Ducking in to share my limited Judy Garland knowledge.
She was a daddy's girl, her dad died in her prepubescent years and he was not straight. They left MN for CA after he was caught with a young man. After his death she had both dad issues and gay man issues. A couple of her husbands were not straight, actually. Most of her friends were not either. In the 60's she was asked about her gay following and she said something along the lines of "I don't care, I sing to people."
There was also a famous instance in the pre civil rights years where she danced with Sugar Ray Robinson that got people's attention. 1950 or so?
Also, plenty of rumors that she'd take affection where ever she could find it, cough Kay Thompson cough.
So, being nice to gay dudes, not treating black people like crap and not being averse to a little free love apparently equaled gay icon back in the day.
P.S. SRD, please don't make me regret my love for Jesse James Meets Frankenstein's Daughter by comparing Dorothy to those Twilight shits. Dorothy was invented in 1900 and this representation was 1939. She was cornbelt naive. She's overwhelmed. Gobsmacked. Bumfuzzled. You'd gawk too if you magically went from sepia, dusty cornfields to, uh, vivid, technicolor cornfields! Also, murders! She didn't stammer and blink, she stammered and killed.