The Shady Lady of the Night is a prostitute who is hired by someone not for sex, but something else.
Well, not just for cuddling and talking, but something else.
She is hired to do criminal, or...shady activities.
Often they are commissioned to kill or steal from somebody: usually someone important, e.g. a politician or a crime leader. The main idea is that when politicians and crime leaders take the services of a prostitute (that is, the sex part) they allow her to get intimate with them (of course) and are unsuspecting her of any ill will. Especially if this girl is a courtesan, and her clients treat her like their girlfriend, then they are all the less suspective of her, when say, she drops a few spills of something in the food, or brings handcuffs to "have fun" in the bed, or asks a great amount of money for a new bracelet.
In a military setting, this can be possible because of Camp Followers.
Sometimes their target is not at all important: perhaps a woman cheated on by her husband with a prostitute, asks another one to kill her husband, or just do something plainer, like steal his wallet.
Or perhaps, she hires her to spy on him.
A lot of times these prostitutes are asked to be an informant on someone: yes, those politicians and crime leaders, who aren't suspective of her enough, and will talk about their activities with their friends right in front of her.
Many a time she doesn't even need to "spy" on or target anyone: if she is already involved in the criminal world, people (usually an Amateur Sleuth) will just pay her to give out information on those dealings.
This may not be a one-time experience, and she might become a part-time assassin, or informant. Or it could also happen that a brothel is actually a complete information network/assassin ring, in which case that has always been their job besides normal prostitution.
She might be a Dirty Harriet, who goes undercover as a prostitute, but isn't actually one, although if she goes undercover to do shady things, then that would still fit here.
May overlap with Platonic Prostitution, although in this case, sex is usually involved, just not with the original commissioner.
Compare Predatory Prostitute, who is always an evil person, no matter what. A Shady Lady of the Night can have any moral alignment; they are paid to harm someone, but this can range from the least harmful (e.g. giving out sensitive information) to the most (i.e. killing them).
May overlap with the Honey Trap, Femme Fatale, and Out with a Bang.
Not to be confused with Sex for Services, which is where sex is offered as payment for a service.
Examples:
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Anime & Manga
- Fullmetal Alchemist: Colonel Roy Mustang uses the girls in his aunt's (and adoptive mother's) brothel as an information network.
Comic Books
- One of the Road to Perdition stories has Michael O'Sullivan visiting an underage prostitute named Juana whom he wants information from concerning his nemesis Connor Looney. For obvious reasons, he doesn't do anything with her, but instead gets the information that he needs from her and leaves her with enough money to leave if she wants to.
- Sin City: In "The Big Fat Kill", the girls of Basin City's Red Light District are also one of the city's many gangs. A full-on war ensues between them and another gang after they mistakenly kill a police officer (the abusive ex of one of the girls), giving the other gang blackmail material.
Fan Works
- Played With in The Keys Stand Alone: The Soft World. At the Border Crossroads Inn, George and John need to get some information from a waitress. While she's not willing to go up to their room with them to have sex, she agrees to come when they explain they just want information and will even pay her. However, for a complicated reason, another woman is sent along with her, and the woman is a known tattler who will immediately report any shenanigans to the persons currently running the inn. So George has to have sex with the tattler to distract her, while John, who can't have sex with human women anymore, has to fake it while he telepathically interrogates the waitress. Hilarity Ensues.
- The Night Unfurls: Chapter 7 of the original features Kyril visiting the Rosie and its mistress Shani, who is said to have connections with one of Alicia's wayward knights. Rather than for sex, he's here to gather the intelligence needed to strike back at Arc Villain Beasley and his forces.
Films — Live-Action
- Chloe: Initially, Catherine pays Chloe just to meet her husband at a cafe and see if he flirts with her. Later subverted, however it turns out Chloe's lying about having sex with him.
- In Clegg, Wildman employs a former blue movie actress named Suzie the Slag as his personal assassin.
- In Dirty Work, Mitch gets back at a jerkass owner of a used car lot by hiring a bunch of prostitutes to get in the trunk of his cars and pretend to be dead during the broadcast of a live television commercial. Later in the film, Mitch hires the same prostitutes to act as security while getting revenge on the Big Bad.
- Lethal Weapon: Dixie the prostitute was hired to seduce Amanda Huntsacker and give her barbiturates laced with drain cleaner, which would have killed her if she hadn't taken a swan dive while on a drug high, ending her life in a very visible way, and getting the police involved well ahead of when the drug syndicate planned for.
- The Man with the Iron Fists: In the last act of the film, Madam Blossom is hired by the Lion Clan to conceal the Emperor's stolen gold beneath the Pink Blossom Brothel in exchange for a percentage. She double-crosses them: the ladies of the Pink Blossom brothel turn out to moonlight as an assassin-trained Amazon Brigade, kill several members of the Lion Clan in bed and then become one of the participants in the Mêlée à Trois that ensues as the obligatory Quentin Tarantino bloodbath ending.
- Mr. & Mrs. Smith (2005): In the film's prologue, Jane Smith disguises herself as a hired dominatrix in order to get close enough to a mob boss she's been hired to assassinate.
Literature
- Anita Blake: In an early book, Anita needs some information from someone who happens to be a prostitute — she was previously a suspicious man's mistress. It takes Anita quite a while to convince her that, really, yes, she really, truly, actually wants to talk.
- The Ascendant Kingdoms Saga: Female lead Kestel Falke was a highly sought-after courtesan in Donderath but also moonlighted as an assassin who specialized in killing unfaithful or abusive husbands. She was eventually caught and exiled to Donderath's Penal Colony Velant, which is where she met the other protagonists.
- In Brig Scarlet Flamingo, two best brothels on Las Estrellas double as rivaling secret agent bases. Two of their best prostitutes and agents, Eua-le and Lidia, eventually leave the brothels altogether to continue with their spying and sabotaging jobs in the war-torn country of Courbarte.
- Kushiel's Legacy: This is Invoked when Delaunay buys Phedre's indenture and that of Alcuin. He raises them both to be courtesans (which is considered an honored and almost priestly profession in their country) but adds plenty of other lessons in observation, languages, acrobatics, escape, and other espionage tricks of the trade so that he can use them to spy upon and report the goings on of the Deadly Decadent Court. Delaunay's methods are shady but his intention is benign: The late prince was his boyfriend, and he swore to protect his lover's young child, Crown Princess Ysandre, from internal intrigues that would harm her.
- This happens in Lord John and the Private Matter, a spinoff of the Outlander series. Lord John patronizes a prostitute, but not for her services. He wants information about one of the whorehouse's clients.
- In Rebuild World, Carol works as a high-class prostitute in the slums of Kugamayama City. In addition to charging millions of aurum for a single night with her, she also coaxes valuable information out of her clients to sell to other hunters, making her a valuable Knowledge Broker.
- A Song of Ice and Fire: In A Dance with Dragons, the thought-to-be dead Mance Rayder is tasked by Melisandre to save Arya Stark from her marriage with Ramsay Bolton in Winterfell. To do this, he takes six spearwives with him, who go undercover as camp followers (that is, prostitutes serving soldiers). The spearwives kill several men in Winterfell and later help Theon to save "Arya", who is actually Jeyne Poole.
- Vorkosigan Saga: In Captain Vorpatril's Alliance, By reveals that Impsec often recruits prostitutes to work as spies. Their logic is that it is easier to convince a prostitute to act as a spy than to convince a spy to sleep with an enemy target when necessary.
- In The Year of the Rat, a prostitute in Moose Pits is also a Professional Killer hired to hunt down the main characters because of a secret letter they have in their possession. However, Alk figures her act out immediately, since no actual prostitute would flirt with a barefoot mercenary and offer him an unrealistically large discount when a merchant is walking just ahead of him. When he manages to defeat her and get her to confess, she tells him he was the first to do so and offers to continue with the sex, but Alk refuses.
Live-Action TV
- Better Call Saul: Saul hires the prostitute Wendy to ruin Howard Hamlin's reputation by making it seem like Howard had been Wendy's john.
- Breaking Bad: Wendy the hooker is often hired to go above and beyond her usual "services." She's paid to provide Jesse with an alibi to keep him from getting arrested for shooting Tuco; later, Jesse hires her to poison two drug dealers he wants dead with the fast food she usually brings them (though Mike puts a stop to that plan before Wendy can go through with it, letting her go and capturing Jesse instead).
- In Filthy Rich, after relocating to New Orleans and becoming enmeshed in the Monreaux family, Ginger Sweet orders her webcam girls to start keeping recordings of any high-powered religious men who visit their cams, in case she needs to blackmail one of Margaret Monreaux's wealthy, powerful friends, as she suspects that Margaret is looking for any excuse to shove her out of the family. This backfires terribly when Margaret finds out that the Governor of Louisiana is a regular on Ginger's site; Margaret is in a feud with the Governor and thus leaks incriminating footage to the press, which ruins him but also ruins Ginger, as no one's going to visit her website if they think they're being recorded.
- Game of Thrones: Littlefinger runs a brothel whose prostitutes often spy and collect information on their wealthy clients. Ros turned out to actually be a spy for Varys, for which he sold her to the sadistic Prince Joffrey and her death. He replaced her with Olyvar, who went on to spy on Loras Tyrell.
- In the MacGyver episode "The Assassin", the eponymous assassin would hire call girls to do small errands for him, such as picking up a suitcase in the park. He would later kill them.
- In the House episode "A Pox on Our House", House hires a camgirl for a private session, which it turns out is for her to translate a document from Dutch without going through the official hospital channels. Geerte is quite bemused at such a prosaic request but turns out to be a skilled translator.
Video Games
- Assassin's Creed:
- Assassin's Creed II: Sister Teodora and her "congregation", a local brothel who pays lip service to the Church's rule over Venice and serve as allies and a spy network for the Assassins.
- Assassin's Creed: Freedom Cry: Bastienne Josephe is the local madam who runs an informant network comprised of her prostitutes on behalf of the Maroon rebellion.
- In Dishonored, Emily Kaldwin, daughter of the murdered previous Empress Jessamine and thus the presumptive Empress, has been kidnapped by Hiram Burrows and held in The Golden Cat, a brothel managed by Madam Prudence.
- In Final Fantasy XIV, Yotsuyu was hired as an expendable spy asset for the Doman Liberation Front. She was supposed to use her beauty to seduce Garlean customers and get information out of them that could be of use to the Resistance. But given that she was sold into sex slavery and is a Boomerang Bigot who hates Doma, she quickly grows frustrated with her position and reveals her hatred before Zenos, who was indifferent to her advances. Seeing this, he instates her as the acting viceroy of Doma, allowing her to crush the nation she hates so much under heel.
- In Heavy Rain, the first time we see Scott Shelby is when he pays a prostitute so he can ask her about the Origami Killer.
- Saints Row: The Third: In order to eliminate the Saints, Viola and Kiki DeWynter hire a bunch of prostitutes and anonymously organize a party at the Saints' penthouse, assisted by the fact that the Saints have a steady stream of prostitutes and strippers going in and out of the penthouse at all times already. Being sexually eager, the male Saints don't realize the prostitutes are here to assassinate them until the Boss narrowly stops one of them from shooting Pierce with his own gun whilst straddling his lap. At this, the other prostitutes pull out really big firearms from... somewhere, and start shooting the building up. Ultimately, though, the Saints win the firefight, because however well-armed the prostitutes are, they're still wearing Stripperiffic clothes instead of tactical body armour, which means they can be shot dead as effortlessly as any other enemy. In the aftermath, the DeWynters are read the riot act by their erstwhile allies:
Killbane: HOOKER ASSASSINS?!
Viola: They came highly recommended!
Matt Miller: Ladies, it was a pretty shit plan.
