The Ugliest Royal Portraits of All Time

This preposterous boy-man portrait of Charles II of Spain

Charles II of Spain was born November 6, 1661, and became king in 1665 at the tender young age of four. His mother ruled as a regent for 10 years until Charles was a teenager. While it sounds like this guy really had it made from a young age, unfortunately, he had one big problem: He had a face even a mother could not love. The Habsburgs were so bent on keeping power, as they had for a few hundred years, that they often married their own blood relatives. After 16 generations of this, Charles II’s family was so inbred that his grandmother and his aunt were the same person. So here we have it: the Habsburg Jaw curse. Actually, this was such a prominent family trait and curse, that a whole team of scientists decided to explore the genetics behind it.

It is almost universally known that one of the most important roles of a royal marriage is producing heirs. This responsibility that monarchs must undertake determines a great portion of their lives. But unfortunately for the Habsburgs, the genetics were not in favor of Charles II when he was born. He was impotent and could not father children. It was part of his family’s legacy of inbreeding. He probably suffered from two genetic disorders. First, there was combined pituitary hormone deficiency, a disorder that made him short, impotent, infertile, weak, and have a host of digestive problems. The other disorder was distal renal tubular acidosis, a condition marked by blood in the urine, weak muscles, and having an abnormally large head compared to the rest of the body.

The Mole Man? Ferdinand II of Spain by Michel Sittow

Not to be confused with the Holy Roman Emperor Ferdinand II, Ferdinand II of Spain had one heck of a royal portrait. Ferdinand II was the King of Sicily, Aragon, Castile, Naples and Navarre. Here, we have a prime example of the trademark Habsburg Jaw. As you can see here, that means that there was a very weak chin and soft jaw… but not flattering at all. Having the Habsburg Jaw is oftentimes used as an offhanded insult. As a devout Catholic, he would have not partaken heavily in spirits. However, there is something definitely wrong with his eyes that would make one thing he’d been either heavily influenced or dog tired.`

The early part of his reign was characterized by brutal fighting and forced conversions in Moor-held Spain. He was ruthlessly effective though, bringing to a close the several-century long period known as the Reconquista. Ferdinand is most famous for patronizing the Age of Discovery. It was he and his wife Isabella I who funded the expeditions of Christopher Columbus. The painter, Michel Sittow, was a very popular and respected portraitist of the time. So it’s strange that this particular portrait stands out in such a negative way. We don’t know when this unflattering portrait was made, but considering he died in 1516 aged 63 we can reasonably guess it was sometime during this time in the late fifteenth century.

This Grotesque ‘Likeness’ of King Henry VIII

We all know that Henry VIII was known for his bad habit of exterminating wives. Of course, he was the King of England, but based on this portrait, it’s a shock that he was able to have any brides at all. Universally known, Henry VIII’s portrait by Hans Holbein the Younger is perhaps the iconic image of monarchical power. It’s the typical portrait you see of Henry VIII, which has been dated to the 1530s. It depicts Henry in an almost frontal pose similar to one used by Holbein in various other portraits. The head, with its distant gaze, has an almost architectural solidity. The picture of kingly regality. An image that is almost like propaganda to any viewer. That is not what the above portrait aims to represent.

Cornelis Massys’s unflattering portrait represents a very different Henry VIII. The disfigured-looking Henry VIII looks rather villain-like and grotesque. It was later engraved by Peter Isselburg, however, there were no consequences from the monarch. Because he never actually saw it. The infamous King met his end the year before it was completed. We know that towards the middle and end of his life, Henry VIII had suffered a leg injury. The injury had its beginnings during his first jousting accident in 1527, however, his physical fate was sealed when he suffered a more serious injury in 1536 during another jousting incident. Henry suffered a severe concussion and burst a varicose ulcer on his left leg. His injuries and lifestyle catapulted him into his abysmal reputation. These ulcers never truly healed and Henry had constant, severe infections as a result.

Henry VIII – Ugly Portraits, Ugly Personality, Ugly End

At this point in his life, Henry VIII was not pleasant to be around. The jousting accident, which had prevented him from enjoying his favorite pastime, had also prohibited Henry from exercising. Henry’s final suit of armor in 1544, three years before his demise, suggests he weighed at least three hundred pounds. By 1546, Henry had become so large that he required wooden chairs to carry him around and hoists to lift him. He needed to be lifted onto his horse and his leg continued to deteriorate. It is this image, of a morbidly obese king, that most people recall when asked about Henry VIII. Henry’s later years were a far cry from the valiant, charismatic prince of 1509.

The endless pain was undoubtedly a factor in Henry’s metamorphosis into a bad-tempered, unpredictable and irascible monarch. Persistent chronic pain can severely impact quality of life – even today- and with the absence of modern medicine, Henry must have been faced with excruciating pain daily, which must have had an impact on his temperament. Henry himself wrote to the Duke of Norfolk, excusing himself from traveling and confessing: “to be frank with you, which you must keep to yourself, a humor has fallen into our legs and our physicians advise us not to go far in the heat of the day”. He would have likely been suffering from sepsis and fevers. Soon after, Castillon to Montmorency from the English Court, wrote: “and for ten to twelve days the humours which had no outlet were like to have stifled him, so that he was some time without speaking, black in the face and in great danger.” It paints an uglier picture even than the portrait by Peter Isselburg. This was a cycle for Henry VIII until he succumbed to his ailments in 1547.

The Glamorous Leopold I by Benjamin Block

Leopold I was yet another interesting face courtesy of the Habsburg Dynasty. Of course, this particular royal was far more glamorous than the other Habsburg we’ve seen in this list. He was the “glamor boy” of the Holy Roman Empire. His entire rule was defined by two things: tirelessly campaigning against the Ottomans and French and looking absolutely fabulous while doing it. But that doesn’t mean that his portraits weren’t a train wreck. Leopold I was a member of the Habsburg Dynasty. Despite his imperial legacy—and the rather loud armour he’s donning in the portrait—he shied away from military life, dedicating his time to music, hunting, riding, and ruling as an absolute monarch.

The artist, Benjamin Block, came from a family of painters. Both his brothers were painters, as was his father Daniel. (Some might have described him as a chip off the old Block). He was “blessed” with that defining family feature: the Habsburg Jaw. And it was a prominent jaw at that. For his iconic look and status, a coin type was minted in 1670 after his likeness… which displayed his jaw to comedic effect. Due to this, he earned the nickname, “The Hogmouth.” But what is it about the Habsburg Jaw? Why does it keep coming up? More than likely this is due to inbreeding within the royal lines. But this was not the only unfortunate gene the Habsburgs could inherit. The family was also riddled with epilepsy, gout, depression and dropsy. Other royals in the Habsburg family were so hindered by the Habsburg Jaw that they even had trouble eating.

We couldn’t leave this little number out

Leopold commissioned Jan Thomas to do these portraits of him and his wife, Margaret Theresa, for the occasion of their marriage in 1666. And these weren’t even the weirdest portraits Jan Thomas produced during his long and illustrious career. Leopold was a very educated monarch. From an early age, he combined his deep learning in history, languages, the natural sciences and music with a devout sense of duty to his empire. But he was also rather insecure, eager to use any public occasion to enhance both his own personal prestige and the prestige of Vienna as a worthy imperial residence. He would often hold theatrical productions at the palace in which both he and his wife would take part themselves.

As well as a few productions the emperor had written himself, Italian ballets and operas were given priority as these were considered the most sophisticated. And it’s in the role of the character of one of these—Acis from “La Galatea“—that the Holy Roman Emperor is posing in the portrait above. A Turkish traveler once described Leopold as “a cultivated man of extreme ugliness”. It’s not hard to see why a Turk might have taken that view. Leopold was actually a phenomenally successful monarch, transforming Austria into a European power by the end of his reign. Believe it or not, Leopold was clearly very pleased with Thomas’s portrait because he kept him on at the imperial court. Up until 1960, the portrait’s whereabouts was pretty much unknown as it belonged to the part of a private collection.

King Ferdinand VII of the Caterpillar Eyebrows

The reign of Ferdinand VII (1784-1833) was one of the most complex and important in the history of Spain. In fact, he was known for not being the King of Spain once, but twice in his life. His rule was characterized by a popular dispute against French occupation and by the struggle of liberal groups to establish a constitutional monarchy. This royal fella was no friend of the media. Additionally, under his rule, Spain lost nearly all of its American possessions, and between 1808 and 1813, during the Napoleon’s era, Ferdinand was imprisoned in France by Napoleon. This guy had an extremely eventful life. So we’re just listing a few key moments in his history. In addition to everything else, he suppressed the liberal press from 1814 to 1833, jailing many of its editors and writers.

One of his most contested moves was the Pragmatic Sanction of King Ferdinand VII, (March 29, 1830). The Pragmatic Sanction was intended to permit his unborn child to succeed to the throne, even if it were female. This promulgated his predecessor Charles IV’s unpublished decision of 1789 revoking the Salic law of succession, which had denied royal succession to females. Ferdinand, still childless at the passing of his third wife, María Josefa Amalia, in 1829, married María Cristina I of the Two Sicilies. This threatened the mounting hopes of his brother Don Carlos regarding the succession. The birth of a daughter, Isabella, in October 1830 greatly complicated the issue. By the ancient law of Castile and Leon women could rule in their own right. This right had, however, been abrogated by an act of 1713 designed to prevent any union of the crowns of Spain and France. The country entered into large-scale civil unrest upon his passing. His political legacy has remained contested since his passing, with some historians regarding him as incompetent, despotic, and short-sighted.

The Play Soldier, King Philip IV of Spain by Gaspar de Crayer

Wow, Spain has a lot of these horrific portraits. King Philip IV of Spain dressed up as cuirassier and stood for a number of modeling sessions with Gaspar de Crayer. Ruling for an astounding 44 years, Philip’s personality is often regarded as reflecting the decline of Spain as a Great Power. Spain’s greatest enemy during this time was France, which entered the Thirty Years’ Conflict in 1635. The reason for this was the successes of the imperial army in the Empire, which received diplomatic and financial support from Spain, against the Protestant electors. France entered into an alliance with Sweden, Holland and Savoy, declaring their intentions against Spain to relieve its allies in the Empire. The Habsburgs were thus caught in a conflict on two fronts, and their initial successes turned into defeat: the dynasty was made painfully aware of the limits of Habsburg fantasies of omnipotence.

Funny enough, after achieving this portrait, Philip needed more. Philip demanded that Gaspar de Crayer painstakingly paint the same portrait again. Only this time with his court dwarf standing by his side. Whether to draw attention to his height or because the dwarf was a favorite of Philip we’ll never know. We can only hope this wasn’t meant to be serious, and that Philip wasn’t in fact so insecure that he had to stand beside an actual dwarf to feel suitably regal. It’s possible he did. On the throne from 1621 – 1665, Philip IV presided over Spain during its slow decline as a world power. Philip’s Spanish Empire had just cut itself loose from the costly Thirty Years. Additionally, Philip did not have very strong reproduction skills either, the sons that were born to him had weak constitutions and there were doubts as to whether they would survive.

Mary, Queen of Scots and her Creepy Little Man-Child

Could nobody depict King James I and VI like a normal child? This portrait invokes a fit of laughter at the absurdity of it. This is yet another portrait that could be perfect art history meme material. But it seems like painters in the 16th century spent very little time with children, therefore did not know how to paint their likeness at all. Of course, Mary, Queen of Scots was quite a tragic figure. So you can only giggle so much at this painting. The royal succession feud between Mary and Queen Elizabeth I of England is probably one of the most documented royal feuds of all time. Books, movies, and shows have romanticized and sensationalized the life of Mary, Queen of Scots.

Relations between Mary and Elizabeth had soured following the Scottish queen’s union with Darnley (aka Henry Stuart), which the English queen viewed as a threat to her throne. But by February 1567, tensions had thawed enough for Mary to name Elizabeth “protector” of her infant son, the future James VI of Scotland and I of England. But after the news broke of Darnley’s demise, things began to escalate once more. Mary was caught up in the scandal of her husband’s untimely end and then married his accused perpetrator, James Hepburn, Earl of Bothwell. This made Mary increasingly unpopular amongst her people. In summary, she was imprisoned and forced to abdicate her crown to her son. She escaped and fled to England, believing that Elizabeth would offer her sanctuary and support. And she did, in a way… Elizabeth placed Mary—an anointed monarch over whom she had no real jurisdiction—under de facto house arrest, consigning her to 18 years of imprisonment under what can only be described as legally grey circumstances.

Related:

• The Seedy Plots That Overthrew Mary Queen of Scots
• Major History Mistakes Made in the Movie Mary, Queen of Scots

Queen Elizabeth I Inspired a lot of Ugly Portraits

Daughter of King Henry VIII and Anne Boleyn, Queen Elizabeth I is arguably one of the most famous and influential monarchs this world has ever seen. Such power and influence inspired many artists to capture her spirit in a portrait. But some of them did not capture her in the best light… this portrait above does not have an artist attributed to it. But it’s obvious that not only did Elizabeth I see better days than in this painting – the painting itself has seen better days. Some of the paint is missing, which contributes to the morbid discoloration you see on her. While we may not know if this is an accurate representation of Elizabeth I, it is interesting to dive into what she may have looked like towards the end of her life. Even though her power and fame are near-immortal status, she still was a human at the end of the day.

By the end, Elizabeth was in pretty rough shape. The 69-year-old queen, who had reigned for 45 years, was weak and aged. Her teeth were rotten. The white makeup, which Royal Museums Greenwich maintains was an inch thick on her face, according to some accounts, may have contained enough lead to poison her. It seems she may have worn this due to contracting smallpox around 1562. Smallpox was known to significantly scar its victims. This paints a picture actually fairly similar to what we see in the anonymous portrait above.

Creepy Little Boy Turned Witch Hunter, King James I of England (James VI of Scotland)

With a royal portrait like this early in life, it’s no wonder King James I of England turned into a woman-hater- I mean witch hunter. That’s right. King James I did not just command the country with politics. He also controlled the masses in one of the most infamous witch hunts in history. King James I of England And VI of Scotland is primarily known for uniting the two crowns. But James’ royal obsession with black magic started Europe’s most brutal witch hunts. In the 1590s, King James VI of Scotland’s fear of witchcraft began stirring up national panics, resulting in the torture and end of thousands of lives. According to History Collection writer and historian, Natasha Sheldon, “Scotland was one of the most active areas to persecute witchcraft between the fifteenth and eighteenth centuries. Over this period, it is estimated that around 4,000 people were burnt at the stake. However, the most ardent persecutions occurred during the late sixteenth and early seventeenth century. During this period, any witchcraft- whether it was of good or evil intent became unacceptable. A witch was a witch; bound by a pact to act as an agent of the devil – even if they were using their magic to heal rather than harm.”

In 1597, King James VI of Scotland published a compendium on witchcraft lore called Daemonologie. It was also published in England in 1603 when James acceded to the English throne. The main focus of historians when interpreting Daemonologie has — rightly — been on its attitude towards (and justification of) persecution of witches, which James explicitly endorses not just as justified but as an obligation of all good Christians and rulers. One analysis sums up what Daemonologie truly was: “Although modern readers may assume that any work which focuses on witches, demons, and evil spirits must be of little intellectual value, two things have to be understood. Firstly, that discussions of demons were viewed as a part of legitimate scientific discussion at the time, as God acted through nature and as such spirits could use the natural world as a vehicle for machinations good or evil. Secondly, that Daemonologie is as much a political treatise as a religious/theological one.”

You May Interested: 10 Greek and Roman Trials for Magic and Witchcraft.

Another famous Elizabeth, Another Ugly Portrait

Few women in the world have been depicted as often as the current Queen of England, Elizabeth II. And unfortunately, she hasn’t fared particularly well in the ugly portrait department either. In 2000, the long-reigning monarch agreed to be painted by the late Lucian Freud, a British painter who throughout his career has earned wide respect both at home and abroad. This particular painter is extremely talented – that is worth noting here. So, in reality, the painting itself is not that bad. But something about the lighting and the fact that it took over a year and a half to produce this 9″ by 6″ portrait doesn’t sit right with us. While this masterful painter should not be discredited, this was not a flattering portrait of Elizabeth II. She sat for this portrait on various occasions between May 2000 and December 2001.

It’s worth stressing here that just because it’s unflattering doesn’t necessarily make it a terrible portrait. Lucian Freud is ranked among Britain’s finest figurative painters. It might not be flattering, but it certainly captures the weariness that must come with the amount of experience Elizabeth has had during her decades in office. Praise was forthcoming from The Times‘ art critic Richard Cork, who described the finished piece as, “painful, brave, honest, stoical and above all clear-sighted.” The Sun and its traditionally monarchical readership gave it an ice-cold reception, however; its Royal Photographer, Arthur Edwards, calling for pitchforks at dawn in writing, “Freud should be locked in the Tower for this.” Having said that, The Sun is mainly famous for its topless “Page Three Girls”, so let’s hold judgment on what they have to say shall we.

A Strange Little Man (aka King Frederik VII of Denmark)

Frederick VII (Frederik Carl Christian; 6 October 1808 – 15 November 1863) was King of Denmark from 1848 to 1863. He was the last Danish monarch of the older Royal branch of the House of Oldenburg and the last king of Denmark to rule as an absolute monarch. But… that doesn’t mean he was that dedicated to ruling. As a Crown Prince, Frederik lived a debauched life, which contributed to the discussions concerning the abolishment of the absolute monarchy. The year after his succession Denmark became a constitutional monarchy with the King’s signing of the Constitution on the 5th June 1849. His reign was marked by the national confrontation in Schleswig-Holstein, at which the King became a national symbol of unity.

Frederik VII was unstable by nature, but his unpretentious style won him many supporters. His marriage to Louise Rasmussen was the cause of great opposition in bourgeois circles, but the couple were popular with the rural population. However, it seems that the marriage would not have been terribly worth the drama. They were reported to have a very unhappy marriage. This would not be a majorly concerning issue if it were not for the fact that they also were unable to conceive a child – which royals are nuts about. Frederik’s drinking habits and affairs led to unrest in the relationship, ultimately resulting in divorce in 1837. He was the last Danish monarch of the older Royal branch of the House of Oldenburg and also the last king of Denmark to rule as an absolute monarch. During his reign, he signed a constitution that established a Danish parliament and made the country a constitutional monarchy.

Prince Philip, Duke of Edinburgh, by Stuart Pearson Wright

Through the years, Prince Philip, Duke of Edinburgh has not been the most… liked monarch. It could be argued that the royals of today are under more scrutiny than ever due to the debated necessity of their roles entirely. They’re basically symbolic figureheads at this point. But they also have a harder time winning public opinion due to social media, news media, and television. His character depiction in The Crown was not particularly flattering. Pairing those factors along with the circulating rumors of his involvement in particularly unsavory crimes – it’s no wonder he was bound to rack up a bad portrait. In 2004 Stuart Pearson Wright was given the green light by Prince Philip, the Duke of Edinburgh, to do his royal portrait. The Duke declined an invitation to model at the artist’s studio, an old sausage factory in east London. Instead, he insisted that Stuart came to Buckingham palace for four one-hour sessions.

The title of the resulting work is Homo sapiens, Lepidium sativum and Calliphora vomitoria, which is essentially a pretentious Latin translation of “a wise man, some cress, and a bluebottle”. It does exactly what it says on the tin. The bluebottle might seem completely random, and to a large extent it is. But it does derive from the Vanitas tradition in art, which interpolates a worm-eaten apple or falling rose or something similar to tie us to nature and remind us that all flesh is grass. The cress, according to the artist, is a reference to the Prince as seed-bearer to the royal family (good luck trying to get that image out of your head). And then there’s the chest hair. No, it’s not Philip’s torso. It belongs to an anonymous, elderly gentleman who lives in London’s Bethnal Green. Apparently, he was rather startled that his chest had ended up superimposed on the Duke of Edinburgh, but also quite flattered.

Queen Caroline Looking like a Disturbing Mother Goose Character

Queen Caroline was actually a rather odd bird. She was known as unattractive and tactless during her life. According to accounts, she also rarely changed her undergarments… so add stinky to the list of unattractive attributes to Queen Caroline. It was due to her wealth that George IV, Prince of Wales, decided to settle down with her. He had accumulated a steep debt and so turned to marriage to solve his issues. Specifically, marriage to a rich woman. George, also known as “Prinny” settled his sights on the undesirable Caroline. On their wedding night, he was so drunk that he collapsed into the bedroom grate and remained there until dawn. Nevertheless, their only child Princess Charlotte was conceived, so he obviously managed to do what was required of him by his country.

Prinny found Caroline so disgusting that he refused to live with her and a year after their wedding he sent her a note tactfully informing her that she could do as she liked, as he would not be having ‘relations’ with her again. Caroline took this to mean that she could do as she wished. Rejected by her husband she went to live at Blackheath, London where her behavior became more than a little extreme. In her room, she had a clockwork Chinese figure that performed for… pleasure when wound-up. She also was given to dancing around in front of her guests in a manner that was most indelicate, exposing most of her body. Obviously, not a desirable quality for a lady and wife to the Prince of Wales. After many more crazy stories in her life, when George IV was coronated, she was barred from the Abbey… After proclaiming she was “The Queen…Open” and the pages opened the door. “I am the Queen of England,” she shouted and an official roared at the pages “Do your duty… shut the door” and the door was slammed in her face. Unfortunately, the undignified lady demanded a coronation for herself the next Monday. Which was not granted. And she met her end 19 days later.

This Trippy Collage of the Danish Royal Family

In 2013, the first portrait of the Danish Royal Family in 125 years was unveiled. But nobody expected this slightly disturbing painting. Critics went back and forth, saying it looked like a mix between a horror film advertisement and a botched Photoshop attempt. Disappointing news for the artist, Thomas Kluge, who spent four years painting Queen Margrethe and her family. But this honestly doesn’t even look like a painting. The portrait evoked an earlier piece; the last portrait of the Danish Royal Family, set in the hall of Fredensborg Palace in the mid-nineteenth century. But despite the stylistic similarities between the two—not least their realism/hyper-realism—the artist never intended for it. “I was trying to take out realistic depictions because we live in a democratic world and I think our Queen and her family are now symbolic,” Kluge explained. “This is satire.”

Well, at least we can all agree there’s little realistic about the setting. The family float in purgatorial darkness before a crumbling, century-old backdrop of the former palace. It’s the stuff of nightmares, particularly with Princess Isabella (far left) clutching a doll and doing her best demon face. At least the sittings were more fun-filled with the artist playing football with Prince Christian between sessions. Still, at least the Danish Royal Family isn’t as picky as the British. Queen Margrethe at least accepted the work (though without publically commenting as to whether she liked it or not). And Margrethe knows a thing or two about art. As well as being a full-time monarch, she’s a part-time painter: the illustrator for the Danish edition of JRR Tolkein’s “Lord of the Rings” series and a painter in her own right, with a recent exhibition in Denmark’s Museum of National Art.

Where do we find this stuff? Here are our sources:

Husburgers – Phillip IV: Spain’s Late Glory or a Slow Decline?

Wikipedia – James II of Scotland

Wikipedia – The Crown (TV series)

Wikipedia – Ferdinand VII of Spain

James VI & I – Daemonologie

Historic Royal Palaces – ANNE BOLEYN

Familypedia – Frederik VII of Denmark

Number One London – The Life & Death of Queen Caroline

History – The Wildly Different Childhoods of Elizabeth I and Mary Queen of Scots