Wills so often reflect not only the wishes of a testator, but their character and sense of humour (good and bad). For some, the temptation to cause mischief or raise a smile from beyond the grave is too much to resist.

Here is my roundup of some of the most bizarre will provisions of all time.

To boldly go

Gene Rodenberry, the creator of Star Trek, loved space and science fiction so much that he requested that his body be cremated and his ashes scattered in space. His famous quote “to boldly go where no man has gone before” was realised when his final wishes were carried out in 1997 when his ashes were shot into the atmosphere as the satellite orbited the planet.

$12m to a dog

In 2004, the notoriously egomaniacal hotelier Leona Helmsley famously left $12 million to her Maltese, Trouble, while entirely cutting two of her grandchildren out of her will (for "reasons which are known to them"). Her other two grandchildren didn't get off the hook entirely; their inheritances were contingent upon their regularly making visits to their father's grave, where they would have to sign a registration book to prove they had shown up. 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.

The “Great Stork Derby”

Charles Vance Miller was a Toronto-based attorney with a love of practical jokes. Charles died in 1926 leaving no descendants or close relations. His last will and testament bequeathed his fortune to any Toronto woman who could produce the most offspring in the decade following his death. The result became known as the “Great Stork Derby.” Four winners emerged in a tie for nine children.

An annual séance

The renowned master escapee and daredevil Harry Houdini died in 1926 on Halloween. Towards the end of his life, Houdini had become mystified by the idea of an afterlife and spiritual mediums. His last will and testament stated that a séance should be held each anniversary of his death. Houdini promised his wife, Bess, that he would contact her in the afterlife, using a pre-planned ten digit secret message that only she would know. For 10 years his wife held a séance on Halloween. Houdini never turned up.

A daily rose

For the ultimate romantic gesture, take note. When the legendary US comedian Jack Benny died in 1974, he left instruction in his will for one long stemmed rose to be delivered to his widow every day for the rest of her life.

A new husband

In dramatic contrast to the above, German poet Heinrich “Henry” Heine used his will to deliver one final insult to his wife, Matilda. Henry left her his entire estate, but only on the condition that she remarry. Perhaps you are thinking that Henry wanted to ensure financial security or companionship for his beloved wife once he was gone. Wrong. Henry made it clear in his will that he made the provision so that “there will be at least one man to regret my death”. Ouch.

The “second best bed”

Perhaps the most famous (or infamous) will provision of all time. Poor Anne Hathaway was publicly snubbed by her husband, William Shakespeare, who left the majority of his estate to his daughter instead. If this were to happen today Ms Hathaway might be well advised to consider making a claim under the Inheritance (Provision for Family and Dependants) Act 1975 (assuming her husband was more generous towards her during his lifetime, that is).

A few words of caution

Humour in a will can be refreshing and touching for the family, especially when it’s clearly a vehicle for showing affection. But using a will as a means of getting “the last laugh” may not only be mean-spirited, but the wording can backfire, produce an unintended or invalid result, and invite claims against the estate. Some gifts are invalid if they or their conditions are contrary to public policy. And a conditional gift will be invalid if the condition is too vague or impossible to perform.

As lawyers, it’s not our job to judge our clients for their wishes - but we do, sometimes, need to dissuade them from incorporating ideas into their wills that are unworkable, invalid, or which don’t meet their legal obligations to dependents.