Murder! (1930), Marilyn (2018), Venus Boyz (2002), Monty Python Live at the Hollywood Bowl (1982), Victor Victoria (1982), Tootsie (1982), Breakfast on Pluto (2005), Twelfth Night (1996) ... Let's take a look at the ranked list of the best Cross-dressing movies.
Storyline: Based on a true story, this is the tale of Josephine Monaghan, a young woman of the mid nineteenth century who is thrown out of her parents' home after being seduced by the family's portrait photographer and giving birth to his child. Josephine quickly learns that young, female, pretty, and alone are a bad combination for life in the wild west. In her desperation to survive, Josephine disguises herself as "Jo", a young man, and struggles to make a life for herself in a dingy frontier mining town. Can "Little Jo" live and love without revealing his secret?—Martin Lewison <lewison@pitt.edu>
Plot Keywords: young woman, stableman, shepherd, wife, laborer, businessman, powerful ...
Movie Details Click Here!Storyline: In 19th century Dublin, Albert Nobbs, an eccentric man in the latter part of middle age, works as a waiter in Morrison's Hotel run by the stingy and controlling Marge Baker. Albert is hard working and saves his money so that one day he will be able to eke out a better life for himself by owning his own business rather than work at the hotel. Beyond his work colleagues, he is all alone in the world. One day, a man named Hubert Page is hired by Mrs. Baker to paint one of the rooms in the hotel. She forces Hubert to share Albert's bed for the one night he is required to stay to complete the work, much to Albert's horror. Hubert discovers the reason Albert did not want to share a room with him. But rather than the issue being a problem, Hubert shows Albert that he can follow a slightly different life path than the one he envisioned for himself - one closer to the life that Hubert leads with his wife Cathleen - which includes getting married and having a wife to support him emotionally. ...
Plot Keywords: butler, transvestite, painter, maid, partner, love interest, emotional ...
Movie Details Click Here!Storyline: Terry Griffith has got it all -- looks, popularity, the perfect college boyfriend, and an article that's a shoo-in to win her a summer internship at the local newspaper... or so she thinks. When Terry's journalism teacher passes her article up in favor of a couple of pieces written by boys, Terry is convinced that sexism is to blame. Determined to win the internship at any cost, Terry goes undercover at a rival high school to resubmit her article... as a boy. But Terry gets more than she bargained for when she finds herself fending off a bully and the advances of an oversexed female admirer, and falling for her new pal Rick.
Plot Keywords: high-school student, college student, reporter, brother, girl, love interest, amusing ...
Movie Details Click Here!Storyline: Eastern Europe, 1904. A Jewish woman, Yentl, has a thirst for knowledge but is prohibited from learning due to the restrictions of her religion. When her father dies, she sets off to increase her knowledge, posing as a man in order to gain admission to a Jewish religious school.
Plot Keywords: young girl, father, teacher, love interest, roommate, passionate, heartwarming ...
Movie Details Click Here!Storyline: A 14 year-old-boy, struggling with gender identity and religion, begins to use fantasy to escape his life in the inner city and find his passion in the process.
Plot Keywords: teen boy, mother, brother, aunt, drag queen, transgender woman, emotional ...
Movie Details Click Here!Storyline: Humble Maria (Claire Danes), who outfits top London theater star Ned Kynaston (Billy Crudup), takes none of the credit for the male actor's success at playing women. And because this is the 17th century, Maria, like other females, is prohibited from pursuing her dream of acting. But when powerful people support her, King Charles II (Rupert Everett) lifts the ban on female stage performers. And just as Maria aided Ned, she needs his help to learn her new profession.
Plot Keywords: actor, actress, king, girlfriend, nobleman, spirited, uplifting ...
Movie Details Click Here!Storyline: After accidentally witnessing a mafia hit in the Windy City, gal pals Connie and Carla skip town for L.A., where they go way undercover as singers working the city's dinner theater circuit ... as drag queens. Now, it's not enough that they become big hits on the scene; things get extra-weird when Connie meets Jeff -- a guy she'd like to be a woman with.—Anonymous
Plot Keywords: friend, singer, club owner, drag queen, love interest, witness, amusing ...
Movie Details Click Here!Storyline: Boston Blackie and his pal, The Runt, are ready to board a train for Florida when Blackie gets a telegram from his friend Arthur Manleder asking Blackie to go to Manleder's New York apartment, get $60,000 from a wall safe and fly to Hollywood. Blackie has just removed the money when Police Inspector Farraday and his assistant, Sergeant Matthews arrive and accuse him of robbery. They let him escape so they can follow as they think he knows something about the stolen Monterey Diamond. Blackie arrives in Hollywood and learns that Manleder has fallen for Gloria Lane, in cahoots with a gang of crooks, and had been holding the missing diamond in trust for the owner. Gloria had asked Arthur to let her wear the diamond and it was stolen. Two gangsters had appeared at the apartment and offered to recover the diamond for $60,000, which had prompted the telegram to Blackie. The two crooks also steal the money from The Runt. Blackie's plan to catch the crooks and recover the money and the diamond goes awry when another crook, Slick Barton, steals both from his two crook pals. Farraday and Matthews now arrive and accuse Blackie of both thefts.—Les Adams <longhorn1939@suddenlink.net>
Plot Keywords: ex-convict, police detective, sidekick, millionaire, jewel thief, nemesis, lighthearted ...
Movie Details Click Here!Storyline: Bruno is the story of a unique young boy genius, Bruno (Alex D. Linz), whose expression of his own individuality leads his family and community along an emotional journey. By the time he reaches his final destination, Bruno's story becomes a fable of the importance of each person's uniqueness and originality.—Anonymous
Plot Keywords: student, mother superior, police officer, mother, classmate, offbeat, amusing ...
Movie Details Click Here!Storyline: Junior high in a time of rotary phones. Cougars have been spotted in the area. Logan is 13, the odd kid, with an active imagination and few friends. His young, single mother seems stressed. Latency is giving way to puberty, and Logan, who keeps a tube of lipstick in his dresser, may be gay or, more mysterious, transgender. He stares at himself in the mirror. He becomes friends with Rodeo, older and more mature, good-looking, with girlfriends. They take walks. Logan calls Rodeo and pretends to be a girl. Will he disclose himself to Rodeo? The kids at school talk. The school wants to promote kindness and tolerance. There are stories of child suicide. How do we find our way?—<jhailey@hotmail.com>
Plot Keywords: teen boy, mother, classmate, therapist, brooding, engaging, house ...
Movie Details Click Here!Storyline: Michael King is a seedy writer of sleazy pulp genre novels under a half-dozen sensational pseudonyms whose ambition is to dictate ten thousand words per minute to stenographers a la Earle Stanley Gardner. He's recruited by the agent of Preston Gilbert, a quirky ex-Hollywood star currently living reclusively in exile in Malta, to help him write his biography. Despite being pursued by an enigmatic hitman, Gilbert has a large entourage of eccentrics and remains an inveterate practical joker. After Gilbert is eventually murdered by an apparent Priest, King tries to stay alive while interacting with a variety of idiosyncratic characters including an ersatz Princess, a henpecked clairvoyant, and a cross-dressing hitman.—G. Taverney (duke1029@aol.com)
Plot Keywords: author, actor, princess, clairvoyant, priest, hit man, amusing ...
Movie Details Click Here!Storyline: Louis, a young teacher enamored of the age of F. Scott Fitzgerald, loses his job when he's caught trying on a bra he finds in a campus office. He decides to go to New York City to find himself and to be a writer. He answers an ad for a housemate placed by the eccentric and opinionated Henry Harrison; an odd-couple relationship starts. Louis gets a job selling advertising for a green magazine and fancies Mary, a co-worker. He meets Henry's neighbor, the hirsute Gershon, and Henry offers Paul schooling in the gentleman's world of being an "extra man" - a hired companion, a gigolo - for older women. Can Louis sort out these varied worlds as well as his own expectations?—<jhailey@hotmail.com>
Plot Keywords: extra, professor, escort, amusing, new york city, literature, cross-dressing ...
Movie Details Click Here!Storyline: Set in New Zealand in the summer of 1975, 50 Ways of Saying Fabulous is the story of 12 year-old Billy, who is about to discover that growing up is a lot more confusing than he could have ever imagined. He is a farmer's only son who is out of step with the other boys at his school. He feels they only want to fight and play rugby and while he tries to be the same, he feels he was never cut out to be a farmer or a rugby player. Instead, he prefers to dream about an imaginary life in outer space. In this world, a turnip paddock becomes a lunar landscape and a cow's tail a head of beautiful blonde hair which transforms him into "Lana" the heroine of his favorite TV show. With the arrival of Roy, the class freak, and Jamie the sexy young farm laborer Billy's world is changed forever. As he learns about his sexuality, everything he knows is called into question, including his lifelong loyalty to his best friend, tomboy Louise, whose world is changing alongside his. Set in New Zealand's Central Otago landscape.—Rachael Fleury
Plot Keywords: young boy, outcast, neighbor, farmhand, cousin, tomboy, endearing ...
Movie Details Click Here!Storyline: After being falsely accused of stealing the budget for their annual cocktail cruise, three very different fraternity brothers are kicked out of their dorm. In order to clear their name and to secure their future careers, the three dress up in drag and pledge the sorority next door where they learn a few valuable - and hilarious - lessons about themselves and the female species.
Plot Keywords: frat boy, chauvinist, friend, sorority sister, nerd, sexy woman, amusing ...
Movie Details Click Here!Storyline: On a college ski weekend, Todd and Craig pretend to be Jane and Nora, a pair of English girls. Their reasons? To meet girls, and to learn to ski. Along the way, Lesley Gore shows up on the bus to sing "Sunshine, Lollipops, and Rainbows", and James Brown and the Famous Flames appear at the lodge to sing "I Feel Good".—GlennR
Plot Keywords: college student, impostor, young woman, cross-dresser, love interest, skier, campy ...
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