Sylvia Scarlett (1935): Somehow this movie dodged my radar for twenty-five years. Katherine Hepburn (who I love) dresses up as a fellah to avoid the coppers. She's doesn't really look like a boy but seems to trick everyone with her deep voice and pants. She and her fugitive father meet up with Cary Grant (donning a terrible cockney accent) and a British maid and naturally, they start a traveling comedy show. It's a weird movie but along with Adam's Rib, Born Yesterday, My Fair Lady, and The Philadelphia Story, has convinced me to see everything George Cukor ever directed.
Just One of the Guys (1985): I was having trouble deciding which cross-dressing movie to choose. I narrowed it down between Glen or Glenda, Tootsie, and In Like Flint. Then I showed Whitney the trailer for Just One of the Guys and she begged me to choose it. She's chosen some of my recommendations for previous marathons (you can thank me for The Initiation) so I returned the favor. This is one of your typical "girl dresses up like a boy for equality" movies. It's like Yentl with more nudity. "We Love the 80s" loves this movie. That meant that I knew the ending before we even put the DVD in. But it was great, 80s teen-com. Really underrated.
I Was a Male War Bride (1949): Two Cary Grant movies in one night! We're classy. In this one, Cary Grant plays a French military man (donning absolutely no accent at all) who falls in love with Ann Sheridan, an American military gal who gets on his last nerve. When they decide to get married, they have to go through U.S. Military-grade red tape and Grant is forced to stay awake for about three days straight. Honestly, hoping Grant finds a bed to sleep in becomes a bigger subplot than their trip around the world. If you're only watching this for the cross-dressing, be prepared to wait about an hour and half to see it.
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