by University porters, they chase a man with a big bird-shaped hat. The one that sets off the plot, however, requires that the wizards play football (they're not required to win, but try getting Archchancellor Ridcully to understand that).
- In Making Money, Topsy Lavish has an apparently Silly Will that is actually a very clever way of keeping the bank out of the hands of her greedy, incompetent and in one case actually insane family. She leaves her dog Mr. Fusspot to Moist von Lipwig, and leaves fifty percent of the shares in the bank to Mr. Fusspot, who already owned one, thereby making him the Chairman and Moist his "interpreter." Additionally, a contract is lodged with the Assassins' Guild to kill Moist if he fails to take care of Mr. Fusspot, meaning nobody else can have Moist Assassinated—and the Assassins' Guild would never accept a contract to kill a pet.
- In the Lord Peter Wimsey story "The Piscatorial Farce of the Stolen Stomach", a wealthy man leaves his stomach to his great-nephew, a medical student. When Lord Peter decides he wants to see the actual wording of the will, he poses as an author collecting examples of comic wills.
- Actually a Secret Test of Character of sorts. Just before his death, the uncle had purchased a set of twelve matching diamonds worth millions, then swallowed them and jumped out a window. Since the will specified that the great-nephew in question inherited not only the stomach but all contents therein, he could collect the fortune by discovering the diamonds' hiding place.
- Another Wimsey story has the eccentric uncle leave his fortune to the (Conservative) Primrose League, just to annoy his Communist niece. There's a covering note, explaining that there's a later will leaving the money to her, if she can be frivolous enough to find it.
- The Hercule Poirot short story "The Case of the Missing Will" has an eccentric old man write a will which gives his neice a month to "prove her wits", after which the estate goes to charity. She interpretes this, correctly, as meaning she has to find a second will dated after this one in which she's the beneficiary.
- A similar Miss Marple story has a young couple tearing an inherited Big Fancy House looking for an uncle's inheritance (the garden looks like a war zone, and since it's already dug up they're considering planting vegetables). Miss Marple ends up putting them on the right track by showing them the secret drawer in an old desk, which a younger expert hadn't found. They find a bunch of love letters and recipes, which depresses the couple to no end... until Miss Marple, who is reminded of her own uncle with less-than-amusing trickster tendencies, tells them to look at the (extremely rare and valuable) stamps on the letters.
Live Action TV
- In The Legacy of Reginald Perrin, Perrin leaves a fortune to be shared among his friends, on the condition that they each do something sufficiently absurd.
- Slings and Arrows has Oliver, who asked to have his head severed upon his death so it can be stripped of flesh and used in a production of Hamlet.
- On Titus, when Christopher Titus' mother committed suicide, one of the apparently many oddities in her will, was for Christopher to eat Apples. The catch? Apples was her mother's pet dog when she was little. The lawyer then gives him a frozen (enveloped in silver foil) dog corpse.
- On The IT Crowd, a Video Will contained a long sequence of the deceased eating an apple for no apparent reason. It also contained some incriminating evidence about accounting irregularities.
- Back when the title character of My Name Is Earl was still married to Joy, Earl's will consisted of a very brief recording (made on a stolen video camera, taped over a home movie of an elderly woman's birthday party) of Earl drunkenly stating how much he loved Joy and that everything he owned would be hers if anything happened to him, before the couple proceeded to have drunk sex on The Couch. This causes problems for him later, seeing as she tries to kill him in order to get the lottery money he won and claimed after she divorced him for Darnell. Earl gets a real, legitimate, sober will drawn up while Joy waits for a background check on a handgun, ensuring that even if she did kill him, she would get nothing.
- In Community:
- Pierce's father's will stipulates that whoever kills him will receive his ridiculous ivory toupee. Because Jeff was shouting at him when he had his fatal heart attack, it goes to him. He also gives Pierce's inheritance to him On One Condition: that he win a video game competing against seven of his closest friends, because Pierce once annoyed him by suggesting that he invest in the video games industry.
- Pierce himself also inserts On One Condition into his will twice. Firsty, his must friends all answer a series of questions while hooked up to lie detectors. This is ostensibly to determine if they played any part in his death, but is mostly an excuse to mess with them one last time. Secondly, Troy must sail around the world in Pierce's yacht to receive the bulk of his fortune. He also gives them all a container of his sperm. This makes a tiny bit of sense for the first person, but less and less until the end when it's listed as "obligatory sperm."
- In WKRP in Cincinnati, a millionaire leaves a Video Will to tell his relatives he's leaving them absolutely nothing. (And also tell them exactly how he feels about them.) He also leaves Jennifer (who he had been dating, and said relatives had accused of being a Gold Digger) exactly one dollar, the special first dollar he ever made, along with instructions on what to do with the rest of his belongings, which she starts to arrange later.
- On The Golden Girls, Rose mentions her late husband Charlie set up a gag will that left everything to the family's cow. Unfortunately, some lawyer managed to get a hold of the will and tried to make sure the cow got everything. Rose explains she had to testify in front of what is implied to be a jury of farm animals. Thankfully, Rose won the case, and celebrated... with a steak dinner.
- One episode of The Burkiss Way featured the reading of the will of a Lord Hackingbottmo. The will begins with a long list of people who have been left nothing, in increasingly elaborate language ("...nil pennies; the zero sum..."). This is followed by a list of people who have been left vaguely described but clearly unpleasant things ("...a rather nasty substance...something not nice in any way shape or form—and a four year supply of refills..."). An attempt to find someone who has been left something nice then turns the reading into a performance of "Chattanooga Choo-choo." This is disrupted by someone finally pointing out that Lord Hackingbottmo is the person reading the will out in the first place.
- The provider of the page quote is "Last Will and Temperment" (better known as Boot to the Head) by The Frantics. The routine plays with the trope quite well, and can best be appreciated by listening for yourself.
- Futurama episode "The Honking" begins when Bender is left a haunted castle, belonging to his uncle Vladimir, on the condition that he spend one night in it. The will also contains the clause 'To my loyal butler, You There, for his decades of service, I leave a pittance, to be paid in 20 equal installments of one-twentieth of a pittance each.'
- In The Boondocks, Granddad's old war frenemy leaves him an unspecified "something good" in his (video) will in return for Granddad delivering a kind and respectful eulogy, which he knows Granddad will hate. The inheritance turns out to be deez nuts, nyiggah!
- The Simpsons: "Bart the Fink" begins with the Simpsons at the reading of their late aunt Hortenses' will, which stipulates they will receive one hundred dollars each on the proviso they spend a night in a haunted house. When Marge questions this, the executor just replies it's a standard clause. The rest of their aunt's money is sent to Anne Landers.
- Charles Vance Millar, Canadian lawyer who had made a lot of money from his legal practice and even more money from some good investments (e.g. investing in the Detroit–Windsor Tunnel) who, when he died, had no close relatives to give it to. He therefore determined to write as silly a will as he could imagine (and pass muster in probate). His will included things such as:
- Giving three lawyers known to despise each other lifetime joint tenancy together in his vacation house in Jamaica. Note that joint tenancy is a form of ownership giving the "tenants"—owners, really—equal rights to it, and grants the last of the tenants to die a right of survivorship: i.e. the survivor takes the property outright (creating a perfect situation for a Tontine). But Millar had provided for that, as well: the house was to be sold at the end of the survivor's life and the proceeds to be distributed to Toronto's poor. (Fortunately for the lawyers in question, the house had been sold off some time previously, meaning that they couldn't get the house or anything else from Millar's estate.)
- Giving two known opponents of horse racing $25,000 worth of Ontario Jockey Club stock. (He also gave shares to someone too shady for the Club's tastes.)
- Giving every practicing minister in three towns a share in another nearby jockey club...which shares turned out to only be worth half a cent each, but only after the ministers had all publicly agonised about the bequest.
- Giving a group of prominent Protestant prohibitionists $700,000 worth of shares in a Catholic brewery—on condition that they participate in the brewery's management and draw on its stock dividends. (Fortunately for the prohibitionists, he had also sold the stock shortly before his death.)
- Saying that the remainder of his (quite considerable) estate was to be converted to cash 10 years after his death and given to the woman in Toronto who gave birth to the most children in that time. This became known as the "Great Stork Race". This was generally seen as his protest against people who criticized the childless and encouraged childbearing.
- Ingrid Newkirk (as in, the head of PETA) has a will that is... disturbing. According to her will (viewable online on the PETA website) she wants to donate her body to "alleviate animal suffering". Specifically, she wants her flesh (or at least part of it) to be barbecued, her skin turned into handbags, her lower legs turned into umbrella stands, her eyes sent to the Environmental Protection Agency, and her hands sent to the owners of Ringling Brothers Barnum and Bailey Circus. (Did we mention that most of PETA's detractors call Newkirk batshit insane?)