Somebody passing for the other gender is a common trope in comedy, all the way back to Shakespeare. However, it usually works only if the actor in question actually makes an effort to look and behave like a member of the opposite sex, otherwise the audience's Willing Suspension of Disbelief is broken and instead of being about, say, a man trying to pass as a woman, the work becomes about how a group of morons didn't realize they were trying to pick up a drag queen. Occasionally it works, if applied side by side with Rule of Funny.
- In Fist of the North Star, Kenshiro once confronted a gang of Ken-Oh's henchmen in a bar, one of them disguised himself as a nanny barkeeper, it doesn't take that much of efforts discover the disguise as he didn't shave properly.
"The next time you want to play crossdressing, shave properly. No real woman in the world would have a beard."
- Magical Shopping Arcade Abenobashi's Crossdresser "Ms." Aki. is never outed, but is rather obvious — so much so that it seems the rest of the cast is aware of it and just treats him/her as a lovable eccentric.
- One Piece:
- All the crossdressers from the series are incredibly ugly and clearly don't shave, though they still behave much like women. The only exception so far is the secondary character Izou: The only thing that gives away his sex is his lack of cleavage.
- Another example is Igaram, who disguised himself as Vivi to serve as a decoy twice. Problem is; he's a 48-year-old man with broad shoulders, while Vivi is a slim teenage girl. The second attempt didn't fool anyone, but it did leave the Alabasta citizens distracted long enough to allow Vivi to properly say goodbye to the Straw Hats.
- JoJo's Bizarre Adventure gives us Joseph's famous attempt at infiltrating the Nazi lab in Mexico. The guards aren't fooled by an instant: no matter how hard he tries to act girly (and he tries a bit too hard for his own good), he sure as hell can't look the part.
- In Penguin Revolution, the talents and managers of Peacock are required to dress in drag for a publicity event. Most of the actors pull it off remarkably well, but Kaneda, one of the managers, just looks like a man in a dress.
- Mad Bull 34 takes the cake, here. The "Mad Bull" himself, an eight-foot-tall muscular behemoth of a police officer with a full beard and mustache, goes undercover as a nun and as a female prostitute. He somehow expects this disguise to work.
- Sven◊ in the anime of Black Cat refused to allow Eve to serve as a Dirty Harriet in order to lure out a Serial Killer who targets women, so he does so himself and doesn't even bother shaving his beard.
- In Laughing Under the Clouds Tenka disguises himself as a woman so he can spy on Chutaro. Since it's played for laughs it looks just way over the top and nobody's buying the disguise, anyway.
- In Gugure! Kokkuri-san, Shigaraki's poor attempts to disguise himself as Kohina◊ to appeal to her Stalker with a Crush Inugami fool no one due to his muscular build and hairy legs, and it just disgusts Inugami more than anything else.
Shigaraki: (still in his Kohina disguise) The dog seemed down, so I tried being nice to him, but he cried and ran away.
Kokkuri: In that situation, I'd run, too.
- Played with in Family Compo where Masahiko asks his aunt and uncle/adopted parents (who are transgender) to come to his school entry dressed as their biological sex. The result is both of them appearing visibly uncomfortable in Incredibly Conspicuous Drag, when in fact Recursive Crossdressing is what's really going on.
- The boys of Ouran High School Host Club use this in order to keep Haruhi from transferring to the Lobelia Girls' Academy.
- Cowboy Bebop has an incredibly masculine drag queen that shows up in both Jupiter Jazz episodes. He tries to hit on Edward until being informed that Ed is a girl.
- The Beagle Boys in Donald Duck comics. They still wear their masks, and don't shave.
- Aversion in a Don Martin cartoon for MAD: Men looking for an escaped convict at a train station see a hairy-armed, tattooed, stubble-faced person in a dress walk by. One of them pulls off the person's wig and they jump on the presumed escaped convict... but let her go with shamefaced apologies.
- Jokey Smurf in The Smurfs one-page gag in "Romeo And Smurfette", who disguises himself as Smurfette (not perfectly) in order to fool a Smurf into a Prank Date. Needless to say, the Smurf was neither fooled nor amused.
- The National Lampoon had a comic-book style ad for magazine subscriptions with two clearly middle-aged men (one had a moustache, the other stubble and a cigar) dressed like housewives at a supermarket. They addressed each other with female names, the employees regarded them as women, then the last panel had the police turn up and haul them off. None of this was explained in the least.
- At the climax of Mulan several of Mulan's male comrades join her in infiltrating the palace by disguising themselves as concubines◊. Yao doesn't even bother shaving his beard and one of Ling's breasts appears to be crooked, but Chien-Po is the most passable of the three and simply looks like a very fat woman. Amazingly the disguises mostly work on some guards.
Guard 1: Concubines?Guard 2: Ugly concubines.
- Open Season: In the "Scared Silly" special, Boog has to play a female Wumpus monster, to lure out the male species.
- As the page quote indicates, the WWII comedy All The Queens Men (allegedly Based on a True Story) completely destroys any possibility of seeming authentic because the actors (including Eddie Izzard) make absolutely no attempt to be believable as women.
- The Birdcage features Albert (Nathan Lane) dressing up in drag to convince a conservative family that he and his gay partner, Armand (Robin Williams), are in fact a normal straight couple to cover for their son, who is getting engaged to the conservative family's daughter. Not only is his drag conspicuous, but Albert and Armand's house is full of tells that they are, in fact, a gay couple. At the end of the movie, the entire conservative family has to dress in drag in order to escape the titular gay nightclub owned by Albert and Armand without being noticed by the press.
- A number of the Carry On films involve Sid James or Bernard Bresslaw (or another similarly unmistakeably masculine cast member) wearing a dress, and the authority figure they're trying to evade falling instantly for him, despite the fact that he's clearly Sid James or Bernard Bresslaw wearing a dress. (The fact that the authority figure was frequently Kenneth Williams may add a bit of subtext to this.)
- Played for Laughs in Gangs of New York when an incredibly obvious transvestite (stubble and all) shows up to a dance where males are paired with females. He, of course, goes to the "female" side.
- Subverted in The Rocky Horror Picture Show. Frank N. Furter doesn't really try to pass off as a woman yet Brad (ASSHOLE!) ends up falling for his seductive charm anyway.
- Averted in Some Like It Hot. Jack Lemmon and Tony Curtis actually walked around the studio lot in drag in order to make sure they could realistically pass for female. The scene were they try using mirrors in the public ladies' room in order to fix their makeup is based on something they actually did while on the lot.
- When asked why his "Josephine" was so much more feminine than Jack Lemmon's "Daphne", Tony Curtis explained that he was so scared to be playing a woman (or a man pretending to be one) that his tightly wound body language could be read as demure and shy, traditionally feminine traits, whereas Lemmon, who was completely unbothered, "ran out of his dressing room screaming like the Queen of the May," kept much more of his masculine body language.
- Sorority Boys is a textbook example. Back to Roger Ebert:
"What is unusual about "Sorority Boys" is how it caves in to the homophobia of the audience by not even trying to make its cross-dressing heroes look like halfway, even one-tenth-of-the-way, plausible girls. They look like college boys wearing cheap wigs and dresses they bought at Goodwill. They usually need a shave. One keeps his retro forward-thrusting sideburns and just combs a couple of locks of his wig forward to "cover" them. They look as feminine as the sailors wearing coconut brassieres in South Pacific."
- In Taking Woodstock, Liev Schrieber plays Vetty von Vilma, a transvestite woman. In the part he's very muscular and has an apparent deep voice, in addition to very visible facial hair.
- There was a short from The Three Stooges where Curly dressed like an Indian maiden and a mountain man fell in love with him. Guess it's been a really long time since he last saw a woman.
- Averted by Dustin Hoffman in Tootsie. He might not be an attractive woman (a fact lampshaded several times in the film) but he at least looks like one. That Oscar nomination was well-deserved.
- The failure — or prime source of comedy, depending on how you look at it - of White Chicks is generally considered to be a combination of this and disturbingly unconvincing makeup.
- In Gentlemen of Fortune, the crooks end up escaping in drag. Not only it's incredibly conspicuous, one of the crooks still tries to hit after girls and tries to use the men's bathroom.
- Averted with Zahara in Bad Education (2004), who makes an effort to adopt feminine mannerisms, hair, and makeup on top of the women's clothing. And then played straight with the real Ignacio, who has stubble and an extremely deep voice.
- Sherlock Holmes: A Game of Shadows had Holmes disguising himself as a woman. Since it was a last minute disguise, it wasn't one of the better ones. But in the dark when the other guys could only glimpse it, it worked.
- Madmartigan in Willow tries this briefly to hide from the husband of a lady he's currently boning. It ends up making said husband grossly infatuated with "Hilda", letting him deliver his immortal line:
Lug: Wanna breed?!
Madmartigan: Tempting but... No!
- And when his disguise is quickly blown by the bad guys, Lug does not take it well...
Lug: Not a woman?!
Lug: NOT A WOMAN?!
Madmartigan: Meet Lug.
- In the martial-arts films Come Drink With Me and its sequel Golden Swallow, the female character Golden Swallow is able to pass as a man simply by wearing men's clothing. The fact that actress Cheng Pei-Pei is an incredibly beautiful woman and makes no attempt to disguise her voice is unnoticed by almost everyone.
- In Just One of the Girls, Chris manages to fool everyone into believing that he's a girl despite his disguise consisting only of him wearing skirts and fluffing up his short hair a bit. Even the guy who constantly bullied him before he donned the disguise doesn't recognize him and even falls for his female guise!
- Mic gets hit on by one in Crocodile Dundee. Being A) a rural Australian who doesn't know anything about crossdressing and B) somewhat drunk, Mic still fails to figure it out until his taxi driver informs him that the "lady" who's flirting with him is really a man. Mic checks... via inappropriate touching.
- Averted/Lampshaded in Adventures of Huckleberry Finn. Huck goes into town disguised as a girl, but a woman he encounters immediately tells he's just a boy in disguise.
- Hilariously played with in the Discworld novel Monstrous Regiment. Blouse takes the guise of a woman and is ridiculously bad at it, to the point where all the washerwomen notice right away but don't say anything because they think it's entertaining. But while the women aren't fooled by his awful, extremely stereotypical act, the male guards buy it completely. The funniest part is when the female soldiers masquerading as male soldiers decide to don women's clothing to also infiltrate enemy lines, they're immediately accused of being this trope, saying that they're obviously male and it's the worst attempt at drag they've ever seen.
- Also in The Truth, when the mountainous brain-damaged villain Mr. Tulip is disguised as a nun. It actually works until he starts swearing; as Sacharissa says, she's known genuinely female nuns who looked just as bad, if not worse.
- Averted and played with in Jingo by Nobby Nobbs, disguised as a harem girl for reasons which arent worth attempting to explain. The local women seem entirely fooled, though. (And if they aren't, well... he's still acting more sympathetic to their personal problems than the actual men in their lives...)
- Dave Barry's Only Travel Guide You Will Ever Need recommends that airline passengers who might fit the profile of a terrorist ("Sex: Male; Age: 15 to 74; Looks Suspicious: Yes") to draw away the attention of security personnel away by wearing a dress and "periodically remarking out loud to nobody in particular: 'I certainly have a lot of body hair, for a woman!'"
- Little Red Riding Hood: A wolf disguises himself as LRRH's grandmother by putting on her cap and robe. LRRH does seem to notice that something is off, but cannot quite put her finger on it, as "granny" gives explanation for all the oddities in her appearence.
- Taken Up to Eleven in Split Infinity, when Stile is assigned an android fencing-instructor that's only programmed to teach women. Not only does it call him "lady", but it refuses to commence any lessons until Stile humors its limited programming and dons a protective bra ... which is his only item of apparel, being otherwise naked like all Proton serfs. Yes, he played this trope and Full-Frontal Assault straight at the same time.
- The Buffalo Brothers in Relativity are a pair of Stupid Crooks. At one point, they need to get a message to the heroes, but they don't want to get caught, so they disguise themselves as old ladies. The disguises weren't very good, and probably wouldn't have worked anyway, but the fact that one of the brothers had a beard just made it beyond obvious.
- Done on purpose in the short-lived series The Ugliest Girl in Town.
- Conan wore pearls, lipstick and a wig to try to pass himself off as Callista Gingrich in Conan.
- There was an episode of Jeeves and Wooster where Wooster goes undercover as a woman for some reason, and later in the episode Jeeves does. It was far-fetched, even compared to the usual events of the series.
- Barney Miller - the detectives were assigned to disguise themselves in drag to catch criminals - Dietrich took to the job with good humor, but never realized he just looked like a big guy in a dress.
- Like many British comedies, Doctor in the House and its sequel series featured many episodes of men dressing as ladies, and never looking believable doing it.
- In "Doctor on the Box" from Doctor in the House, three medical students dress a fourth up as an elderly female patient to sabotage an interview as part of a documentary on the hospital; the fact that he is supposed to be an old woman does not stop him from squeezing the female interviewer's bottom. Chaos ensues when the subjects of the documentary discover the deception and decide to administer an enema, and then the real patient returns.
- The Doctor in Charge episode "Mum's the Word" involves the board members having to choose between Dr. Waring and Dr. Bingham as a junior doctor representative on the board; Dr. Stuart-Clark claims that Waring's mother is a Countess (she is, in fact, a policeman's wife). As she is at the hospital as a patient, the board members decide to meet her, and Stuart-Clark dons a blonde wig, blue eyeshadow, and women's clothing and pretends to be Mrs. Waring while the real Mrs. Waring is kept out of sight. His disguise manages to charm the board members, and Waring gets the position on the board.
- "A Turn for the Nurse" from Doctor on the Go sees Stuart-Clark trying to enter a ringer for a "best nurse" competition so that no-one need find out the prize money doesn't exist; Waring persuades her to drop out of the competition, and when Stuart-Clark finds out and reveals the "prize money" quandary, Waring has to dress up in drag as their entrant. His boss, Professor of Surgery Sir Geoffrey Loftus, recognises Waring immediately, but bites his tongue; meanwhile, rival hospital Highcross board member Sir Edmund Steele takes quite a liking to Waring...
- This was Klinger's main schtick for much of the time on M*A*S*H.
- This is a running gag with a background Drop-In Character on Good Eats.
- The "Pepper Pots" of Monty Python's Flying Circus are very obviously men playing the role of middle-aged or elderly women.
- A Full House episode titled "Fraternity Reunion" centers around Danny and Joey dressing as women in order to sneak their way into a sorority house reunion in order to take back a stuffed fraternity seal that was stolen from them in college. In typical Joey fashion he gets to into character and loses his wig in a limbo contest. Danny makes a mad dash for the seal and is subsequently revealed to the women as also being a man. They're both taken down by the women and are arrested by one of them who turns out to be a cop through some sort of Hollywood Law no doubt.
- There is a Norse story in which Thor must disguise himself as Freya in order to trick the giants and get his hammer back (and yes, the hammer stands in for exactly what you think it does). The giants, who are apparently not all that familiar with human(oid) sexual dimorphism, fall for every one of Loki's excuses about why "Freya" looks so haggard, has such a big appetite and can eat an entire cow, has a beard and can drink so much mead in a single gulp. Everything goes swimmingly until the hammer is brought out to bless the marriage, at which point Thor starts Kicking Ass In All His Finery.
- Santino Marella's appearances as "his twin sister from Italy", Santina.
- In 2003, thanks to a match stipulation, Stephanie McMahon had to engage in Hot Lesbian Action with another woman. Eric Bischoff said he found "the ugliest lesbian in the world" for her, but everyone (except Bischoff) knew the "lesbian" was Rikishi.
- In Memphis in 1987, Jerry Lawler disguised himself as a female fan at ringside so he could get close to and attack Tommy Rich. In his book, Lawler said that outside of a little lipstick, they didn't put any makeup on him for it.
- In the 1980's, Jimmy Valiant got Miss Atlanta Lively, "the toughest hooker in Atlanta", to be his tag team partner for a match. "Miss Atlanta Lively" was future NWA Champion Ronnie Garvin in a blond wig and a padded bra.
- Plump washerwomen take note, this is an absolute requirement for any Dame in any Pantomime! Never leave home without your obvious falsetto voice or bustle. Failure to produce bustle or react with extreme scepticism to cries of "they're behind you!" may lead to revoking of your 12x10 comedy-sized licence.
- The character The Old Snatch in the musical Me and My Dick— there are other cross-dressing roles, but this one is played by a man with a gravelly voice and a beard.
- The original stage version of Hairspray cast gravelly-voiced Harvey Fierstein as the mother, Edna Turnblad. The original movie and movie-musical also have the role played by a man, but they attempt to make the mother somewhat feminine and are not examples.
- It's quite common for modern productions of Iolanthe to have The Fairy Queen played by a man in quite obvious drag, playing off the (modern) Double Entendre of the word "Fairy" to mean "gay."
- In SNK Gals Fighters, Iori Yagami has disguised himself as "Miss X" by wearing a long-skirted Sailor Fuku and a mask (in true sukeban fashion) and insisting he's a girl. Nobody who sees him believes it.
- Done for absurdity in Final Fantasy XIV with Hildebrand Manderville during the 2.3 side storyline. Hildebrand disguised himself as the bride who's described as the "most beautiful in the land" to lure out the thief. Everyone is fooled apart from the player character and another inspector who the player is with (surprisingly so as it is very obviously a decidedly masculine character wearing a dress) until the veil comes off. While the effort failed the distraction was enough for the other inspector to identify the target in question who was magically (and more effectively) disguised as the groom.
- A sidequest in Red Dead Redemption II has the player working for an animal wrangler named Margaret—a mustachioed man who dresses as a woman because he thinks a female animal wrangler will attract a bigger audience.
- A later sidequest has you escorting the artist Charles Châtenay, who has dressed as a woman in an attempt to hide from the multiple enemies he's made. He doesn't even bother to shave his facial hair and his low-cut dress shows off his copious chest hair.
- Rapid Thunder (alias Codename: Albatross) in Mappy is a male corporate spy disguised as the female personal assistant of Nyamco CEO Goro. His whole disguise is literally a wig that isn't on right; he doesn't even affect a voice.
- Happens in The Noob, when Your Name Here, a large man with the Face of a Thug, dresses up in drag for a story arc.
- In Girl Genius the fairly bulky man Ollie dresses up as Judy for a humorous role in the pantomime like Heterodyne shows Master Payne's Circus of Adventure puts on in small towns as they travel. To be fair the real Judy is ripped, but she has a very feminine appearance.
- PlayStation Access: "Rob's mum" is obviously a man in a dress speaking in a shrill voice. His face is always out of shot, but the body shape is a bit of a giveaway.
- In an episode of Bob's Burgers, Bob makes friends with some fairly successful transvestite hookers, who look exactly like men in spandex dresses.
- Hefty Smurf disguises himself as Smurfette (also not perfectly) in The Smurfs episode "Smurfette for a Day" to protect her from a gnome who wants to marry her.
- In the "Black Friday" trilogy of South Park (and also in South Park: The Stick of Truth), Kenny dresses up as a princess... and still wears his parka underneath the whole thing, making it very conspicuous. Everyone just chooses not to question why he wants to be a princess in their game.
- Big Macintosh, a big, bulky, deep-voiced stallion, disguises himself as a Southern Belle named "Orchard Blossom" in the My Little Pony: Friendship Is Magic episode "Brotherhooves Social". It's such a shoddy disguise that it only fools exactly one old stallion who ends up getting a crush on him. Rainbow Dash recognies him instantly, and while she doesn't verbally out him to anyone else that can hear, she turns up the snark and tells him not to expect her to take it easy on him in the competition because he's a stallion. Also notable in that it wasn't even necessary for him to dress up to begin with. It's explained by the judges that the competition has a "loose" definition of what qualifies as a sister (basically, a familial-like bond is all that's required), and they would've allowed him to compete as himself if he just asked. Rainbow is allowed to compete as Scootaloo's sister even though they aren't even related.
Applebloom: This is my... cousin, Orchard Blossom.
Scootaloo: That's Big Mac in a dress.
Rainbow Dash (competing as Scootaloo's honorary sister): "Orchard Blossom", huh? Well, I'm not going to take it easy on you just because you're a stallion.
- The "Wossamatta U" story arc in The Adventures of Rocky and Bullwinkle and Friends (which involved Bullwinkle becoming a star football player for the eponymous school and saving them from financial ruin) climaxed in Boris and Fearless Leader amassing a football team compromised of dangerous and big burly criminals and hooligans in order to take down the undefeated Wossamatta football team. In order to make things more humiliating in Wossamatta's supposedly impending defeat, Boris and Fearless Leader have their team do this. The disguises are terrible; mustaches and beard stubble are visible through the men's disguises, yet no one except Rocky catches on immediately (and thus allow the "girls" to get away with a lot of goals thanks to the team not wanting to hit a girl alongside other dirty tactics) until Rocky points this out to them.
- In an episode of The Flintstones, Betty and Wilma enter a television contest for cooking the best cake, and they win. The prize is a huge amount of money, except that they have to bake the cake on television in the show. Unfortunately, right at the wrong time, Betty and Wilma get the measles and are quarantined. Seeing the prospect of great money slipping away, Barney and Fred "disguise" themselves as women. They successfully maintain their disguises, and successfully bake the cake, but blow it by using "Brand B" flour instead of the advertised brand.