English actor Charlie Chaplin (1889 – 1977) was the silent film era’s most famous and beloved star, and one of the silver screen’s all-time greats. However, there was a creepy side to him. In addition to being a pioneer who revolutionized acting and comedy, Chaplin was also a pervert who liked ’em young. So young as to cause scandal, derail his career, and get him de facto deported from the US. He was also a Harvey Weinstein type before there was a Harvey Weinstein. Chaplain reportedly pioneered the “casting couch”, whereby powerful Hollywood figures extracted explicit favors from actresses during auditions. He used caption cards in auditions to prompt aspiring actresses into increasingly suggestive acts and poses until they stood before him naked or nearly so.
That kind of predation however was run of the mill. He had other kinks that went beyond the usual quid pro quo harassment, and into the realm of the… unusual. Among other things, Chaplain had a thing for pies – and not just as comedic props and gags. After he got actresses to disrobe amidst their auditions, Chaplin would grope them in exaggerated ways on the couch. Then, after he had worked himself up by getting them to do a striptease on demand, followed by a groping session on the couch, he would stand them naked against a wall and throw pies at them. That seemed to do it for him.
Charlie Chaplain also had a penchant for… group activities. Naked ones. He liked to organize them with his friend and fellow comedic film star, Fatty Arbuckle – who has his own scandalous entry, below. Those activities came to an abrupt halt in the aftermath of a scandal that rocked the country in 1921 when Fatty Arbuckle was accused of an assault that led to a woman’s death and was tried for murder. Although acquitted, the Chaplin-Arbuckle parties never resumed. Chaplin’s greatest scandals however arose from his propensity to rob the cradle: he liked much younger women.
FBI Director J. Edgar Hoover, a pervert himself if ever there was one, had long disliked Chaplin’s political leanings. So he used the actor’s scandals to launch a smear campaign against him. In 1944, he had Chaplin prosecuted for violations of the Mann Act, which prohibits the transportation of women across state lines for explicit purposes. Chaplin was acquitted, but his reputation was severely damaged. In 1952, while Chaplin was in London for a film premiere, the US Department of Justice revoked his visa. To gain re-entry to the US, he would have to submit to an interview about his politics and morality. Chaplain decided not to bother, cut his ties with America, and settled in Switzerland.
Charlie Chaplin’s BFF in Hollywood used to be Roscoe Conkling Arbuckle. Better known as Fatty Arbuckle (1887 – 1933), he was a comedian, director, screenwriter, and early superstar actor in the silent film era. A heavy man who weighed about 300 pounds, Arbuckle incorporated his heft into his comedy as he moved gracefully, tumbled, threw pies, and behaved as an all-around lovable and jolly fat guy. In addition to being an actor, Arbuckle was a Hollywood mover and shaker. He mentored Charlie Chaplin, with whom he formed a close personal friendship.
Arbuckle also discovered and launched the careers of future stars such as Buster Keaton and Bob Hope. Things got awkward for the Chaplin-Arbuckle friendship, however, when a scandal struck and destroyed Fatty’s career and reputation. It began with a wild party at a San Francisco hotel, where Arbuckle and friends rented adjacent luxury suites in September of 1921. Several women were invited, and at some point amidst the revelry, an aspiring actress, Virginia Rappe, was found seriously ill in one of the suites.
The hotel’s doctor examined Virginia Rappe, concluded that she was incredibly intoxicated, and gave her morphine to calm her down. As it turned out, the situation was more serious. Two days after the San Francisco hotel party, Rappe was rushed to a hospital. There, a friend claimed that Fatty Arbuckle had assaulted her at the party. The next day, Rappe died of peritonitis, caused by a ruptured bladder. Although medical examinations found no evidence of assault, newspapers nonetheless had a field day.
The press, no less restrained in the Roaring Twenties than it is today, printed increasingly salacious stories about Rappe’s death and left no awkward angle unexplored. Some alleged that Arbuckle had killed Rappe with his weight when he got on top and assaulted her. Other stories claimed that Fatty had penetrated Rappe with a piece of ice. The ice assault take eventually grew into accusations that Arbuckle had ruptured Rappe’s insides when he penetrated her with a bottle of Coca-Cola or champagne.
Police investigators went with the theory that the heavy impact of the overweight Fatty Arbuckle’s atop Virginia Rappe during intercourse had caused her bladder to rupture. Arbuckle found himself in an increasingly bad situation and truthfully denied that he had done any wrong. It did him no good, and amidst a public furor whipped by an unscrupulous press and an even more unscrupulous prosecutor, he was arrested and charged with manslaughter. Initially, San Francisco’s District Attorney had wanted to try Arbuckle on a first-degree murder charge, and seek the death penalty.
The resultant criminal case was a major media event – the OJ Simpson scandal of the day. Those who knew Arbuckle regarded him as a good-natured man, who was shy. As some put it, he was “the most chaste man in pictures“. His friend Charlie Chaplin stated that he “knew Roscoe as a genial and easy-going man, who would not harm a fly“. However, after the Rappe scandal erupted, newspapers went with a far different image. The hitherto beloved comic actor was now depicted as a gross pervert, who routinely used his massive bulk to overpower and force himself upon innocent girls.
19. Innocence Did Not Save This Once-Beloved Actor’s Career
The criminal case against Fatty Arbuckle fizzled when evidence of prosecutorial misconduct emerged. As it turned out, San Francisco’s District Attorney, an ambitious man with plans to run for California governor, had pressured witnesses into lying. The defense also obtained an exculpatory letter from the state’s star witness, Virginia Rappe’s friend who had first leveled accusations of assault. In it, she admitted that she had planned to extort money from Arbuckle. In the trial, the state produced little credible evidence, and medical experts demonstrated that Rappe’s bladder had been ruptured by an internal inflammation, not by an outside force.
The jury deadlocked 10-2 in favor of acquittal, and a mistrial was declared. A second trial again ended in a 10-2 deadlock in favor of a not guilty verdict. A third trial was launched, and at its conclusion, the jury took just six minutes to return a unanimous verdict of not guilty. Arbuckle was thus exonerated, but his company in Hollywood was now not only awkward but outright toxic. His reputation and standing never recovered, and his career was effectively destroyed.
18. An Awkward Revelation About a Hollywood Heartthrob
Hollywood silent film era superstar Rudolph Valentino (1895 – 1926), also known as “The Latin Lover”, was a 1920s’ symbol of masculinity. He shot to fame with performances in silent film blockbusters such as The Sheik, and The Four Horsemen of the Apocalypse. His sudden death at the young age of thirty-one resulted in mass hysteria among his female fans and solidified his iconic status. However, there was an awkward fact about the beloved actor that had been little known in his lifetime. Before he became a star, Valentino had probably been a male prostitute. He had worked as a dancer in what was known as “taxi dance clubs”. Such clubs were basically escorting services, where clients would come in, examine the club’s stable of dancers, and pay to dance with whichever one caught their eye.
Clients who got good vibes and liked their dance partner would negotiate a price with him or her, then pay the club an “exit fee” to leave with the dancer. Some taxi dance clubs were legitimate and innocent, but most were just straight-up escort services. In Valentino’s case, he was once arrested in a brothel before he became famous, so it is unlikely that his taxi dance club was the innocent kind. To put it in perspective, imagine if it was discovered that Brad Pitt had been a gigolo or male prostitute who had worked for an escort service. The paparazzi stampede would have caused an earthquake. The ensuing media and social media firestorm would probably have broken the internet, as the insatiable demand for salacious details produced a flood of stories.
The famous Austrian neurologist Sigmund Freud is widely acknowledged as the father of psychoanalysis and psychotherapy. We have him to thank for the psychiatrist couch, and the payment of hundreds of dollars an hour for somebody to nod his head as he listens to us drone on about our lives, before prescribing us some happy pills. Freud basically said that we are all perverts, and that deep down, all guys want to murder their fathers in order to clear the path for intercourse with their own mothers.
Ironically, the figure he chose to name that complex after was probably the least Oedipal person ever. In Greek mythology, Oedipus went to extreme lengths to avoid a prophecy that predicted he would murder his father and marry his mother. He only ended up doing so unwittingly, after a series of extraordinary flukes. Freud, by contrast, was pretty Oedipal himself, as he openly acknowledged the awkward fact that he had lusted after his mother. That paled in comparison to Freud’s theory that the root cause of child molestation was not adults who preyed upon children, but children who lusted after their parents.
16. The Seedy Misadventures of the Prince of Wales
Albert Edward (1841 – 1910), the eldest son of Queen Victoria and her consort Prince Albert, went on to succeed his mother on the throne and reign as King Edward VII from 1901 until his death. He was no great shakes as a ruler and was a mediocrity both as a man and as a monarch. As a libertine, freak, and all-around royal pervert, however, he shone. He stood in stark contrast to his notoriously straitlaced mother, who lent her name to an uptight and prudish age.
As he grew up, Albert, or “Bertie”, was a disappointment to his prim and proper parents. The first letdown arrived when Bertie was sixteen-years-old and had his first scandal with a prostitute. The queen was not amused, and the conversation must have been as awkward as awkward gets. Bertie did not mend his wayward ways, and after another scandal, his father went to chastise him. On the way back, he caught a severe bout of pneumonia, which did him in. For the next four decades, Queen Victoria blamed Bertie for the death of her beloved husband, and actively tried to prevent his succession to the throne.
Queen Victoria failed to get her eldest son removed from the line of succession. However, she often remarked that her longevity and long reign were due to her determination to outlive Bertie and prevent him from ever becoming king. She tried hard and did her best, but after a reign that lasted for sixty-four years, Victoria finally died in 1901. After a long wait that he thought would never end, Bertie became King Edward VII at age sixty. In those long decades, Bertie became notorious for his relentless quest to gratify his intimate appetites. Whether cheap hookers, top-notch French aristocratic ladies and courtesans, discrete liaisons, well-publicized affairs with famous actresses, swinger-wife swap orgies, Bertie was insatiable and down for it all.
He was a big fan of Paris’ elite brothels, especially its most exclusive house of night, La Chabanais. There, he had his own room, decorated with his coat of arms and furnished to his specific tastes. Said tastes included a specially designed chair, named siege d’amour, which he had installed in his private brothel room. By the 1890s, Bertie was an obese, middle-aged, and out-of-shape man. So he had the heavy-duty love chair custom made to bear much of his weight, and enable him to do the deed without crushing his partners. It also positioned his partners just right for royal access, with minimal exertion and contortions on his part.
14. Ireland’s Greatest Writer and His Awkward Kink
James Augustine Aloysius Joyce (1882 – 1941) is probably Ireland’s greatest man of letters. The author of the innovative novels Ulysses and Finnegan’s Wake was a modernist writer who wrote in a groundbreaking style. In it, he combined complexity with explicit content that shocked contemporaries and led to landmark legal decisions on obscenity. Since creative genius is so often accompanied by odd and awkward behavior, it should perhaps come as no surprise that James Joyce was also a total weirdo.
Joyce had a thing for breaking wind – farts, if you will. He just loved farts to distraction, and could not get enough of them. Whether he dished them out, preferably on people’s faces, or received them, farts made Joyce’s day. His enjoyment of farts was not limited to the fine pleasure of experiencing them. As a world-class author, he had to write about farts, and describe them in exquisite detail. Indeed, there is an entire collection of Joyce letters in which he writes passionately about cutting the cheese.
To get an idea of James Joyce’s awkward fascination with farts, consider this excerpt from a letter to his lover: After talking explicitly about making love to a farting woman, he goes on to say, “I think I would know Nora’s fart anywhere. I think I could pick hers out in a roomful of farting women. It is a rather girlish noise not like the wet windy fart which I imagine fat wives have. It is sudden and dry and dirty like what a bold girl would let off in fun in a school dormitory at night. I hope Nora will let off no end of her farts in my face so that I may know their smell also.”
For years, Joyce struggled with acute anterior uveitis, an inflammation of his iris. Later, he developed glaucoma due to these episodes. Lingering pain left him unable to read or write for weeks. Joyce underwent numerous procedures and surgeries to try and remedy his recurring eye problems. He also suffered acutely from syphilis. But the thing that did him in was the after-effects of surgery performed on his perforated ulcer.
Romeo and Juliet are probably the world’s best-known star-crossed lovers. However, they are fictional characters, conceived in the imagination of William Shakespeare and brought to life by his quill. For real-life star-crossed lovers, perhaps none are more famous than Heloise and Abelard. A pair of medieval scholars, their romance ended in a painful manner – especially for him – as it gets. Peter Abelard (1079 – 1142) was born into minor French nobility in Brittany, and from an early age, he exhibited a love of knowledge that marked him for a life of scholarship.
Abelard’s father encouraged him to study the liberal arts, and by his early twenties, he was famous for his debate skills, particularly in philosophy. Like some super smart people, however, he also gained a reputation for arrogance. By 1115 Abelard was an accomplished theologian, the master of Notre Dame, and a canon in the archdiocese that included Paris. That was when he ran into Heloise d’Argenteuil (circa 1095 – 1164). She lived in the precincts of Notre Dame under the care of her uncle, a secular canon named Fulbert.
A rarity among women in her day, Heloise had mastered Latin, Greek, and Hebrew, and gained renown for her knowledge of classical studies. To get to her, Abelard wormed his way into the household of her uncle, Fulbert. He claimed that he could not afford a place of his own, and offered to tutor his niece in lieu of rent. Fulbert agreed, tutor and student soon hit it off, and in 1115, Heloise and Abelard began an affair. It was torrid and given their circumstance, the duo were too blinded by their passion to pay heed to the risks involved.
Heloise lived in convent, but she snuck out, or he snuck in, whenever possible. They got physical whenever and wherever they could. They made love in gardens at night, in her convent cell, in the nunnery’s kitchens, and in her uncle and guardian’s bedroom. She eventually got pregnant, and the couple found themselves in an awkward situation. So Abelard arranged for her to visit his family in Brittany. There, she gave birth to a son. Unfortunately for the lovers, and especially for Abelard, his arrogance betrayed him: he started to boast of his conquest. That backfired on him in a major way.
10. An Affair That Ended With the Unkindest and Most Awkward Cut of All
Word got back to Fulbert, Heloise’s uncle and guardian, about Abelard’s boasts, and things took a turn for the worst. To appease Fulbert, the duo got secretly married. When her uncle disclosed the marriage, however, Heloise denied it in an attempt to protect her husband’s career. Abelard sent her to a convent to protect her from her uncle, where she pretended to become a Bride of Christ. Her uncle interpreted that as Abelard’s attempt to bury the awkward scandal by forcing Heloise to become a nun. Enraged, he set out to make Abelard pay for the defilement of his niece.
Fulbert hired some thugs to break into Abelard’s room one night, where they beat him up. Then, they dealt the scholar the unkindest cut of all, and castrated him. After he recovered from his injuries, Abelard became a monk and retired to a monastery. He cajoled Heloise, who was reluctant to don the habit, into becoming a nun for real. Eventually, Abelard got over the trauma and resumed his career as a lecturer and writer. Heloise became prioress of her convent, and the duo spent the rest of their lives writing each other letters.
George Gordon Byron, 6th Baron Byron (1788 – 1824), was one of the most prominent figures of the Romantic Movement. Today, he is acknowledged as one of Britain’s greatest poets, widely praised for his brilliant use of the English language. His private life, however, was chock full of awkward material. Byron was famous – or infamous – for his flamboyance, deviant practices, the notoriety of his romantic liaisons with members of both sexes, and allegations of incest. Of the great poet’s numerous affairs, his most famous was with the married Lady Caroline Lamb.
She gave him the cold shoulder at first, and described him as “mad, bad, and dangerous to know“. Eventually, she succumbed to his charms and joined him in a torrid affair that scandalized Britain. After he dumped her, Lamb turned stalker and pursued him relentlessly. After she stopped at his house one time too many and scribbled in a book on his desk “Remember me”, an exasperated Byron responded as only a poet could. He composed a poem entitled Remember Thee! Remember Thee!, whose final line concludes “Thou false to him, thou fiend to me“. Byron’s most controversial relationship however was an incestuous one carried on with his own sister, Augusta Leigh.
Byron had seen little of his sister Augusta Leigh in their childhood. He made up for it in spades when he formed an extremely close relationship with her in adulthood. In 1814, Byron fathered a daughter upon his sister, which made for an awkward family relationship in which the poet was the unfortunate child’s uncle, as well as her father. It goes without saying that he was not faithful to his sister, and carried on a plethora of other affairs. Byron, ever sentimental, liked to keep mementos of his lovers. In those days, the norm was a lock of hair from one’s object of affection, perhaps tied with a ribbon. For Byron, Britain’s most flamboyant poet, eccentric aristocrat, and all-around pervert, a simple lock of hair would not do.
Instead, Byron liked to snip clumps of pubic hair from his lovers’ crotches, and kept them, cataloged and labeled, in envelopes kept in his publishing house. The cascade of scandals eventually made Britain too hot for Bryon. So he traveled around Europe for years at a stretch. He spent a seven-year stint in Italy, before his restlessness led him to join the Greeks in their war of independence from the Ottoman Turks. He was disappointed with the Greeks of his day, however, because they differed greatly from the heroic Hellenes he had read about in history books and Homer’s poems. While he moped about that discrepancy like only a romantic poet could, he caught a fever and died in a Greek backwater at the age of thirty-six.
Eric Gill (1882 – 1940) was a celebrated English sculptor, printmaker, and typeface designer. Many of his fonts are still in use today. He played a prominent role in the anti-industrial Arts and Crafts Movement that flourished in the late nineteenth and early twentieth centuries, and which popularized the use of folk styles of decoration. For his creative endeavors, Gill was named Royal Designer for Industry – Britain’s highest award for designers. A lesser-known but awkward fact about Gill – as in the extremely icky kind of awkward – is that he was a total creep.
Gill was a man of many contrasts, to say the least. In 1913, he converted to Catholicism. As with many newcomers to faith, he became a zealot, and loudly and ostentatiously professed devoutness to his new creed. With his wife and others, he founded a lay religious order called The Guild of Saint Joseph and Saint Dominic. He went about clad in a habit, with a girdle of chastity beneath. The chastity girdle was probably aspirational because it did not stop him from being a totally unchaste pervert.
6. There’s Pervy, and Then There’s This Sculptor’s Level of Pervy
Eric Gill was obsessed with making love and liked to work it into all his work. His obsessions did not revolve around normal intercourse: he was into incest, bestiality, and pedophilia, was addicted to prostitutes and liked to abuse his maids. One of his most famous sculptures, Ecstasy, depicts a couple passionately entwined. The model was his sister, with whom he had a lifelong incestuous relationship, and her husband. Some of his most celebrated artwork used his own prepubescent daughters as models.
Gill liked to draw his daughters nude, in semi-erotic poses. In his diary, he described his perversions with great relish and in exhaustive detail. Extramarital affairs, decades of intercourse with his sisters, incest with two of his daughters, and bestiality with his dog, he penned it all. In short, Britain’s most celebrated sculptor and one of her greatest artists of the modern era was the kind of person who would probably be in jail or on an offender registry if he was alive today. That makes modern appreciation of his artistic talents pretty awkward, to say the least.
Presidential hanky panky is an irresistible magnet for the media and the public. Just ask Bill Clinton about the firestorm of interest in his affairs. Or ask Donald Trump about the accusations that dogged him throughout the 2016 presidential campaign, dogged him throughout his presidency, and continue to dog him today. However, those firestorms would probably look like dim candles compared to what would have erupted if the affair between JFK and Marilyn Monroe had happened today. Rumors had swirled for quite some time about an affair between President John F. Kennedy and America’s most iconic symbol. Marilyn’s sultry “Happy Birthday” performance for JFK on his forty-fifth birthday did nothing to still the gossip.
To make things more awkward for the POTUS, his wife was present as Monroe crooned to him. Although tongues wagged, JFK was extremely lucky not to have his affair turn into a firestorm. The media of his era was far more discreet than today’s press. Nonetheless, the gossip caused Kennedy to back away from Monroe and end things – to him, she was just one among dozens of pretty women he had slept with. To Monroe, he was the only president she had slept with, and she was not about to give up that easy. She repeatedly called the White House and tried to rekindle the affair, until JFK sent somebody to convince her that it was over and that she needed to stop.
4. Make That a President and The President’s Brother’s Awkward Affair
If it happened today, the aftermath of the affair between JFK and Marilyn Monroe would have made things even more awkward for the White House. It would have added even more fuel to what would have already been an inferno of insatiable media and public interest. After JFK tired of the blond bombshell, he essentially passed her on to his younger brother and the United States’ Attorney General, Bobby Kennedy. Robert F. Kennedy was widely viewed as the most straitlaced and family-oriented of the Kennedy brothers. RFK’s image was that of a happily married and devoted husband, who raised a large and steadily growing family that would eventually number eleven children.
The contrast between that public perception and an affair with the world’s greatest sensual symbol would have added fuel to the scandal. Then add to it Marilyn’s unexpected death in 1962. The Los Angeles coroner’s office ruled the death a probable suicide via barbiturates. Conspiracy theories abounded however and included allegations that JFK or RFK had been involved. The sudden death of a former mistress of the president, with whom he had an affair while in office, and who then became the mistress of his brother, the Attorney General and the president’s right-hand man? Such a scandal would break the internet if it happened today.
Emperor Napoleon Bonaparte was not as murderous as Genghis Khan or Hitler. In his day, however, the French ruler was feared and loathed by his foes just as much as contemporaries feared the Fuhrer and the great Mongol conqueror. As he roamed Europe at the head of his armies and gobbled up countries as if they were popcorn at a movie theater, Napoleon was scary enough to serve as a boogeyman. Indeed, English parents used to scare their children into obedience with “Boney the Bogeyman”.
Le Empereur, who was often derided in newspapers read by adults as “Little Boney” in a bid to belittle and play down his threat, was portrayed as a larger-than-life figure to England’s kids. He was portrayed as a giant ogre who would take away naughty children and eat them for breakfast. “If you don’t behave, Boney will come for you” often sufficed to get rambunctious youngsters to pipe down. For such a scary figure, it is surprising that he was once routed by an army of small opponents. Napoleon was famously defeated at Waterloo, but it was not his only loss. A smaller – albeit perhaps more awkward – defeat was once dealt Boney by, of all things, bunny rabbits.
The Battle of Waterloo in 1815 was Napoleon’s worst defeat. However, his most awkward loss was dealt him years earlier, when the mighty Bonaparte was put to flight in a bizarre incident by a horde of cute bunny rabbits. It happened in 1807 when he was at the height of his power and bestrode Europe like a colossus. He had vanquished the Austrians and Russians at the Battle of Austerlitz and humiliated the Prussians at the twin battles of Jena-Auerstedt. He capped off his victories with the Treaties of Tilsit, which ended the War of the Fourth Coalition against him.
In an understandably good mood, Napoleon decided to celebrate, and what better way to celebrate than to kill small animals? So Napoleon ordered his chief of staff, Alexander Berthier, to arrange a rabbit hunt and invite the top military brass. Berthier prepared an outdoor luncheon and collected about 3000 rabbits. They were arranged in cages along the fringes of a grassy field, to be released for the bigwigs to shoot as they fled. It went wrong, however. When the bunnies were released they did not jump away in terror, but bounded in their thousands towards Le Empereur.
As thousands of bunnies bounded towards them rather than flee for their lives, Napoleon’s party laughed at first. The laughter stopped and concern grew, however, as the onslaught continued. The rabbits swarmed the Emperor’s legs and climbed up his jacket. He tried to shoo them with his riding crop, while those around him tried to chase them away with sticks. There were just too many of them, however, and Napoleon was forced to flee to his carriage. As one account described it: “with a finer understanding of Napoleonic strategy than most of his generals, the rabbit horde divided into two wings and poured around the flanks of the party and headed for the imperial coach“.
Even in his carriage, Napoleon was not safe. Some rabbits jumped in with Le Empereur, who ordered his coachmen to whip the horses into a hasty retreat. In an awkward defeat, Europe’s hegemon had been beaten by bunnies. It turned out that the bizarre debacle had been Berthier’s fault. Rather than capture wild hares, he had bought tame rabbits from nearby farms, that were accustomed to people. When released from their cages, they did not fear Napoleon’s party as potential predators. Instead, they bounded towards them in the expectation that the Emperor of the French and his companions would feed them their dinner.
Where Did We Find This Stuff? Some Sources and Further Reading