Who was that lady I saw you with?

...that was no lady. What film most effectively makes use of cross dressing?

Poll suggested by horn-5.

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1.
Dressed to Kill (1980)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
A mysterious blonde woman kills one of a psychiatrist's patients, and then goes after the high-class call girl who witnessed the murder. (105 mins.)
Director: Brian De Palma
 
2.
Some Like It Hot (1959)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
When two male musicians witness a mob hit, they flee the state in an all-female band disguised as women, but further complications set in. (121 mins.)
Director: Billy Wilder
 
3.
Staircase (1969)
    1 2 3 4 5 6 7 8 9 10 5.3/10 X  
Charles Dyer and Harry Leeds are a couple that have been living together for nearly 20 years. Both earn... (96 mins.)
Director: Stanley Donen
 
4.
What's Opera, Doc? (1957 Short Film)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
Elmer Fudd is again hunting rabbits - only this time it's an opera. Wagner's Siegfried with Elmer as the titular hero and Bugs as Brunnhilde. They sing, they dance, they eat the scenery. (7 mins.)
Director: Chuck Jones
 
5.
The Mouse That Roared (1959)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
An impoverished backward nation declares a war on the United States of America, hoping to lose, but things don't go according to plan. (83 mins.)
Director: Jack Arnold
 
6.
Tootsie (1982)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Michael Dorsey, an unsuccessful actor, disguises himself as a woman in order to get a role on a trashy hospital soap. (116 mins.)
Director: Sydney Pollack
 
7.
Rebecca's Daughters (1992)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
The film is set in Wales and concerns itself with the aristocracy who are taxing to common people to ruin... (96 mins.)
Director: Karl Francis
 
8.
The Birdcage (1996)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
A gay cabaret owner and his drag queen companion agree to put up a false straight front so that their son can introduce them to his fiancée's right-wing moralistic parents. (117 mins.)
Director: Mike Nichols
 
9.
Psycho (1960)
    1 2 3 4 5 6 7 8 9 10 8.5/10 X  
A Phoenix secretary embezzles $40,000 from her employer's client, goes on the run, and checks into a remote motel run by a young man under the domination of his mother. (109 mins.)
 
10.
Morocco (1930)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A cabaret singer and a Legionnaire fall in love, but their relationship is complicated by the results of his womanizing and due to the appearance of a rich man who wants her for himself. (92 mins.)
 
11.
Monty Python's Flying Circus (1969 TV Series)
    1 2 3 4 5 6 7 8 9 10 8.9/10 X  
The original surreal sketch comedy showcase for the Monty Python troupe. (30 mins.)
 
12.
Sullivan's Travels (1941)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
A director of escapist films goes on the road as a hobo to learn about life, which gives him a rude awakening. (90 mins.)
Director: Preston Sturges
 
13.
I Was a Male War Bride (1949)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
Henri Rochard is a French captain assigned to work with Lt. Catherine Gates. Through a wacky series of misadventures... (105 mins.)
Director: Howard Hawks
 
14.
Victor Victoria (1982)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A struggling female soprano finds work playing a male female impersonator, but it complicates her personal life. (132 mins.)
Director: Blake Edwards
 
15.
Yentl (1983)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
A Jewish girl disguises herself as a boy to enter religious training. (133 mins.)
 
16.
The Rocky Horror Picture Show (1975)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
A newly engaged couple have a breakdown in an isolated area and must pay a call to the bizarre residence of Dr. Frank-N-Furter. (100 mins.)
Director: Jim Sharman
 
17.
To Wong Foo Thanks for Everything, Julie Newmar (1995)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
Three drag queens travel cross-country until their car breaks down, leaving them stranded in a small town. (109 mins.)
Director: Beeban Kidron
 
18.
Mrs. Doubtfire (1993)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
After a bitter divorce, an actor disguises himself as a female housekeeper to spend time with his children held in custody by his former wife. (125 mins.)
Director: Chris Columbus
 
19.
Gypsy (1962)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Based on the Broadway hit about the life and times of burlesque dancer Gypsy Rose Lee and her aggressive stage mother, Mama Rose. (143 mins.)
Director: Mervyn LeRoy
 
20.
Queen Christina (1933)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Queen Christina of Sweden is a popular monarch who is loyal to her country. However, when she falls in love with a Spanish envoy, she must choose between the throne and the man she loves. (99 mins.)
 
21.
Paris Is Burning (1990 Documentary)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
A chronicle of New York's drag scene in the 1980s, focusing on balls, voguing and the ambitions and dreams of those who gave the era its warmth and vitality. (71 mins.)
 
22.
Bosom Buddies (1980 TV Series)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
Two young single ad men must disguise themselves as women to live in the one apartment they can afford. (30 mins.)
 
23.
Tokyo Godfathers (2003)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
On Christmas Eve, three homeless people living on the streets of Tokyo find a newborn baby among the trash and set out to find its parents. (93 mins.)
 
24.
Charley's Aunt (1941)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
In 1890, two students at Oxford force their rascally friend and fellow student to pose as an aunt from Brazil--where the nuts come from. (80 mins.)
Director: Archie Mayo
 
25.
Little Big Man (1970)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Jack Crabb, looking back from extreme old age, tells of his life being raised by Native Americans and fighting with General Custer. (139 mins.)
Director: Arthur Penn
 
26.
Boys Don't Cry (1999)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Female-born Teena Brandon adopts his male identity of Brandon Teena and attempts to find himself and love in Nebraska. (118 mins.)
Director: Kimberly Peirce
 
27.
The Adventures of Priscilla, Queen of the Desert (1994)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
Two drag performers and a transgender woman travel across the desert to perform their unique style of cabaret. (104 mins.)
Director: Stephan Elliott
 
28.
Mulan (1998)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
To save her father from death in the army, a young maiden secretly goes in his place and becomes one of China's greatest heroines in the process. (88 mins.)
 
29.
Shakespeare in Love (1998)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A young Shakespeare, out of ideas and short of cash, meets his ideal woman and is inspired to write one of his most famous plays. (123 mins.)
Director: John Madden
 
30.
Stage Beauty (2004)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A female theatre dresser creates a stir and sparks a revolution in seventeenth century London theatre by playing Desdemona in Othello. But what will become of the male actor she once worked for and eventually replaced? (106 mins.)
Director: Richard Eyre
 
31.
The Big Bad Wolf (1934 Short Film)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
The two foolish little pigs escort Red Riding Hood on a short cut through the woods, against the advice of their bricklayer brother... (9 mins.)
 
32.
Monty Python and the Holy Grail (1975)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
King Arthur and his knights embark on a low-budget search for the Grail, encountering many, very silly obstacles. (91 mins.)
 
33.
Lost in a Harem (1944)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Two bumbling magicians help a Middle Eastern prince regain his rightful throne from his despotic uncle. (89 mins.)
Director: Charles Riesner
 
34.
Robin Hood: Men in Tights (1993)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A spoof of Robin Hood in general and Robin Hood: Prince of Thieves in particular. (104 mins.)
Director: Mel Brooks
 
35.
The Wife of Monte Cristo (1946)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
Edmund Dantes (Martin Kosleck), The Count of Monte Cristo, rides again in 1832, this time accompanied by (or stood in for) his countess wife... (83 mins.)
Director: Edgar G. Ulmer