A tried and true script device for guaranteed laughter.
Sometimes this is done for fun, for costume parties,
or out of necessity, e.g., to avoid being recognised or to "blend in"
to otherwise single-sex settings.
More recently, movies and television programs are portraying true
transvestism and transsexuals as
indications of an alternative lifestyle, sometimes for
comedy and also in more serious dramatic situations.
===================================================================
other resources:
www.tg-films.info/films_f/film2263.php [via Wayback Archive]
www.cinemadumeep.com/2011/03/gender-switch-movie-monday.html [via Wayback Archive]
Jean-Louis Ginibre. Ladies or Gentlemen: A Pictorial History of Male Cross-Dressing
in the Movies. New York: Filipacchi, 2005, ISBN 1-933231-04-1
===================================================================
Ang Pagdadalaga ni Maximo Oliveros [The Blossoming of Maximo Oliveros](film, 2005)
Maxi/Maximo (12)(Nathan Lopez) is a self-aware, albeit socially troubled, pre-teen.
His self-awareness is obvious in his choice of clothing, styles usually associated
with his female age-mates. His social trouble comes from his poverty, and the
sometimes shady activities of his family and friends. Amazingly, he turns to a
local policeman for solace, understanding, and love. Most people accept Maxi's
choice of attire, allowing the story to focus on the crime and other misbehaviour
going on around Maxi's neighbourhood in the Philippines.
-------------------------------------------------------------------
Anything for Love [Just One of the Girls] (film, 1993)
Chris/Chrissy Calder (Corey Haim) is object of tormentors, then has to go
to the same school where the tormentors are, so dresses as girl to avoid
them
-------------------------------------------------------------------
The Big Wish (TV film, one of the More Winners series of TV specials,
Australian Children's Television Foundation, 1990)
CW, aka Christopher Walter Pratt (Cameron Nugent) gets seven wishes from
Prince Wilton I (Justin Rosniak), and, like The Monkey's Paw, he doesn't
always get what he thinks he's going to get when he states his wish.
In one, he sees Katy, a girl he's smitten with, walking by, and wishes
he could be her best friend. Prince Wilton grants the wish, and CW
is transformed into Katy's best girlfriend!
-------------------------------------------------------------------
The Boy in the Dress (TV film, 2014)
from the IMDb Plot Summary: "Dennis, a twelve-year-old boy, enjoys
football and fashion. The film shows the reactions of his family and friends
to his eclectic activities." Dennis, it seems, has been mesmerised
by a recent issue of Vogue he has seen at his local newsagent and,
bored with the strictures of school and everyday life, he decides to
try "dressing up". He is encouraged when the Vogue
cover model, Kate Moss (played in the film by Kate Moss!) comes to life
and helps him express himself. From the book by David Walliams (half of
the writing and acting team responsible for the TV show Little
Britain), London: HarperCollins Children's Books, 2008
-------------------------------------------------------------------
Boys Klub (film, 2001)
The misfits gang at Father Sal's Boys Club needs to raise money to
enter their basketball team in a tournament. Ernie (Jarrett Lennon)
remembers reading about two female Swedish tennis players who earned
a lot of money in a short time washing cars. [In a scene that
doesn't make a lot of sense except as the writer's idea of comedy,]
the gang -- Ernie, Country (Patrick Renna), Chief (Andre Barishan),
Papi (Ahmad Stoner) and Mario (Chauncey Leopardi) dress as girls and
try to seduce their customers into letting them wash their cars.
Cops break up the [pathetic] scene and take the boys downtown,
where the Boys Club janitor (who later becomes their coach) comes
to get them out. As they are leaving, the janitor takes the money
they earned and gives it to the nearest cop for his "favorite
charity". Later, as boys (i.e., as themselves), they have
almost no success at all with their car-wash efforts.
-------------------------------------------------------------------
The Butcher Boy (film, 1997)
Francie Brady (Eamonn Owens)
-------------------------------------------------------------------
The Castaway Cowboy (film, 1974)
Booton MacAvoy (Eric Shea)
-------------------------------------------------------------------
The Day of the Locust (film, 1974)
Jackie Earle Haley is Adore Loomis, a boy of about 12 whose mother has
been grooming him to be a child movie star -- a female (or female-looking)
child star, that is. Adore's androgyny is complex and mysterious; you have
to see the film and make up your own mind what's going on.
-------------------------------------------------------------------
The Dress Code [Bruno](film, 1999)
Bruno Battaglia (8)(Alex D. Linz) decides that wearing dresses (among other
eccentricities) expresses a higher spiritual purpose in life.
-------------------------------------------------------------------
Eerie, Indiana (NBC, 1991-1992)
"The Hole in the Head Gang", 1 March 1992
Grungy Bill (Claude Akins) is a ghost whom legend regards as the worst bank robber in
the world, because he failed every attempt to rob the Eerie Bank during his lifetime.
He "enlists" (at gunpoint) Marshall Teller (Omri Katz) to help him finally
succeed in a heist. Realising that Marshall likely would be recognised in his
own local bank, Bill disguises Marshall as a frontier woman, complete with bonnet
and ankle-length dress. Apparently it works: when Marshall walks up to the window
inside the bank, the teller (Archie Hahn) says, "Can I help you, Miss?"
-------------------------------------------------------------------
Eerie, Indiana: The Other Dimension (Fox Kids, 1998)
"Perfect", 1998
Mitchell Taylor (Bill Switzer) and Stanley Hope (Daniel Clark) dress
as girls to infiltrate factory that changes girls into "perfect"
dolls.
-------------------------------------------------------------------
Even Stevens (Disney Channel, 1999-2003)
"Scrub Day", 23 September 2000
Louis Stevens (Shia LaBeouf) wears a long red dress and Veronica Lake blonde
wig to avoid being recognized by "Scrub Master" Larry Beale
(Eric "Ty" Hodges II)(Scrub Day is 7th-grader hazing)
"Secret World of Girls", 20 July 2001
Girls dress Louis (Shia LaBeouf) in a nightie, curlers and makeup
to punish him for "invading" their party
"A Very Scary Story", 19 October 2001
In a Hallowe'en fantasy, Louis (Shia LaBeouf) is partially converted into
his sister Ren (Christy Carlson Romano) when a conversion machine fails to
work properly; he has a dress and Ren's body, but still has his own face;
he feels his own shoulder and torso, realizing it's a female
body, and indicates through facial expressions that he's "creeped
out"
-------------------------------------------------------------------
Everything But the Truth (film, 1956)
Willie Taylor (Tim Hovey) dresses in drag to avoid being recognized and
stopped before he can testify in Washington at a Senate Committee hearing.
[Click here for 1956 publicity still - doesn't look happy, does he?]
-------------------------------------------------------------------
The Facts of Life (NBC, 1979-1988)
"The Beginning of the Beginning", 7 May 1988
Adam Brinkerhoff (Seth Green) dresses as girl, Eve Brinkerhoff, so he can
go to a girls' school.
-------------------------------------------------------------------
Family Matters (ABC, 1989-1997; CBS, 1997-1998)
"Cousin Urkel", 2 November 1990
When Steve Urkel (Jaleel White) moves temporarily to Mississippi, his cousin
Myrtle (Jaleel White) arrives and continues the bizarre tradition of the Urkels,
falling in love with Eddie (Darius McCrary).
-------------------------------------------------------------------
Flight of the Doves (film, 1971)
Finn Dove (7)(Jack Wild) and Derval Dove (7)(Helen Raye) switch roles -
Finn dresses as girl, Derval dresses a boy -- to escape their predatory
uncle who wants their inheritance
-------------------------------------------------------------------
Freaks and Geeks (NBC, 1999-2000)
"Tricks and Treats", 30 October 1999
Bill Haverchuck (Martin Starr) dresses as The Bionic Woman for Hallowe'en
(at one point he "feels himself up"!; hilarious).
-------------------------------------------------------------------
Gabriel and Me (film, 2001)
Jimmy Spud (11)(Sean Landless) wears a feathery dress.
-------------------------------------------------------------------
Growing Pains (ABC, 1985-1992)
"Michaelgate", 6 October 1987
Mike (Kirk Cameron) walks into Carol's (Tracey Gold) bedroom to find his little brother Ben
(Jeremy Miller) in a full-length, blue dress ("It's a gown", Ben corrects him
later). Carol is using Ben as a live model so she can fit the dress and fix the hems. [This is a
standard cliché in films and sitcoms with boys and adolescents and their sisters or mothers; for
example, see Leave it to Beaver ("Wally's Play", 11 June 1960) elsewhere on this page.]
-------------------------------------------------------------------
The Heart is Deceitful Above All Things (film, 2006)
Jeremiah (11)(Cole/Dylan Sprouse)
-------------------------------------------------------------------
Help! I'm a Boy (original title: Verzauberte Emma oder Hilfe, ich bin ein Junge... !) (film, 2002)
Emma (Sarah Hannemann) has a mother who wants her to be the best at everything, and a swim coach who
pushes her to be an Olympic-level swimmer. Emma, however, wants to become a different person, especially
after being hassled by her mean classmate, Mickey (Nick Seldensticker). Unaware of the effect it will
have, Emma repeats a sorcerer's spell while complaining about how Mickey treats her. The next morning,
Emma wakes up as Mickey, and Mickey as Emma. The (mostly predictable) hijinx follow, while they
look for a way to break the spell.
-------------------------------------------------------------------
Huckleberry Finn (various films/tv films)
Huck dresses as a girl to avoid being identified as Huck
while helping Jim escape slavery.
-------------------------------------------------------------------
Ladybugs (film, 1992)
Matthew (Jonathan Brandis) becomes Martha to join the all-girl soccer team
coached by his mothers fiancé, Chester Lee (Rodney Dangerfield).
-------------------------------------------------------------------
Leave it to Beaver (CBS, 1957-1958; ABC, 1958-1963)
"Wally's Play", 11 June 1960
Wally Cleaver (Tony Dow) is asked to play a part in the school play
in "drag". Ward (Hugh Beaumont) explains that there is a long tradition
of men playing women in stage productions, and that he participated in such
hi-jinks in college. Wally is clearly uncomfortable, and the use of vintage,
wild-west dance hall music in the background every time we see the dress
Wally will wear only heightens the hilarity. (Does he go ahead and do it
anyway? No spoilers here!)
-------------------------------------------------------------------
The Little Rascals (film, 1994)
Spanky (Travis Tedford) and Alfalfa (Bug Hall) dress as girls in a
ballet troupe to avoid older tough guys (Butch and Woim).
The "bit" is a remake of the scene in the Our Gang short,
"Rushin' Ballet" (1937) [see below].
-------------------------------------------------------------------
Lockie Leonard (Nine Network [Australian Children's Television Foundation],
2007-2010)
"To Cheat or Not To Cheat", 17 April 2007
Lockie (Sean Keenan) and Egg (Clarence John Ryan) are discussing
whether their families would rather they had been born as girls.
In a fantasy sequence, they both appear dressed as girls and talking
in high-pitched voices like girls would ("I mean, like, there are bras
that fasten in the front", "Like, I know").
-------------------------------------------------------------------
Ma vie en rose [My Life in Pink](film, 1997)
Ludovic (6)(Georges du Fresne) is regarded as a boy by his family and
community, despite the fact that the child believes she is a girl.
-------------------------------------------------------------------
Major Crimes (USA/TNT, debuted 2012)
"Boys Will Be Boys", 15 July 2013
Tanner Buchanan plays Michelle Brand. From the IMDb plot summary:
"A 13 year old child with gender identity issues is killed after
being bullied in a mall bathroom."
-------------------------------------------------------------------
Malcolm in the Middle (Fox, 2000-2006)
"Dewey's Dog", 7 April 2002
Dewey (Erik Per Sullivan) gains control of his brothers, Malcolm (Frankie
Muniz) and Reese (Justin Berfield), as well as Craig (David Anthony Higgins)
by virtue of a huge dog he adopts, and forces them to dress as girls
to humiliate them.
-------------------------------------------------------------------
Meet Me at the Fair (film, 1952)
Doc Tilbee (Dan Duryea Jr) and Enoch Jones (Scatman Crothers) dress up
Tad Bayless (Chet Allen) as a girl so he can avoid being detected by
authorities looking for orphanage runaways.
-------------------------------------------------------------------
Mr Bean's Holiday (film, 2007)
Stepan Dechevsky (Max Baldry) gets separated from his father on the way to
Cannes by train, and Mr Bean (Rowan Atkinson) helps them get reunited.
On the way, Bean meets Sabine (Emma de Caunes), an actress with a car whose
small role in a film is being premiered at Cannes. Authorities have
misconstrued Bean's relationship with Max, and have broadcast their images
nationally as a kidnapping case. To gain entry to Cannes, they have to
disguise themselves, Stepan as a Sabine's sister with bright red hair, and
Bean as Sabine's mother. (Bean minces about on his heels, while Stepan
swaggers, like the boy he is [underneath].)
-------------------------------------------------------------------
My Secret Identity (CTV [Canada], 1988-1991)
"My Other Secret Identity", 9 February 1991
When Andrew Clements (Jerry O'Connell) is unable to land himself a male part
in a movie, he takes on the disguise of a girl so that he can get the female
role and possibly get close enough to kiss the star actress.
-------------------------------------------------------------------
My Summer as a Girl (TV film, 1994)
Desperate for a summer job, a teenage boy (Zach Braff as Tony/Tammy)
decides to masquerade as a girl to land a job as a chambermaid.
[summary from IMDb]
-------------------------------------------------------------------
Nancy Drew and the Hidden Staircase (film, 1939)
Frankie Thomas (Ted Nickerson) is forced to wear women's clothes when
his own are stolen during the night in a spooky mansion.
[see: Jean-Louis Ginibre. Ladies or Gentlemen. New York: Filipacchi, 2005]
-------------------------------------------------------------------
Nancy Drew, Detective (film, 1938)
Frankie Thomas (Ted Nickerson) disguises himself as a female nurse to
gain access to a sanitarium to rescue a dowager.
[see: Jean-Louis Ginibre. Ladies or Gentlemen. New York: Filipacchi, 2005]
-------------------------------------------------------------------
Ned's Declassified School Survival Guide (Nickelodeon, 2004-2997)
"Asking Someone Out & Recycling", 4 March 2006
Thanks to Cookie's (Daniel Curtis Lee) foresight in putting a tracking device in Ned's
Guide (the 'School Survival Guide' of the title), when it goes missing, his GPS display
shows that Ned's beloved book is somewhere in the Girls' bathroom. Moze (Lindsey Shaw)
tries, and fails, to find it, so Ned (Devon Werkheiser) decides he must dress in girls'
clothing and look for it himself. Just before taking the plunge, so to speak, Moze
awkwardly tells Ned, "You look . . . pretty." Ned fiddles with his bra straps,
and replies, "I don't know how you girls wear these things, but the skirt's kinda comfortable.
OK, I'm goin' in."
"Secrets & Car Wash", 8 April 2006
The school car wash is set up as a competition between the girls and the boys. When the boys
notice they're way behind, they decide their strategy is to infiltrate the girls' team and slow
them down. Ned (Devon Werkheiser), Seth (Alex Black) and Coconut Head (Rob Pinkston) don the girls'
t-shirt-and-shorts uniforms and stuff them with fake breasts varying from prominent (Seth's, who is
tallest) to barely noticeable (Coconut Head's, who is shortest). Lipstick and rouge enhance the
planned deception, and they awkwardly speak in high, effeminate voices. Seth and Ned wear
long-haired wigs, while Coconut Head - whose hair already is fairly feminine-looking - simply
adds a red bow.
-------------------------------------------------------------------
Oliver Beene (Fox, 2003-2004)
"Nudie Mag", 6 April 2003
Michael (Taylor Emerson) and Oliver Beene (Grant Rosenmeyer) find a
pornographic magazine in a hatbox in the closet at Michael's house. As
they are looking at it, Michael's mother comes home and Oliver leaves with
the magazine under his shirt. He hides it under his mattress, but his
brother Ted Beene (Andrew Lawrence) finds it and takes it to school, where
it ends up destroyed. It will cost 75¢ to replace it (the show takes place
in 1962), and Joyce (Daveigh Chase) agrees to lend them the money from her
Sunshine Girls collections if they will go door-to-door on the weekend
and collect $10.- for her organization. In the last scene we see Oliver
dressed as a Sunshine Girl, at the front door of a man who pinches his
cheek and calls him "the sweetest, most precious Sunshine Girl in the
whole, wide world" -- as he donates 1¢!
-------------------------------------------------------------------
Our Gang Series (shorts, Hal Roach, 1922-1938; MGM, 1938-1944)
"The Pinch Singer", 4 January 1936
Alfalfa (Carl Switzer) disguises himself as a girl so that he can audition
a second time (having been rejected earlier, singing as himself) for an
upcoming radio contest.
"Night 'n' Gales", 1937
Alfalfa (Carl Switzer), Spanky (George McFarland), Buckwheat (Billie Thomas)
and Porky (Eugene Lee) dress in Darla's nighties to sleep over at the Hood's
house during a storm.
"Rushin' Ballet", 1937
Alfalfa (Carl Switzer) and Spanky (George McFarland) disguise themselves as
ballerinas to escape the notice of Butch (Tommy Bond) and Woim (Sidney
Kibrick).
"The New Pupil", 1940
New girl Sally and veteran Darla team up to humiliate Spanky and Alfalfa for the way the boys
have treated them on Sally's first day at school. They arrange for the whole Gang to hide behind
a hedge in Sally's back yard, while Sally tricks first Spanky, then Alfalfa, to dress as neighborhood
women and join her in a mock tea party. They are indeed humiliated when the Gang 'appears', laughing
like crazy. (The whole scene is more uncomfortable for the viewer than it is amusing.)
"Surprised Parties", 1942
Froggy (Billy Laughlin) dresses as a girl to crash a party that
he doesn't know is a surprise party for him (because he
was born on February 29, and only gets one birthday party
every four years).
-------------------------------------------------------------------
Peck's Bad Boy With the Circus (film, 1938)
Bill Peck (Tommy Kelly) is due at Hilldale Boys' Camp to run in a race, but
his friend Fleurette de Cava (Ann Gillis), the child bareback rider in the
circus, has injured herself, so he agrees to ride in her place -- and in her
clothes. After the disastrous, but hilarious, riding stunt, he has no time to
change his dress as he rushes to the camp for his race, and even more hilarity
follows.
-------------------------------------------------------------------
Ready? OK! (film, 2008)
Joshua Alexander Dowd (11)(Lurie Poston) wants to be cheerleader on all-girl
squad (Catholic school), likes dolls, and when he's supposed to portray his
favorite figure in religious history dresses up as Maria von Trapp --
"she was going to become a nun . . .". Note also Anthony
(about 12)(A.J. Foggiano) at Josh's new "arts" school who, when
Josh asks if he was a wrestler (like Josh was, against his will,
at his old school), says, "I'm a choreographer".
-------------------------------------------------------------------
The Robin Hood Gang [Angels in the Attic](film, 1997)
Brad (Clayton Taylor), Frankie (Steven Losak)
-------------------------------------------------------------------
Saved By the Bell (NBC, 1989-1992)
Many episodes have gender-bending dress-ups for the male characters, especially
Dustin Diamond as Samuel 'Screech' Powers. A few examples follow.
"Screech's Woman", 16 September 1989
Zack (Mark-Paul Gosselaar) convinces Screech (Dustin Diamond) that he can find a girl
who is interested in him, but then Zack has to dress up himself to prove his point.
"Miss Bayside", 27 October 1990
Zack (Mark-Paul Gosselaar) bets Slater (Mario Lopez) that he can get anyone to win
the school's Miss Bayside competition. Slater challenges him by nominating Screech
(Dustin Diamond). The rest is sitcom history (or predictability?).
-------------------------------------------------------------------
She's the Man (film, 2006)
Viola (Amanda Bynes) disguises herself as her brother and goes to his
boarding school.
-------------------------------------------------------------------
Silver Spoons (NBC, 1982-1986; Syndication, 1986-1987)
"The Most Beautiful Girl in the World", 8 January 1983
Rick Stratton (Ricky Schroder) dresses as girl to be Derek Taylor's
(Jason Bateman) date at dance as payback for Derek saving Rick's life.
-------------------------------------------------------------------
The Simpsons (Fox, 1989-present)
"Marge in Chains", 6 May 1993
As Marge is going to prison for shoplifting, Bart (age 10) promises to break her out
"just as soon as I get a cocktail dress and a crowbar." In a fantasy sequence,
we see more of what Bart has in mind: he is seen in a red dress, full make-up and
a blonde wig, dancing with the prison warden, who refers to him (her) as
'Bartina', and admits, "until I met you, I was the loneliest warden in the
penal system." Bart, in an uncharacteristically high, feminine voice, seductively
says, "Fresh!", then takes the crowbar out of his cocktail dress and
cold-cocks the warden.
"Grift of the Magi", 19 December 1999
Bart and Milhouse are bored, so they look for interesting stuff
in Marge and Homer's closet.
Milhouse: "Wanna dress up like ladies?"
Bart: "Uhhh, wouldn't that make us kinda . . . fruity?"
Milhouse (who already has on a large wig and a bra): "Whatsa matter,
scared you might like it?"
Bart takes the (implied) challenge, and puts on a long, green dress.
Looking in the mirror, he appears to get turned on to his image,
saying, "Wow, this really hides my thighs."
The boys start jumping up and down in drag on Marge and Homer's bed,
singing "Sisters are doin' it for themselves". Soon, Homer comes
in and sees how they're dressed.
Homer: "What's going on? And I want a non-gay explanation!"
Milhouse: "Uh, we're drunk. Really drunk."
Homer: "Oh, thank God."
"Bye Bye Nerdie", 11 March 2001
Lisa and Bart are running late, and Marge is determined that
they will not miss the school bus. She brushes their teeth
both at the same time, with one brush, and so forth.
In a whirlwind, she gets them to the bottom of the stairs
almost ready, and when the dust clears (literally), Bart is
dressed in Lisa's clothes, and Lisa in Bart's.
-------------------------------------------------------------------
Sister Kate (NBC, 1989-1990)
"Hilary's Date", 29 October 1989
This is a good one, in the sense of being inventive, original. Hilary Logan
(Penina Segall) is wheelchair-bound, but her new boyfriend, Tom Schuster (Shawn
Phelan) doesn't know it. (He's only seen her sitting on the stairs, or in
a movie theatre.) Tom is invited to the costume party, so Hilary asks him
to come as Eleanor Roosevelt, so that she can be FDR and have an excuse for
the wheelchair. At one point, Hilary notes that Tom looks pretty good in
the dress and fur, "You know, kinda sexy". He bashfully seems to
agree.
-------------------------------------------------------------------
Something Special [Willy/Milly; I Was a Teenage Boy](film, 1986)
Milly Niceman (Pamela Segall) girl wonders what it would be like to be a
boy -- she wakes up one morning and finds out, as she has become Willy
Niceman; also features Malcolm (Seth Green).
-------------------------------------------------------------------
Soup and Me (TV short, 1977)
As their clothes are stolen while skinny-dipping in the river, Soup/Luther
(Christian Berrigan) and Rob (Shane Sinutko) need to wear women's clothes
to get back home.
-------------------------------------------------------------------
The Swap (TV film, 2016)
Ellie O'Brien (Payton List) and her best friend Jack Malloy (Jacob Bertrand)
get into an argument about whose life is better that gets so intense, they
actually change places. While living each other's lives, they learn about
roles and expectations, and gain empathy for one another. This is a pretty
predictable latter-day morality tale served up by Disney.
-------------------------------------------------------------------
Two and a Half Men (CBS, 2003-2015)
"I Think You Offended Don", 19 January 2009
Alan Harper (Jon Cryer) learns that his ex-wife is pregnant, after she and
he had sex during a short separation from her current husband. The child
could be his or her current husband's, but Alan obsesses on the possibility
that it is his, and that it is a girl, the daughter he's always wanted.
In a dream sequence, 14 years after the child's birth, his ex-wife comes to
the door and tells Alan that the child, who was, in fact, a girl, is his,
and has expressed the desire to live with her "real dad". Marlene
Melnick (played, of course, by Angus T. Jones [Alan's son Jake in the
series] in drag) comes to the door, scratching her butt, and asking if
Alan has anything to eat.
-------------------------------------------------------------------
Turkey Television (Nickelodeon, 1985)
[unknown episode and date]: Jason (actor unknown) wears a dress to school for
"opposite sex day".
-------------------------------------------------------------------
Two Weeks With Love (film, 1950)
Ricky Robinson (Tommy Rettig) and McCormick Robinson (Gary Gray)
dress for bed on vacation in girls' nightgowns.
-------------------------------------------------------------------
Voyagers! (NBC, 1982-1983)
"Agents of Satan", 31 October 1982
Jeffrey Jones (Meeno Peluce) dresses as an old woman to convince Salem
town elders that witch burning is wrong.
-------------------------------------------------------------------
You Can't Do That on Television (Nickelodeon, 1979-90)
many actors/actresses, many episodes
-------------------------------------------------------------------
Young Sheldon (CBS, 2017-PR)
"Killer Asteroids, Oklahoma, and a Frizzy Hair Machine", 29 March 2018
Sheldon (Iain Armitage) loses a school science fair to an entry he considers frivolous, and
decides that his school only rewards mediocrity. In a reactionary (and, it turns out, temporary)
move, he decides to give up Science and study Acting. His audition is brilliant, to say the
least, and Mr Lundy (Jason Alexander) gives him the lead in the upcoming musical: Annie.
George Sr (Lance Barber) tries to convince Sheldon that if he plays the part of a girl,
people will make fun of him. Sheldon is undeterred. He thanks his Dad for trying to protect
him, and reminds him that in Shakespeare's time, boys routinely played the part of girls.
(George mutters that if Shakespeare went to public High School, it would be a different
story.) The night of the play, Sheldon is still enthusiastically committed to the part
as he dons the costume - dress, red-curly wig and all - until he peeks through the curtain
and sees what seems to be thousands of people in his school auditorium, and his stage-fright
changes everything.
-------------------------------------------------------------------
The Zack Files (Fox, 2000-02)
"Zack Girl", 19 November 2001
This is the obligatory episode in each TV show about adolescents in which
one of the main male characters dresses as a girl. The twist here is
that Zack Greenburg (Robert Clark), who is plagued (blessed?) by paranormal
adventures in every episode, becomes a girl after he uses "Girl
Power" deodorant instead of his own. This transformation allows him
to plan to attend an all-girl sleepover ("Think of the
advantages", his friends tell him, once they realise it's really
Zack despite the long hair and girls' clothing); to find out secrets
about his own girlfriend, Sarah (Shadia Simmons); and to learn that
Gwen Killerby (Katie Boland) actually has a serious crush on Cam
Dunleavy (Jake Epstein). Of course, all the usual "hi-jinks"
are here: his male classmates, unaware that it is really Zack, find
him very attractive; he finds himself in intimate situations with
boys who think he's a girl, and has to recoil as they try to kiss him,
hold hands with him, &c.; and the oldest trick of all: he falls around
awkwardly trying to walk in women's shoes. Other clichés common
in the age of Women's Liberation include his realisation that boys
can really be jerks; and that girls are not so shallow as he once thought.
The final line of the show is a zinger. Zack's classmate Spencer Sharpe
(Michael Seater), the science nerd/paranormal investigator whose videotaped
interviews always begin and end these shows, confesses to his own camera
that there is one secret he learned which he doesn't plan to share with
anyone, ever: "The information is so unsettling, that I didn't have
the heart to tell Zack himself. [He leans into the camera to whisper.]
He was a babe!"
======================================================================== all-adult casts:
The Adventures of Priscilla, Queen of the Desert (film, 1994)
-------------------------------------------------------------------
Girls Will Be Girls (film, 2003)
Has boy actors playing some of the adult cross-dressers as children
-------------------------------------------------------------------
The Hot Chick (film, 2002)
Story of Jessica (Rob Schneider) who wakes up one morning with a, well, you know!
-------------------------------------------------------------------
The Many Loves of Dobie Gillis (CBS, 1959-1963)
"I Was a Boy Sorority Girl", 8 May 1962
[from IMDb episode summary]: To earn $20 to woo his high-class girlfriend
Samantha [Digby (Jennifer West)], Dobie [Gillis (Dwayne Hickman)] and Maynard
[G. Krebs (Bob Denver)] take a job as waiters at a sorority house party, but
when Samantha shows up as a guest, the boys become girls to avoid being detected.
[NOTE: It means they disguise themselves as girls, not "become" girls.]
-------------------------------------------------------------------
Sorority Boys (film, 2002)
-------------------------------------------------------------------
To Wong Foo, Thanks for Everything! Julie Newmar (film, 1996)
======================================================================== Books and other media:
Pretty Face No.1, Anime-style graphic novel (Shonen-Jump Manga), 2002 The blurb on the back cover of the book reads: He wanted to be her boyfriend... He'll settle for being her twin sister! When his school bus crashes, teenage karate star Rando is sent into a coma. A year later he wakes up to find that his disfigured face has been reconstructed in the image of the girl he has a crush on! Not knowing what Rando originally looked like, the mad plastic surgeon Dr. Manabe used a photo in Rando's pocket as the model for his reconstructive surgery. Abandoned by his friends and parents, the all-new Rando is mistaken for his would-be girlfriend's long-lost twin sister and adopted into her family. Can he put aside his feelings and be a good "big sister" to Rina . . . when he's still a teenage boy from the waist down?