Pre-1969 content (or as i like to think of it in cinema history terms, pre-Funeral Parade of Roses) ranging from genderbending that rises above the typical crossdressing capers of the time, to representations of formal, codified transness, and real-life trans people (names given in notes).
Not on Letterboxd:
London and Denmark travel films by Christine Jorgensen, 1951-53. (More info: conservancy.umn.edu/bitstream/handle/11299/101833/1/Franklin_umn_0130E_11767.pdf cinema.usc.edu/spectator/37.2/2_Horak.pdf)
(https://soeg.kb.dk/discovery/fulldisplay?docid=alma99122069881405763&context=L&vid=45KBDK_KGL:KGL&lang=en) copyrighted until 2035
various Christine Jorgensen newsreels 1953-54 (https://www.digitaltransgenderarchive.net/catalog?f%5Bcollection_name_ssim%5D%5B%5D=Christine+Jorgensen+Collection&f%5Bgenre_ssim%5D%5B%5D=Motion+Pictures)
It's a Camp! — Barry Pollock (1969)
ROBERTA WINS HILL CLIMB (1957) (https://www.britishpathe.com/asset/186527/)
SOUTH AFRICA: WOMAN WHO HAD SEX CHANGE IS NOW HAPPILY MARRIED; INTERVIEW WITH MR AND MRS ASHLEY (1965) (https://www.britishpathe.com/asset/214037/)
AUSTRIA: FORMER AUSTRIAN WOMAN CHAMPION SKIER BEGINS TRAINING FOR MEN'S SKI EVENTS - AFTER SEX CHANGE. (1968) (https://www.britishpathe.com/asset/201580/)