First cross-dressing movie? (Eve?)

There’s a new movie coming soon about an NBA star who dresses as a woman in order to play for the WNBA. It’s gonna suck, of course, but waddya gonna do? What was the first movie in which a male character has to/chooses to dress like a woman for whatever reason? I checked the IMDB and found that Glen or Glenda came out (so to speak) before Some Like It Hot. Is there an earlier example? Eve?

Well, there’s a scene in The Crimson Pirate (1952) in which Burt et. al. dress up as “local girls” to fool the British Governer… but it’s probably not the oldest scene of it’s kind.

In fact, i’d assume the first cross-dressing movie was the first time anyone pointed a camera at a production of The Merchant of Venice.

The earliest I can think of is Charlie Chaplin in The Woman (1915) and Lon Chaney in The Unholy Three (1925)

Harold Lloyd in Spit-ball Sadie (1915) and Chaplin again in The Masquerader (1914)

A Florida Enchantment (1914) features a woman charachter who dresses up to impersonate a man.

Everyone else—movie buffs and cross-dressers alike—has already answered for me. Cheers!

Thanks for the info. I’m surprised it goes back that far!

From IMDB, a list of things pre-dating 1960 that have some element of cross-dressing or transvestisism. I make no claim the list is accurate or complete, just that these are movies which listed “cross-dressing,” “tranvestisism,” or “drag” in their keywords.

The second on the list is female to male, but it may be the earliest where cross-dressing had a sexual/romantic purpose. Apparently the lead takes some pill that causes her to take after women; she then dresses like a man to have a chance with them.

The Leading Lady, 1911
A Florida Enchantment, 1914 (female to male)
A Woman, 1915
The Butcher Boy, 1917
Doing His Bit, 1917
Yankee Doodle in Berlin, 1919
Charley’s Aunt, 1930
The Man from Monterey, 1933
Släkten är värst, 1936 (Sweden)
Sylvia Scarlett, 1936
La Grande Illusion, 1937 (France)
Charlie’s Big Hearted Aunt, 1940
Charley’s Aunt, 1941
Blåjackor, 1945 (Sweden)
Lilla helgonet, 1944 (Sweden)
Fram för lilla Märta, 1945 (Sweden)
Lilla Märta kommer tillbaka, 1948 (Sweden)
Glen or Glenda, 1953
Casey Bats Again, 1954
Charleys Tante, 1955 (West Germany)
Glade skomakaren, Den, 1955 (Swede)
Weiching jiande, 1955 (Hong Kong)
Pablo y Carolina, 1957 (Mexico) (female to male)
Dragstrip Riot, 1958
Some Like it Hot, 1959
Voulez-vous danser avec moi?, 1959 (France)

According to the IMDB, the first film version of As You LIke It was released in 1908. The first film version of The Merchant of Venice was the same year, and then there was Twelfth Night in 1910.