Leaving instructions for what should happen to your finances after your death is a serious matter – but for some, the temptation to cause mischief or raise a smile from beyond the grave is too much to resist:-

1) A daily rose – Legendary US comedian Jack Benny left an unusual but touching instruction in his will when he died in 1974. “Every day since Jack has gone the florist has delivered one long-stemmed red rose to my home,” his widow Mary Livingstone wrote in a magazine, shortly after his death. “I learned Jack actually had included a provision for the flowers in his will. One red rose to be delivered to me every day for the rest of my life.”

2) Anonymous donation –  “to clear the national debt” A public-spirited donor made a half-million-pound bequest to Britain back in 1928, which is now worth more than £350m. Unfortunately, the anonymous donor was very specific about how the money should be spent: it should only be passed on once it is enough to clear the entire national debt. Sadly, the total national debt currently stands at £1.5tn and so the country can’t touch the money.

3) A boozy weekend – We all like to think that our friends will raise a glass to us when we’ve gone, but Roger Brown made sure of it. The 67-year-old lost his life to prostate cancer in 2013, leaving behind a secret bequest of £3,500 to seven of his closest friends, with the proviso that they use it for a boozy weekend away to a European city.

“We would like to formally apologise to Roger’s two sons, Sam and Jack, for taking away some of their inheritance,” beneficiary Roger Rees told the South Wales Evening Post after the friends spent a weekend in Berlin. “We spent most of it on beer, the rest we wasted.”

4) The “second-best bed” Poor Anne Hathaway, aka Mrs Shakespeare, has gone down in history as being snubbed by the Bard from beyond the grave. In his will, Shakespeare left her his “second-best bed” while the vast bulk of his estate went to his daughter Susanna.

5) $12m to a dog In 2004, billionaire hotelier Leona Helmsley left instructions for her $4bn (£2.5bn) fortune to be spent caring for dogs, having apparently re-thought an earlier draft that left it to the poor. Her nine-year-old Maltese, Trouble, received $12m (£8m) in the will, with her grandchildren either cut out or ordered to visit their father’s grave annually in order to inherit their share.

Trouble’s inheritance was later cut to just $2m (£1.2m) by a judge, although the dog still needed to go into hiding amid death and kidnap threats.

6) Flowers for Sidmouth – When self-made millionaire financier Keith Owen, 69, was diagnosed with cancer and given just a few weeks to live, he decided to donate his entire £2.3m fortune to his favourite holiday spot, Sidmouth in Devon.

The money was given to the Sid Vale Association, with the stipulation that some of it was to be spent on one million flowering bulbs to keep the coastal town awash with colour. His will specifies that the capital should not be touched, but that the interest – about £125,000 a year – be spent on maintaining the town and two nearby villages.

The town has not yet planted the million bulbs, saying this could take a few more years.

7) A new husband for some embittered spouses a last will and testament is actually the last chance to insult their life partner one more time. So, it was for German poet Heinrich “Henry” Heine who left his estate to his wife, Matilda, in 1856 on the condition that she remarry, so that “there will be at least one man to regret my death”. Ouch.

8) A legacy of bitterness Michigan, USA millionaire Wellington Burt used his will to put his enormous wealth out of reach of his family for almost a full century. When he died in 1919, his will was discovered to specify that his vast fortune would not be passed on until 21 years after the death of his last surviving grandchild. She died in 1989 and the 21-year countdown ended on November 2010. About 12 people discovered they were beneficiaries of the strange will, described as a “legacy of bitterness”, and they shared a fortune estimated to be worth $110m.

9) A wife for a gay son – When Frank Mandelbaum’s will was read in 2007, it was discovered that he had left behind a $180,000 trust fund for his grandchildren. There was one additional clause, though, which concerned his son Robert. Robert’s children would only inherit a share if Robert agreed to marry their mother within six months of their birth.

One small problem: Robert is gay and is raising his son, Cooper, with his husband.

10) Seventy strangers from a phone directory It’s the stuff of daydreams and film scripts. When Portuguese aristocrat Luis Carlos de Noronha Cabral da Camara wrote up his will, he left his considerable fortune to 70 strangers randomly chosen out of a Lisbon phone directory. “I thought it was some kind of cruel joke,” a 70-year-old heiress told Portugal’s Sol newspaper. “I’d never heard of the man.”

Will power

If you absolutely insist on a joke or an odd request, check to see whether this could invalidate the will and avoid doing it if it could. For more outlandish requests, it may be better to use the non-legally binding letter of wishes.