Men in drag in the movies. What movies?
Some Like it Hot
To Wong Foo
Victor/Victoria
Mrs. Doubtfire
The Birdcage
The Crying Game
All of the Monty Python movies
What others?
Tootsie, man! How could you forget Tootsie? It’s practically a classic.
M. Butterfly
Priscilla, Queen of the Desert
The Rocky Horror Picture Show.
Elizabeth.
:smack:
The Clever Mrs. Carfax(1917), The Countess Charming(1917), Alias Mary Brown(1918), The Widow’s Might(1918), Yankee Doodle in Berlin(1919), An Adventuress(1920), The House of Mystery(1920), Old Lady 31(1920), Charley’s Aunt(1925), Madame Behave(1925), The Man on the Box(1925), The Unholy Three(1925), Money Talks(1926), Oh, What a Nurse(1926), The Romance of a Million Dollars(1926), When the Wife’s Away(1926), The First Night (1927), Oh, Baby(1927), A Sailor’s Sweetheart(1927), The Cheer Leader(1928), Charley’s Aunt(1930), The Unholy Three(1930), Maid to Order(1931), Million Dollar Baby(1934), Girls Can Play(1937), Turnabout(1940), All-American Co-Ed(1941), Charley’s Aunt(1941), Up Jumped the Devil(1941), Shut My Big Mouth(1942), Abroad with Two Yanks(1944), Goodnight, Sweetheart(1944), Boy! What a Girl!(1947), Project X(1949), Joe Palooka in Triple Cross(1951), Glen or Glenda?(1953), Varietease(1954), Teaserama (1955), Some Like It Hot(1959), Psycho(1960), Carry On Constable (1961), Watch Your Stern (1961), Bachelor Tom Peeping(1962), The House on Bare Mountain(1962), The Impersonator(1962), Surftide 77(1962), European Nights (1963), Malamondo (1964), All Men Are Apes!(1965), Beach Ball (1965), Day of the Nightmare(1965), Mondo Pazzo(1965), Paris Secret (1965), Screen Test (1965), Ski Party (1965), A Funny Thing Happened on the Way to the Forum (1966), Go, Go, Go World!(1966), Carry On Cabby(1967), Portrait of Jason (1967), The She Man (1967), Thoroughly Modern Millie (1967), Head (1968), The Name of the Game Is Kill! (1968), The Queen (1968), The Shakiest Gun in the West (1968), The Young, the Evil and the Savage (1968), Staircase (1969), Brand X (1970), Guess What We Learned in School Today?(1970), Where’s Poppa? (1970), Dressed to Kill (1980), Tootsie (1982), Ready to Wear (1994), Ed Wood (1994)
Satree Lek (Iron Ladies) is a true story about a tranvestite volleyball squad that qualified for the Olympics.
Sherlock, Jr. – Buster Keaton puts on a dress to hide from the villains. Or, rather, he leaps into one. One of the many great gags in the film.
A Woman – Short silent comedy by Charlie Chaplin in drag (though he’s playing a woman).
The Butcher Boy and Coney Island – Fatty Arbuckle; he often appeared in drag in his films. The latter is also notable because you can see Buster Keaton actually laughing.
The Unholy Three – Lon Chaney, Sr., dresses as a woman to commit crimes (two different movies)
Charlie’s Aunt – many versions, all about a student who is forced to pretend to be another student’s aunt from Brazil (where the nuts come from).
Experiment in Terror – the villain appears dressed in drag.
I Was a Male War Bride – Cary Grant dresses in drag in order to emigrate to the US (“I am an alien spouse of female military personnel en route to the United States under public law 271 of the Congress.”)
Orlando
Flawless with Robert DeNiro and Phillip Seymour Hoffman.
The Million (1914), Mrs. Black Is Back (1914), The Billionaire Lord (1915), C.O.D. (1915), Artie, the Millionaire Kid (1916), The Haunted Pajamas (1917), Some Boy! (1917), Bound in Morocco (1918), Madame Spy (1918), Around the World in Eighty Minutes with Douglas Fairbanks (1931), Clearing the Range (1931), Peach-O-Reno (1931), Sidewalks of New York (1931), Get That Girl (1932), Hypnotized (1932), Sherlock Holmes (1932), Arizona to Broadway (1933), So This Is Africa (1933), Wild Boys of the Road (1933), Circus Clown (1934), Fifteen Wives (1934), The Lucky Texan (1934), Pursuit (1935), Star of Midnight (1935), The Devil Is a Sissy (1936), Fugitive in the Sky (1936), Rose Bowl (1936), Fight for Your Lady (1937), Fit for a King (1937), Merry-Go-Round of 1938 (1937), When’s Your Birthday? (1937), Bulldog Drummond’s Revenge (1938), Peck’s Bad Boy with the Circus (1938), Up the River (1938), The Adventures of Huckleberry Finn (1939), The Amazing Mr. Williams (1939), The Ghost Comes Home (1940), Along the Rio Grande (1941), Blondie Goes Latin (1941), A Dangerous Game (1941), Double Trouble (1941), Love Crazy (1941), Sailors on Leave (1941), Arabian Nights (1942), Babes on Broadway (1942), Jail House Blues (1942), Stagecoach Buckaroo (1942), Ten Gentlemen from West Point (1942), True to the Army (1942), Two Yanks in Trinidad (1942), The Chance of a Lifetime (1943), Chatterbox (1943), Clancy Street Boys (1943), Follies Girl (1943), Gildersleeve on Broadway (1943), Jitterbugs (1943), Ali Baba and the Forty Thieves (1944), Brand of the Devil (1944), Girl Rush (1944), Lost in a Harem (1944), Riders of the Santa Fe (1944), Slightly Terrific (1944), South of Dixie (1944), The Sultan’s Daughter (1944), Sweethearts of the U.S.A. (1944), Winged Victory (1944), Here Come the Co-Eds (1945), I’ll Remember April (1945), Radio Stars on Parade (1945), Springtime in Texas (1945), Trouble Chasers (1945), Dangerous Money (1946), Girl on the Spot (1946), Gunman’s Code (1946), Border Feud (1947), The Wistful Widow of Wagon Gap (1947), Jiggs and Maggie in Court (1948), Mexican Hayride (1948), Abbott and Costello Meet the Killer: Boris Karloff (1949), The Adventures of Ichabod and Mr. Toad (1949), I Was a Male War Bride (1949), On the Town (1949), Belle of Old Mexico (1950), The West Point Story (1950), As You Were! (1951), At War with the Army (1951), The Lemon Drop Kid (1951), No Questions Asked (1951), Paris After Midnight (1951), Buffalo Bill in Tomahawk Territory (1952), The Crimson Pirate (1952), Geisha Girl (1952), Gobs and Gals (1952), Hold That Line (1952), Lady in the Iron Mask (1952), Meet Me at the Fair (1952), A Virgin in Hollywood (1952), Where’s Charley? (1952), Willie and Joe Back at the Front (1952), Calamity Jane (1953), The Man Behind the Gun (1953), Private Eyes (1953), Scared Stiff (1953), Stalag 17 (1953), Titanic (1953), Casanova’s Big Night (1954), Francis Joins the WACS (1954), Money from Home (1954), White Christmas (1954), Everything but the Truth (1956), The Killer Is Loose (1956), Looking for Danger (1957), The Matchmaker (1958), The Adventures of Huckleberry Finn (1960), High Time (1960), The Savage Eye (1960), Under Ten Flags (1960), Young Jesse James (1960)
I just came in to scream “Flawless!” (Glares at myskepticsight) 
What a great movie. Phillip Seymour Hoffman is the best dramatic actor ever.
Rat Race has a male Lucille Ball impersonator
Miss Congeniality 2 has numerous males impersonating female celebrities
I just wanted to say that I hated hated hated that movie. I don’t know why. Maybe it was something I ate.
Back to the Future II
Shakespeare in Love
Edward D Wood’s opus:
Glen or Glenda?
Starring Bela Lugosi.
The Rose
Vegas In Space.
Tango and Cash