Dirty Harriet

Well, when you're wearing that, I definitely do feel lucky.

The baseline Dirty Harriet scenario is when a female law enforcement officer goes undercover in a role only a woman is expected to take, like stripper or prostitute. This allows for the natural tensions of undercover work, and of course also provides a reason for her to wear little clothing. Building on this, there are a number of other possible variations on the trope. The woman might not be proper law enforcement (perhaps she's a private detective, for instance), or the role might not be immediately connected to sex work (though still require her to wear sexy clothes). Or, it might actually be a male officer who is Disguised in Drag for similar purposes: perhaps the job is simply deemed too dangerous for a woman. In the latter case, unless it's played for laughs, it's likely that the guy looks good enough in drag to pass convincingly as a woman, at least at first glance. Or possibly, he is deliberately impersonating another Crossdresser, or a Transgender woman.

Note that while this does happen in reality, it's very controversial, and legally and morally delicate. It has a very high chance of going spectacularly wrong and can easily turn into the sort of situation where a would-be arrestee is suing the city or the state or the feds for entrapment or worse. The real-life prostitution stings shown on various cop documentaries usually entail the undercover officer doing just the absolute minimum to make it absolutely clear that the client is really buying sex, and once money has changed hands excuse herself while her colleagues (who have been monitoring the situation from the next room or a parked car) storm in and make the arrest. This is also a uniquely American trope, given the varying legality of prostitution across the world.

This also appears in Spy Fiction. Serial Killer Baiting often involves this trope. See also Fair Cop. Almost never falls victim to Can Always Spot a Cop.

The term has also been used to describe female police officers depicted in film, TV, and literature as being just as deadly as their male counterparts (or, specifically, Clint Eastwood's Dirty Harry character)^note A mid-1980s TV series titled Lady Blue, about a deadly female cop, was in fact promoted by the network as being a "Dirty Harriet" series. But that is not what this trope is about.

See Stripper/Cop Confusion for a humorous inversion of the trope.

If someone disguises themselves as a prostitute to commit different crimes, see Shady Lady of the Night.

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Examples:

Anime & Manga

• The title Space Cop of Birdy the Mighty: Decode does this in episode 5 to figure out who is behind a terrorist attack.
• In Cat's Eye, police officer Mitsuko Asatani was once disguised as a bartender wearing a Playboy Bunny suit.
• Code Geass: In season two, Action Girl Kallen is forced to work as a bunny-girl at an upscale casino as part of the Black Knights' plan to recover the amnesiac Lelouch/Zero. She's almost dragged off for a "bunny hunt", but Lelouch intervenes.
• Cop Craft: Tilarna is sent to infiltrate a "dating club" in episode 7 and winds up being paired with an up-and-coming politician. She is less than pleased at how long the other cops take to bust in.
• Minnie May in Gunsmith Cats filled this role as she had experience as the real thing, and easily passed the "audition" because of it.
• In Monster, Nina resorts to this in order to find her brother.
• In Ninja Slayer, supporting protagonist Nancy Lee one time masquerades as a prostitute to try to gain easy access inside a Syndicate facility. It works a little too well, in fact.
• Episode 15 of Samurai Champloo.
• Trinity Blood has a fleeting scene where Catholic nun Esther is used as a bait to catch a criminal. Blatant fanservice, that.

Comic Books

• In Age of Apocalypse, Husk went undercover as a human prostitute to get into the slave camp Illyana was kept in.
• Birds of Prey: One of Black Canary's conditions for joining Oracle's operation was that she would never have to impersonate a stripper. (The other was never having to use a computer.)
• In the G.I. Joe: Cobra miniseries, Jinx went undercover at a strip club in order to make contact with Chuckles.
• League of Extraordinary Gentlemen: Mina Murray goes undercover as a Parisian demi-mondaine to lure out Mr. Hyde.
• Lucy does this in her introductory issue of Marville.
• Lt. Bliss poses as a hooker in The Maze Agency Annual story that was a homage to The Spirit.
• Robyn Hood: Robyn goes undercover as High-Class Call Girl to bring down a dirty politician in #1 of her ongoing series.
• Ruse has a story in which Emma goes undercover as a Streetwalker to find a Jack the Ripper-type killer.
• Sin City: Silent Night has an inversion. Marv goes undercover as a "customer" in order to infiltrate a sex ring and rescue a little girl.
• Valérian: In order to approach two Space Pirates, Laureline dresses up as a call girl.

Fan Works

• Back For Good: When Emirati U.Z.Z. agent Tushika Hoshino is first introduced in Chapter 7, she's working undercover as a stripper at Cavalli Club in order to keep a look-out for human traffickers in the act.

Film — Animated

• Catwoman poses as a stripper in order to get close to Rough Cut in DC Showcase: Catwoman.

Film — Live-Action

• The Baron encounters the crossdressing variant immediately after the opening credits of The Candy Tangerine Man. He crushes the man's Johnson in order to escape.
• Pam Grier's character in Coffy goes undercover as a call girl for a local drug dealer/pimp in order to infiltrate the criminal underworld, although she's a vigilante, not a police officer.
• Confidentially Yours: Amateur Sleuth Barbara passes herself off as a prostitute so she can investigate the seedy nightclub Red Angel without looking conspicuous. She's quickly figured out though, because she guessed the nightclub's owner/pimp's gender wrong.
• District 13: Ultimatum opens with one of the leads going undercover as a dancing girl in order to stage a major sting against a series of crime bosses. The twist? Both the movie's leads are male. But it must be said that Cyril Raffaelli looks stunning in a dress.
• In the Pam Grier movie Foxy Brown the protagonist goes undercover as a prostitute to exact revenge on the local crime lords, just as in its Spiritual Predecessor Coffy.
• Jack the Ripper (1976): After Inspector Selby starts to bear the brunt of the press's criticism for failing to catch the Ripper, his girlfriend Cynthia decides to go undercover as a streetwalker in an attempt to catch the Ripper.
• In Khalnayak Ganga (Madhuri Dixit) goes undercover as a dancer to try to catch Ballu (Sanjay Dutt) and save her boyfriend's reputation. She gets in waaay over her head, however, when Ballu develops feelings for her.
• In Maniac Cop, Theresa Mallory, Officer Forrest's girlfriend, works for Vice Squad, and she is seen working undercover as a prostitute before Cordell attacks her.
• In Miss Congeniality the titular character is an FBI agent that infiltrates the Miss United States pageant to find out who's threatening it.
• WPC Josie March poses as a prostitute in an attempt to lure the serial killer in Night After Night After Night.
• Rambo: First Blood Part II. Co poses as a prostitute to get inside the prison camp where Rambo is held.
• In Sabotage (2014), Lizzy infiltrates the cartel safe house as a party girl.
• Averted in Stir Crazy. When a paralegal goes undercover at a strip joint, she does so as a waitress.
• In South Central, Bobby, Loco, and another gang member are cruising down the road when Loco spots a prostitute. Bobby, who's trying to lay low after killing a drug dealer named Genie Lamp, suspects there might be trouble and urges them to drive away, but the other two bring her into their car anyways. Loco tries to flirt with her by offering her drugs, at which point the prostitute reveals that she's actually an undercover officer, leading to their arrests.
• The Roger Corman sexploitation movie Stripped to Kill and the inevitable sequel. A Serial Killer is killing strippers, so a policewoman becomes a stripper to lure him out.
• Tomcats: When Michael first meets Natalie, he's a bit surprised that she's a prostitute. He's even more surprised when he gets his face slammed against a wall, put in handcuffs, and finds out she's really a cop.
• Played with in True Lies. Helen Tasker thinks she is doing this, but it's actually a setup by her husband Harry, who really is a secret agent, to give her the excitement he thinks she's looking for. Before he can reveal everything, actual terrorists kidnap them both and things escalate from there.
• Undercover Heat. Dirty Harriet police officer Cindy Hannen (Athena Massey) goes undercover in a high-class whorehouse to catch a murderer. She discovers the fake clients set up for her cannot be relied upon and when faced with real tricks decides to sew her "Wild oats" and enjoy a sexual adventure as a real prostitute, transforming from tomboy into Fair Cop via a Girliness Upgrade, essentially Becoming the Mask. Also played with when she does a roleplay as a Dominatrix cop for one of her unwitting clients and indulges in A Threesome Is Hot with an attractive married couple.
• Walking Vengeance: Male non-cop version, Aurora has a habit of hiring male prostitutes; assassin Gabriel intercepts her call and pretends to be the prostitute.
• In The Warriors, Ajax ends up getting arrested when he attempts to rape one of these. She then proceeds to cuff him to a park bench and call for back-up.
• In X-Men: First Class, in order to infiltrate a Hellfire Club private party, Moira MacTaggert strips down to her undergarments and pretends to be one of the call-girls. Done fairly well as it's shown that she's not all that comfortable with it and is acutely aware of how vulnerable she is.

Literature

• In one Stuart Macbride's Aberdeen detective novels the fanservice aspect is averted. The officers posing as streetwalkers are plain and unattractive because an attractive street-corner prostitute would make people suspicious.
• In Assassins of Gor Elizabeth Cardwell goes undercover in Ar as a slave girl. Of course, this being Gor and she being female, she immediately starts heading in the direction of Becoming the Mask.
• Dexter's sister Deb did this at the start of the first book when she was working in vice. The tone of the books is much more negative than that of the show and Dexter as the narrator spends some time on how incredibly unattractive Deb, a beautiful woman, managed to make herself look in such skimpy clothing. She wasn't trying, either; she has no fashion sense. By contrast, Deb in the show has a perfectly good fashion sense.
• Discworld: Nobby Nobbs. Yes, he's a man, or at least male. It's complex.^note Extremely complex. For the sake of simplicity, Nobby is one of the few individuals in the world who has to carry around a card saying he's an actual human. In fact, Nobby's looks are so astounding that a footnote made sure to point out that although narrative law would normally demand an Attractive Bent-Gender moment, the trope withered and died in the face of Nobby Nobbs.
  • Even better: in one instance, his partner for that operation is the very attractive Sgt. Angua, a werewolf. Nobby can't imagine she'd be the bait (and feels a lot safer with her as backup rather than the other way around).
• In The Golgotha Series, Kate is a detective who goes undercover as a prostitute in Golgotha's brothel.
• Holly Lisle's Last Girl Dancing is a textbook example of this trope: the protagonist is a female cop who goes undercover as a stripper to find a serial killer.
• In Monster Hunter International, Heather in Alpha is mentioned to have worked undercover in such a position as a city police officer to bust a drug ring before returning to her hometown in Michigan and even jokes about it a bit to Harbinger.
  "The one with all her teeth? That's the undercover cop."
• In Shatterglass, part of Tamora Pierce's The Circle Opens Quartet, a serial killer stalks the female yaskedasi, or members of the entertainment class. Quite a few police officers (of both genders, but mostly women) go undercover as yaskedasi, but this is played straight when someone else comments that the grimly staring few who can't dance, juggle, or sing really stick out.

Live-Action TV

• On 21 Jump Street, Judy joined the Jump Street program because it was the only way she'd be able to get any other type of assignment. Of course, this didn't mean that she didn't still get just such an assignment occasionally.
• The pilot episode of Airwolf features the F.I.R.M. getting an American agent employed as a belly dancer in Libya. Her cover is blown and she is killed later. They then decide to send in another belly dancer, who gets kidnapped by the evil Dr. Moffett, tortured, and ends up dying from dehydration in the Sahara. As the second agent is a Love Interest of Stringfellow Hawke, her death gives him a personal stake in the mission to recover Airwolf.
• Angel: In the original plan for the second episode, Kate Lockley was to be introduced as a police officer infiltrating a prostitution ring. In the version that made it to air, she was investigating disappearances from (or hanging out at) a popular singles bar. She would go on to become the Fair Cop love interest and occasional antagonist for Angel Investigations for the first 2 seasons.
• In the reality series Armed And Famous, both female celebrities (Trish Stratus and LaToya Jackson) went undercover during a prostitution sting. In contrast to typical portrayals, this wasn't played for Fanservice, and both were dressed very casually.
• Ashes to Ashes (2008): Alex Drake arrives in 1981 dressed as a prostitute. Later, in 1.05, she pretends to be one again - unfortunately for her, she isn't the mark's type.
• The Bill: Cathy Bradford, but there are other examples.
• One episode of Blue Bloods has Jackie going undercover to catch a killer with a predilection for webgirls.
• Cagney & Lacey: In episode 1 of season 1, no less, leading to Lacey's classic snark as she and Cagney stand on a streetcorner in extravagant hooker outfits:
  Det. Lacey: They call these plain clothes?
• Charlie's Angels:
  • The standard operating procedure of the Angels is to go undercover. Some of these assignments involve posing as prostitutes, exotic dancers, or in massage parlours, which gives many opportunities for Fanservice.
  • In the first season finale, "Blue Angels", all three angels and Bosley go undercover in different places, and two of the assignments qualify as this trope: Jill impersonates a masseuese in a massage parlor (with Bosley as the manager). Sabrina goes undercover in the LAPD as a Phoenix vice detective, and is immediately ordered to impersonate a prostitute in order to infiltrate a different massage parlor.
• Cracker, series 3 episode "Brotherly Love": Penhaligon dresses as a prostitute hoping to lure a man believed to be murdering prostitutes. There's extra tension in the put-on because Penhaligon was still recovering from being raped by a colleague.
• In the Season 13 finale of CSI, Morgan goes undercover as a prostitute to try to find a serial killer. This entails her removing her dress, although we see nothing below the shoulders... and later almost ending up a victim of said killer herself.
• In Death Valley, Carla goes undercover as a Sex-For-Blood vampire prostitute.
• Decoy: Casey's first assignment requires her to go undercover at a carnival. The only job she can find is dancing in a harem outfit with three other girls outside a tent.
  Barker: From the far-off lands of mystic Persia, from the palace of a thousand delights, come these exotic enchantresses of the East, whose sensuous and curvaceous movements have never before been seen by anyone outside the closely-guarded walls of the Raja's harem.
• Dexter
  • When we first meet Deb, she's working in the vice squad (that would be Miami Vice), assigned to a prostitution sting operation, and is desperate to get assigned out of it. Especially when she ends up helping out at a murder scene... still in her disguise.
  • In season 3, Angel's new girlfriend is also undercover as a prostitute. Which he learns when he tries to hire her.
  • Season 5:
    • Officer Cira Manzon is chosen to impersonate a club thot as part of a sting to apprehend a dangerous gang leader.
    • Maria LaGuerta agrees to be part of a sting to catch a Dirty Cop by suggesting a sexual liason. This creates tension with her husband Batista since he mistakes the whole thing for an affair she's having with an IAD detective.
• Father Brown: In "The Crimson Feather", Bunty goes undercover as a burlesque dancer.
• Hill Street Blues: In the season 5 episode "Davenport in a Storm", a number of female officers and detectives pose as streetwalkers to catch a serial killer targeting prostitutes. This is not played for fanservice (it's winter and even the street walkers wear covering clothes) but it is emphasized that the operation is dangerous; in fact, Det. Patsy Mayo asks to ride as backup rather than pose as a prostitute because of the risk.
• In the first season of the 1980s cop show Hunter (1984), Hunter's partner Dee Dee McCall poses as a streetwalker quite often (from the very first moment we see her, actually), usually to gather information rather than as a part of a sting operation. In later seasons she doesn't do it as often, but it still happens. Somewhat unusually, this is not played for fanservice, at least not in the case of McCall herself - she tends to wear considerably more clothes than her supposed "colleagues".
• Ekaterina "Katia" Vorobyova in The Interns. To collect materials about prostitutes for new article, she herself pretended to be prostitute (they would only trust one of them). She took precautions in case someone would actually try to force her into sex, taking shocker, pepper spray and switchblade.
• JAG: Mac goes undercover in season 5 as a Chief Petty Officer trying infiltrate a Wicca group, including getting herself sky-clad.
• Law & Order: Criminal Intent: Detective Stevens poses as a High-Class Call Girl in order to get an interview with the madam of an exclusive escort service in "Gods & Insects". The squad room breaks into applause when she returns still in her outfit.
• Law & Order: SVU: Happens often with Olivia Benson.
• In Lois & Clark she did this as a showgirl to get inside info on a crime ring. She was pretty good at it. Lex Luthor was highly amused when she appeared on stage. Meanwhile, Clark, who was working the same story undercover, fretted a lot and didn't have that much remorse fingering Lois to the female mob boss he's ingratiated himself with when they are caught sneaking around in order to preserve his cover.
• One episode of Legends has Crystal briefly going undercover as a stripper.
• Lost has a Show Within a Show called Exposé about a group of secret agents undercover as strippers.
• Miami Vice: Practically the only thing Gina and Trudy ever seem to do is go undercover as prostitutes. At least, this tends to be the only time they get the spotlight; otherwise they are mostly support for Crockett and Tubbs.
• Miss Fisher's Murder Mysteries: Phryne goes undercover as a Spanish fan dancer at a gentleman's club in "Murder Most Scandalous".
• NCIS: In "High Tide", Bishop has to go undercover as an escort to help bust a drug ring. She cleans up so well that she is rated a "hard ten" by the perps.
• NYPD Blue
  • In one episode Det. Kirkendall goes undercover as a call girl to get evidence against a suspected murderer. The operation is portrayed as unusual and risky (since there is good reason to suspect that her customer will try to kill her), is not undertaken lightly, and is not played for Fanservice.
  • Detective McDowell impersonates a prostitute to get close to a drug dealer who is surrounded by armed henchmen. It's not an extended undercover operation — as soon as she is in the same room as the dealer, her colleagues storm the place. In the resulting scuffle, her top (that didn't cover too much to start with) gets torn open, providing a gratuitous Lingerie Scene.
• The 1985 TV movie Operation Julie opens with a roomful of undercover police watching film footage of them pretending to be hippies to investigate drug selling at a pop festival. They especially appreciate the shots of their female colleagues walking around topless.
• Pepper Anderson in the 70's series Police Woman (played by Angie Dickinson) and her colleagues go undercover in almost every episode. Since she is the only woman in her squad, some of her assignments fit this trope. These usually involve wearing quite revealing clothing, which is played for fanservice. In at least one instance her cover is blown when she refuses to have actual sex with a client.
• Happens all the time on Reno 911!, with a few different outcomes.
  • Deputy Weigel, the squad Butt-Monkey, scares off the johns.
  • Deputy Williams winds up knowing her young client from her old neighborhood and starts off giving him an angry lecture, before commenting on how well he's grown up and shutting off the recording equipment.
  • At one point, the other deputies roust the prostitute hangout, only to find Deputy (Jim) Dangle among them, dressed as one. He tries to invoke the trope and convince them that he's undercover, but the others slowly catch on to the fact he is moonlighting as a gay prostitute as they leave.
  Dep. Junior: Doesn't he have Fridays off?
• In Robin Hood Kate pretends to be a drunken tavern wench in order to distract one of the outlaws' targets, a job that includes a low-cut dress and lots of makeup. She hooks up with Robin in the very next episode. Hmmm...
• Played with in The Shield:
  • A detective has to go undercover to catch a mob that's beating up prostitutes. Male prostitutes. Shane is very upset when he's forced into the role.
  • Shane has no luck with this kind of thing. In another episode, the Strike Team had to find out which stripper at a club was luring johns into the alley and then robbing them with her boyfriend. When Vic tries it, he gets a blow job. When Shane tries it, he gets a tire iron to the head.
• Lois Lane in Smallville, although technically not as a cop but as a reporter. Not that anyone cared what her motivation was.
• The first episode of Southland briefly features a female vice cop undercover as a Streetwalker.
• Starsky & Hutch: Starsky's ex-girlfriend turns out to have been undercover as a stripper in "Lady Blue".
• Star Trek: The Next Generation. In "Preemptive Strike" Ensign Ro goes undercover to infiltrate a Maquis resistance group. She passes on her information to Captain Picard by meeting him in a bar, where she tells him to pretend he's buying her sexual services. This adds a level of awkwardness to their interaction (while Ro shares some Belligerent Sexual Tension with Commander Riker, she's never had any with Picard whom she regards more as a stern Parental Substitute). When they meet a second time, Ro has come to identify with the Maquis, so this trope gives Ro's actions as a spy a sleazy feel that doesn't make her feel any better about what she's doing.
• Star Trek: Deep Space Nine. On a couple of occasions Major Kira uses these tactics to infiltrate a Cardassian-controlled area, posing as a prostitute in "The Homecoming" and a comfort girl in "Wrongs Darker Than Death or Night".
• Third Watch: Maritza Cruz, the tough-as-nails female cop (played by Tia Texada). The very first time we see her, working on a prostitution sting, she's wearing "six-inch heels with a postage stamp of polyester stuck up my ass."
• T.J. Hooker:
  • One episode seen Officer Stacy Sheridan going undercover as a prostitute, with her partner Officer Corrigan acting the part of her pimp.
  • In "Hollywood Starr," Detective Dani Starr (Sharon Stone) puts on her "flashiest streetwalking outfit" for a stakeout on Hollywood Boulevard.
• Trace: Fair Cop Oksana Amelina is used to work undercover as prostitute, stripper or simply seductive woman in nightclubs.
• Treadstone. In "The Paradox Andropov", Sooyun gets past the doorman at a nightclub and a security guard outside the VIP booth by pretending to be a high-class prostitute trawling for customers among The Mafiya in the VIP booth; it helps that she can actually speak Russian thanks to her conditioning, thereby gaining the Big Bad's attention.
• One episode of Two and a Half Men has Charlie getting busted by one of these. This clues him in that his sexual life is getting out of hand (not that sleeping with many women is news to him, but in this episode, he was so unhinged that he literally broke his balls after sleeping with six or seven girls in the same day).
• Detective Shraeger in The Unusuals starts out in vice, dressed as a hooker. She's soon transferred to homicide, though.
• White Collar has FBI agent Diana undercover as a prostitute in an episode of the second season as part of an operation to bring down a corrupt politician.
• Without a Trace:
  • In her first episode, Elena poses as a call girl to get information from a suspect. In "Candy", she goes undercover as a stripper.
  • In another episode, Martin and Danny are interrogating a prostitute who was the last person seen with a missing judge when she mutters under her breath, "I'm a cop, so make this look good." They promptly begin yelling at her and roughing her up to maintain the facade of her being uncooperative.
• The Wire: Played With. Kima goes undercover as a stripper, but not to catch some unsuspecting john. The Major Crimes unit is investigating a drug kingpin using the owner of his strip club, Orlando, to implicate key members of the organization. Kima is going along on the ride mainly as an eyeball witness. Unfortunately, Orlando's bosses already knew he was a snitch and ordered a hit on him. Orlando is shot and killed while Kima is shot, but narrowly survives.

Tabletop Games

• The New World of Darkness sourcebook Tales from the 13th Precinct features a vice cop who gets sent on this type of assignment by default.

Video Games

• Anachronox: Stiletto Anyways makes her first appearance as a stripper before it turns out she's undercover as an assassin, killing three mobsters halfway through the performance. Afterwards, the bar owner thinks it's a great act and wants to hire her full-time.
• Dead or Alive: Christie went undercover as an erotic dancer in order to get close enough to assassinate her target in her Dead or Alive 4 ending.
• In Deus Ex: Human Revolution, one of Jensen's old partners will be undercover as a prostitute.
• In Final Fantasy VII Tifa Lockhart does so to get information from Don Corneo, then Cloud and Aerith do it too to free Tifa.
• In Grand Theft Auto V, it's possible to get caught in a sting operation when picking up prostitutes.
• A T-rated variation in Jak II: Renegade: The Underground is allied with local crime lord Krew, but since Torn doesn't trust him, he sends Tess to work at his saloon as a barmaid (and nothing else) to pass his secrets along.
• In Neverwinter Nights 2, a supposed high class courtesan involved in the hunt for the King of Shadows is revealed to actually be a member of the Neverwinter Nine in a sting operation.
• Inverted in Lula 3D: Lula is a porn producer and prostitute who goes undercover at a strip bar to track down kidnapped actresses.
• Played with by Mass Effect. One of the early Citadel missions involves a young woman working in Chora's Den, a sleazy, mobster-owned strip club in the Wards (The heavily populated, urban sections of the Citdael). She is working at the club to pass on information to the local police, and she very specifically points out that she only serves drinks on the bar. Of course, she then complains that she could be earning more money by dancing.....
• Mother 3: While she wasn't necessarily hired as a stripper, Kumatora worked as a waitress at a night club in order to locate and rescue the amnesiac Duster.

Visual Novel

• Shall We Date?: Ninja Shadow has the Sweet Polly Oliver protagonist, Saori, do this once in a while as a part of her missions: her companions think she's a girly-looking boy and often need her to get info and fulfill missions in the Red Light District. Toru Nakagawa's route begins with Saori pulling one of these missions, then meeting Toru and having him fall in Love at First Sight with her...

Web Comics

• Parodied in the Gurren Lagann fan webcomic DOUBLE K, in which Simon is sent in as the Dirty Harriet. Repeatedly.
• In Too Much Information (2005), Officer Friendly ends up undercover as a streetwalker, which both provides her with an excellent opportunity to get closer to Ace - by stating that it would really help her cover if she was seen getting into the sleek sports-car of an attractive young man - and provides Betty and Veronica with a good opportunity to see Ace drive around with a scantily-clad girl in his car.
• Undercover cops posing as prostitutes became the topic of conversation in Leftover Soup when ex-cop Cheryl is asked if she's ever done undercover work. She says she turned down the offer out of concern for her Identical Twin sister, and brings up the issue of how easily it can cross the line into entrapment—"you can't actually offer it...you have to just wear a short skirt and imply things." Jamie then asked if an undercover cop posing as a customer ever tried fake-soliciting an undercover cop posing as a prostitute, and how it turned out, prompting this response: "Last I heard, they're married with five kids." (And a comment from the writer: "Admit it, you'd watch that movie.")

Western Animation

• Arcane: Vi has Caitlyn pretend she works at the brothel in order to get info from people, saying it ought to be easy given she's a Fair Cop. Caitlyn is mortified at the idea, but goes along with it. It's implied Vi did that just to get Caitlyn out of the way while also annoying her, and Vi is visibly (but pleasantly) surprised later when she spots Caitlyn seemingly successfully chatting up with a female client.
• Patrol 03: Carmen once disguises herself as what is clearly meant to be a prostitute, as she wears makeup, goes to a male character in a truck parked in a bad neighborhood and entices him out with sexy talk.
• South Park:
  • Parodied when a (male) police detective goes undercover as a (female) streetwalker to bust a prostitution ring... and gets a bit too deep into the role. To the point of marrying the (also male) leader of the ring and only revealing that he's a cop after the honeymoon.
  • Cartman goes undercover as a hooker when deputized by Barbrady so he can learn to read.

Real Life

• US trucking companies that have policies against their truckers letting anyone into their cabs (especially prostitutes) have been known to hire undercover "lot lizards". These girls will target truckers from the company that hires them, and ask if they want a "bedtime story". If the trucker lets them into the cab, they get fired.

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