There’s a reason why prostitution is called the world’s oldest profession. It has been around for thousands of years in one form or another. Whether for money, trade, or protection, people have been selling their “goods” across the globe since the advent of quid pro quo. Throughout the centuries, numerous ladies of the evening have stood out from their peers as being somewhat more prestigious in their abilities. Here are ten of history’s most prominent prostitutes.

10 Rahab
Jericho

The story of Rahab comes from the Book of Joshua in the Torah and tells of a woman who ran an inn and brothel adjacent to the wall of Jericho during that city’s siege by the Israelites, commanded by Joshua.

Before entering the city, Joshua sent two spies to Rahab’s in order to properly assess the military strength of Jericho. When Jericho’s soldiers went to capture the spies believed to be under Rahab’s roof, she hid the men under piles of flax and barley. She feared the wrath of the Israelites and gave refuge to the spies in order to spare her and her family from death, to which the spies agreed. To mark her home to be spared, she placed a red chord on the door, which some believe may be the origin of the use of a red light to indicate a brothel.

9 Thais
Greece, ~330 BC

Often, the company we keep can be what lands us in the history books. This was certainly true for the likes of Thais, who accompanied none other than Alexander the Great on his many campaigns. It is unknown whether or not Thais “worked” for Alexander, but it is said that he kept her in his company for the duration of his many military campaigns.

Aside from being arm candy to one of the greatest military commanders of all time, Thais also instigated the burning of Persepolis. She gave a speech at the palace of Persepolis and called for its destruction. She was the second person after Alexander to ceremoniously throw a torch into the building. This was likely done as an act of vengeance against King Xerxes of Persia for his destruction of the Athenian Acropolis.

8 Phryne
Greece, 371 BC

Perhaps one of the most famous ladies of the night to come out of ancient Greece, Phryne was a courtesan whose real name was Mnesarete, which meant “to commemorate virtue.” Her real name notwithstanding, Phryne was eventually charged with impiety. She faced her charges with the defense of Hypereides, a famous orator of the time.

When it looked like her trial was leaning toward a guilty verdict, Hypereides exposed his client’s breasts to the court. Seeing her beauty exposed in such a way brought pity to the judges, who proclaimed that they could not sentence to death “a prophetess and priestess of Aphrodite,” and Phryne was acquitted of all charges.

7 Su Xiaoxiao
China, AD 482–501

Su Xiaoxiao, sometimes referred to as “Little Sue,” was a Chinese courtesan and poet who lived during the Southern Qi Dynasty and was well-regarded for both her beauty and intellect. Though she shared her body with the common man, she was best known for her poetry. She died at the age of 19 due to a terminal illness, and when she saw her death on the horizon, she dedicated her remaining time to writing poetry and sharing her beauty with the world.

There are numerous stories of her life, most of which involve her escapades with young men. Her tomb sat undisturbed for centuries until it was destroyed during the Cultural Revolution, but it was finally rebuilt in 2004.

6 Jeanne Becu, Comtesse Du Barry
France, 1743–1793

Madame du Barry was the last chief mistress to King Louis XV of France, who fell victim to the Reign of Terror that arose during the French Revolution.

She began her career in Paris, accumulating a large base of aristocratic men who paid for her services. To become the mistress of the king, she required a title and was falsely married to her brother, while falsified documents claimed her to be three years younger and gave her a fictitious line of noble descent.

Within a year, she was able to elevate her status from a streetwalker to a noble courtesan of the king of France, but timing was not on her side because of the Reign of Terror. Her immediate association with Louis XV almost guaranteed her a date with the guillotine on December 8, 1793.

5 Mary Boleyn
England, 1499–1543

The lesser-known sister of Anne Boleyn, Mary Boleyn often sat in her sibling’s shadow. She was a courtesan and lady in waiting who was known by many in France as “The English Mare” due to her sexual proclivities. Many stories recount the use of her sexuality to gain favors in court, and she was a mistress of both the English and French kings for a time. It is believed that she died around the age of 40 or 41, though her burial site is unknown.

Mary lost the favor of court life after she married a man who was considered to be of a lower status than she was, and when her sister was beheaded, she faded into relative obscurity in France. Her descendants include notable British citizens such as Charles Darwin and the Duchess of Cambridge Catherine (Middleton).

4 Veronica Franco
Italy, 1546–1591

Veronica Franco was a well-educated young lady whose mother taught her the means at her disposal to attract a wealthy husband. While still a teenager, she married a doctor, but it ended badly, and Veronica turned to prostitution at the Venetian Court to survive.

While she delighted the male aristocracy of Venice, she also spent time writing and published several books of poetry. She was so successful in both her professions that she amassed a large fortune and began a charity for her fellow courtesans’ children.

Like others in her line of work, she was charged with witchcraft and was forced to successfully defend herself at inquisition. Her ultimate fate is unknown due to her passing into obscurity, but it is believed that she lost her wealth when she was forced to flee Venice due to plague in 1575. She is believed to have died in poverty following the death of her last benefactor.

3 Mary Jane Kelly
England, 1863–1888

In some cases, it’s not the life you live but rather your death that makes you famous. Mary Jane Kelly is one such woman—the final victim of Jack the Ripper.

The horrors done to her in her final moments of life make her murder stand out above the four that preceded it. Each of the victims were mutilated in some way following death having their throats slashed. Mary Jane Kelley was not as fortunate, as her mutilation was likely carried out while she was still alive. The scene was so gruesome that most who saw it fell ill, and the only known photograph of the scene is believed to be the first ever crime scene photo. Without delving into too much gruesome detail, blood was spattered all over the place, and various organs and pieces of flesh were removed and draped about her body. Her death, like the others in the Ripper case, remains unsolved.

2 Catherine Walters
England, 1839–1920

Catherine Walters, also known as “Skittles,” was considered to be one of the last great courtesans of Victorian London. She was considered to be very beautiful and was also a trendsetter, having elevated the hobby of horse riding for women in Victorian London due to her “Princess riding habit” that the ladies emulated whenever they could.

The list of her male benefactors includes many politicians and a member of the royal family, possibly Edward VII, the eldest son of Queen Victoria and Prince Albert. She was best known for her modesty, which made her a likely candidate for many aristocratic men who wanted their sexual escapades to remain secret. This made her a very wealthy and well-cared-for woman who amassed a considerable fortune, which allowed her to retire in 1890, making her a very rare example of a courtesan who did not die young, impoverished, or in obscurity.

1 Lizzie Lape
United States, 1853–1917

Lizzie Lape was an Ohio madame and prostitute who ran multiple bordellos. Lizzie married eight times, once to her best customer, and is best known for her odd connection to Warren G. Harding, the 29th president of the United States.

Harding worked as a newspaper editor and staged a hoax upon a rival editor, Vaughn, at Lizzie’s most famous bordello, the White Pigeon. Harding was able to coax Vaughn into the brothel and then had the police perform a raid, causing a great deal of embarrassment for the gentleman. It is believed that Mr. Harding was well-acquainted with Lizzie’s houses and may have visited her Red Bird Saloon.

Lizzie was able to hold onto her properties despite multiple lawsuits by ex-husbands. She never lost her houses and ultimately retired on her own terms.

Jonathan is agraphic artist, illustrator, and game designer with a few independently-published games through his game company, TalkingBull Games. He is an Active Duty Soldier and enjoys researching and writing about history, science, theology, and many other subjects.

The world’s oldest profession is featured in films again and again. After all, it’s been said that all stories are made from sex and war. And if that’s the case, then sex workers were always bound to be leading characters.

Sex work, however, is still stuck in the fringes of most modern cultures, and like the fringe itself, its movies can get weird. Most movies featuring prostitutes are either overly tragic or silly, and even the happy ones make questionable choices. They seem to always want us to either pity, mock, or secretly fear sex workers, and a lot of the time, they try for all three.

This list gathers ten of those movies, films about prostitutes that are just bizarre.

Related: 10 Well Known Movies With Bizarre Backstories

10 Bordello of Blood

There is no end to the weird facts about the vampire-prostitute movie Bordello of Blood, both the picture itself and its making. For one thing, the script was one of the very first ever written by a young Robert Zemeckis, better known as the writer of the Back to the Future trilogy and The Polar Express, among others. For another, a weird convergence of business deals led to this movie not being made until 1996, making this silly Dennis Miller-fights-sexy-vampires film Zemeckis’s direct follow-up to his Best Picture-winning drama Forrest Gump.

The movie itself was released as a Tales From the Crypt feature, so appearances from the ever-charming Crypt Keeper bookend it. Other than that, the film has nothing to do with Tales From the Crypt, but branding is branding. Then there’s the movie itself, and it needs to be seen to be truly believed. Essentially, it’s an hour and a half that alternates between Dennis Miller doing the usual Dennis Miller quips and sexy models luring men to their deaths.

9 The Happy Hooker Franchise

The Happy Hooker trilogy is bizarre for a number of reasons. Based on a real-life memoir, the first film follows a well-to-do Dutch immigrant named Xaviera Hollander as her questionable choices and terrible luck drag her down into prostitution and jail. Despite that synopsis, it was meant to be a comedy.

Even further, the film spawned a sequel entitled The Happy Hooker Goes to Washington and a third film entitled The Happy Hooker Goes Hollywood, turning the real-life Xaviera Hollander into the Ernest of call girls. Another bizarre fact is that the third movie is about the fictional version of Hollander attempting to turn her memoir into a movie, making the third film a dramatization of the making of the first film.

8 Sin City

In Robert Rodriguez’s Sin City, as in the original Frank Miller graphic novel series, sex workers are portrayed as badass, leather-clad mercenary ninjas, and frankly: it rocks. The prostitutes control their own slice of the city, a red-light district on crack known as Old Town, in which they govern themselves. They police themselves, as well, eschewing badges and nightsticks for katanas and throwing stars.

Sin City sees prostitutes in charge of their own destiny. It allows them to identify themselves as much by their fellowship and their prowess as by their profession. Even better, it gave us the moment in which Miho kills Jackie Boy and “doesn’t quite chop his head off. She makes a Pez dispenser out of him.”

7 The Best Little Whorehouse in Texas

The Best Little Whorehouse in Texas is a fun, light-hearted musical comedy starring Dolly Parton and Burt Reynolds. It’s also an oddly depressing story by the end.

The basic plot is the same as Roadhouse, in which a powerful local politician attempts to shut down a beloved business staffed by a crew of underdogs. Unlike Roadhouse, however, The Best Little Whorehouse in Texas doesn’t win. The movie ends with the brothel, despite fighting for its existence the whole movie, being closed down for good. For some reason, Parton’s character shrugs off the loss of her life’s work just because someone proposes to her. And the other prostitutes don’t even get that; they lose their livelihood and home, receiving nothing in exchange.

6 (The Real) Pretty Woman

If asked to think up a movie about prostitutes, it’s likely that Pretty Woman would be most people’s answer. The movie is iconic, and it is remembered in part for its hopeful, happy ending in which Julia Roberts’s character is plucked from the streets and saved from her dismal life as a prostitute. Bizarrely, the original ending of the film was the exact opposite.

Pretty Woman was initially entitled “3,000,” and it was apparently too dark to be made as it was. Though the theatrical version ends with Richard Gere’s character falling in love with Roberts’s Vivian and elevating her to the high life, the original is bleak. Gere’s character simply tosses Roberts out of his limo into a dirty alley, throws her money on top of her, and speeds away.

5 The Girlfriend Experience

In 2009, acclaimed director Steven Soderbergh felt a truly bizarre itch he needed to scratch, and thus he made The Girlfriend Experience. The film is a wandering series of slice-of-life scenes about a New York City prostitute who finds herself selling companionship and conversation more than sex. It also starred then-pornstar Sasha Grey.

Fans of Grey’s earlier work might be disappointed upon watching the film, and anyone else might be too. The movie is worth a viewing if only to provoke the questions, “What are we watching?” and “Is this terrible or excellent?”

4 Taxi Driver

Taxi Driver is truly a cultural landmark. The movie is often included in lists of the best films of all time and is frequently cited as one of the best in the filmographies of both Robert De Niro and Martin Scorsese, which is saying quite a lot. It is also notable for introducing most of the world to a young Jodie Foster, whose role in the film was an abused 12-year-old prostitute.

Iris’s character is about as tragic as any, and saving her becomes one of the only redeeming goals that De Niro’s protagonist displays. While this film is about obsession, stalking, and mental illness, it also finds an unusual sentimentality in the form of an exploited child prostitute.

3 Risky Business

Risky Business has endured in pop culture mainly for the iconic scene in which a young Tom Cruise finally gets his parents’ house to himself and celebrates by sliding across his hardwood floor in his tighty-whities. Because of that moment’s popularity, the film’s actual plot tends to take a backseat.

Risky Business is about a high-school boy running a brothel out of his parent’s house for almost exclusively high-school-age clients. Cruise’s character ends his journey by being accepted to Princeton, based almost completely on the fact that he bribed the university’s interviewer with prostitutes. For a teen comedy, it’s a bizarre premise.

2 Midnight Cowboy

If Midnight Cowboy had been released in 2021, it would still be considered an excellent film but would otherwise be unremarkable. The artistic and political climate in today’s United States would accept Midnight Cowboy as it has hundreds of hundreds of poignant dramas about lost souls and urban alienation. But Midnight Cowboy was released in 1969, and if you’re not familiar with the movie, its reception was truly bizarre.

The film stars Jon Voight as a male prostitute and makes it clear that he isn’t picky about the gender of his clients. In 1969, this earned the film an X-rating, a label that’s reserved almost exclusively for porn today. The reasoning then was its “homosexual frame of reference” and “possible influence upon youngsters.” Even crazier than a normal drama film getting this kind of rating, the X-rated movie won the Oscar for Best Picture. To this day, it remains the only X-rated picture ever to win the coveted award.

1 Frankenhooker

If you have not seen Frankenhooker, put it on right now. Warning: nudity, gore, and the silliest special effects ever to make it to a final cut.

Frankenhooker is a B-movie horror-comedy, and it leans into the genre’s absurdity more than most. The movie’s plot follows a scientist whose fiancé tragically dies by being sucked into a lawnmower. The scientist then decides to reanimate her using only the most attractive body parts collected from prostitutes. He kills the women with a special brand of crack cocaine he has created that causes users to explode. The reanimation goes awry, and his fiancé becomes a murderous monster.

There are more twists, including one last “horrific” surprise in the film’s last moments, guaranteed to provoke a belly laugh. If nothing else, the fact that Bill Murray once publicly said of the film, “If you see one movie this year, it should be Frankenhooker” ought to encourage a watch.