Heirs behaving badly: Playboy princes and other royal bad boys

King Edward VIII and Mrs Simpson on holiday in Yugoslavia, 1936.
King Edward VIII and Mrs Simpson on holiday in Yugoslavia, 1936 | Public Domain

Not every royal is a paragon of virtue. While there have been plenty of solid, dependable types quietly getting on with the job over the centuries, some royals have used their privileged position to have as much fun and cause as much mayhem as possible. While some of the royals in this list eventually saw the error of their ways and settled down to the serious business of ruling, others stayed bad boys to the end ...

Edward VIII

While finding the job of ‘princing’ (as he dismissively called his royal duties) utterly boring, the future Edward VIII loved the flipside of royal life - the late-night parties, the adoration of almost everyone he came into contact with and the attention of a string of high society women, many of them married. Not that their marital status bothered him in the slightest.

Not everyone was enamoured with the glamorous playboy prince, of course. Principal among them was George V, Edward’s father. The two couldn’t have been more different. Edward was amiable, outgoing and fun; his father was stolid, dependable and dull. While Edward collected ladies, his father collected stamps. George strongly disapproved of his son’s frivolous lifestyle and feared for the future of the monarchy after he was gone. “After I am dead, the boy will ruin himself in twelve months,” George told the British Prime Minister, Stanley Baldwin.

George’s prophecy came true. In 1930, Edward met and fell madly in love with American divorcee Wallis Simpson. When he became king in 1936, the headstrong young monarch was determined to marry Wallis. The British establishment was having none of it and Edward was forced to abdicate in favour of his taciturn brother Albert, who went on to become George VI. Free of the shackles of monarchy, Edward married Wallis in 1937 and the two lived in exile in France after the Second World War as the Duke and Duchess of Windsor until Edward’s death in 1972.

Edward VII

Edward VII spent most of his life living in the shadow of his mother, Queen Victoria. During his decades as a frustrated monarch-in-waiting, Edward devoted his time to his favourite activities - travelling, eating the finest of foods, gambling and women. Nicknamed ‘Dirty Bertie’, Edward kept several mistresses throughout his life and gained an international reputation as a womaniser and playboy. His most famous mistresses included the actress Lilly Langtree, society hostess Daisy Brooke and Alice Keppel, the great grandmother of Camilla Parker Bowles. Edward married Alexandra of Denmark in 1863, though this did little to curb his lusty activities. He continued to travel the world, seeking out the highest stake card games while chasing the ladies - a man with very little to do other than indulge himself while waiting for his mother to die.

Victoria finally obliged him in 1901. Edward was fifty-nine when he ascended the throne. Unfortunately, his years as a celebrated roustabout meant he wouldn’t reign for long. A heavy smoker and overweight, Edward developed breathing difficulties as he got older and eventually had a series of heart attacks. He died in 1910 after just nine years on the throne.

George IV

George IV was once memorably described as a ‘bad son, a bad husband, a bad father, a bad subject, a bad monarch and a bad friend’. The eldest son of the long-lived and much loved George III, George IV was a drunkard, a glutton and a womaniser of the highest order. Pompous, vain and ignorant, the prince was able to indulge his every whim thanks to the generosity of parliament, who granted him larger and larger sums of money to fuel his extravagant lifestyle. George happily accepted the cash thrown his way, spending vast sums on food, booze, women and his personal pet projects, such as the extravagantly unnecessary Brighton Pavilion.

George’s extravagant lifestyle inevitably caught up with him in the end. As a result of his gluttony, the king grew in size until his waist measured fifty inches and he was riddled with gout, so much so that he could not sign documents or walk. In agony from various, mainly self-inflicted ailments, he was drugged up to the eyeballs on laudanum which rendered him mentally incapable in his final years; he was also blind from cataracts. George died in 1830 at the age of 68. “There never was an individual less regretted by his fellow-creatures than this deceased King,” was The Times’ withering response to the king’s death. He would not be missed.

Peter the Great

At the end of the 17th Century, Peter the Great of Russia was on a tour of Europe. The purpose of his tour was to study the scientific and cultural innovations of the west with the intent of modernising his own backward country. What he did more than anything, however, was get right royally hammered at every opportunity.

In the early months of 1698, Peter and his entourage arrived in London and took up residence in a mansion in Deptford owned by the celebrated writer, John Evelyn. Peter and his friends had a rip-roaring time there, getting blind drunk every day, smashing up the furniture and wrecking everything in sight. According to contemporary reports, every chair in the place was used for firewood, all the floors and carpets were destroyed and the house’s picture gallery was used for target practice.

However, the destruction inside the house pales in comparison to what happened to Evelyn’s prized holly hedge. The hedge was nine feet high, five feet thick and four hundred feet long and Evelyn was immensely proud of it. On discovering three wheelbarrows in the grounds, Peter and his drunken companions invented a new game - one of them would climb in a wheelbarrow while another rammed the barrow repeatedly through the hedge at speed. This game proved so popular that by the end of Peter’s visit, the entire hedge was a mangled mess, much to the horror of the house’s owner.

Peter’s modernisation of Russia would eventually earn him the nickname ‘the Great’. While he may have been great to his people, to John Evelyn he was that drunken yobbo who wrecked his house and destroyed his beloved hedge.

Charles II

Charles II was a notorious womaniser, responsible for siring at least a dozen acknowledged illegitimate children (and many more unacknowledged ones, by all accounts). Throughout his life, he kept a large number of mistresses including the famous actress Nell Gwynn and the ancestor of the late Princess Diana, Lady Barbara Villiers. Charles’ legendary randiness earned him the nickname ‘Old Rowley’ after a famous racehorse of the time who was a notably fertile specimen.

While Charles’ rampant libido endeared himself to many of his subjects, not everyone was pleased with their lusty king. Many resented the fact that their tax money was spent on propping up Charles’ mistresses and his many, many illegitimate children. Luckily for this ‘Merrie Monarch’, the thirst for revolution had already been slaked courtesy of a certain Oliver Cromwell, and nobody wanted to go back to the miserable regime he’d imposed on the country. Charles was free to philander his way through polite - and not so polite - society to his heart’s content.

Charles died in 1685 at the age of 58. ‘Other kings had inspired more respect,’ wrote historian Professor Ronald Hutton, ‘but perhaps only Henry VIII had endeared himself to the popular imagination as much as this one. He was the playboy monarch, naughty but nice, the hero of all who prized urbanity, tolerance, good humour, and the pursuit of pleasure above the more earnest, sober, or material virtues.’

Henry V

According to the scholar Tito Livio Frulovisi, the young Prince Henry was ‘a fervent soldier of Venus as well as of Mars; youthlike, he was fired with her torches.’ In other words, Henry was a lusty young pup who enjoyed the company of women as much as he did a drink or ten. The man who would one day become the legendary Henry V was notorious in his youth for carousing and fornicating, so much so that even while spending five years quelling a rebellion in Wales, Frulovisi notes he had plenty of time to find ‘leisure for the excesses common to ungoverned age’. Such was Henry’s reputation for getting drunk and indulging in the pleasures of the flesh, that he was immortalised by none other than William Shakespeare, whose fictionalised version of the prince as a drunken layabout who idles away his time in the company of other drunken layabouts is not far from reality. While there may have been no Sir John Falstaff in real life, there were plenty of people to get drunk with, and that suited the thirsty young prince down to the ground.

While Henry’s young life was spent mostly drunk, hungover or drinking to curb the effects of a hangover, all that dramatically changed when he became king in 1413. Many worried that he would carry on being the drunken lout of his youth, but becoming king transformed Henry in quite unexpected ways. He became a devout Christian, a brilliant military commander and a loyal husband to his French wife, Queen Catherine de Valois. He died suddenly at the age of thirty-five from dysentery in 1422 and is now seen as one of the greatest kings ever to sit on the English throne. Not bad considering he spent a large part of his youth so drunk he could hardly stand up.

Written by:

BP Perry