Here’s the Wikipedia entry on Oz:
http://en.wikipedia.org/wiki/Portal:Oz
There’s a list of all the Oz books, each of which links to an article which gives the plot of the book. Go through the plots of the first fourteen books (those that Baum wrote). Tell me just how many events in those books, even in a strained Freudian interpretation, can be taken as having some homosexual connotation (or even a transsexual connotation). Lots of odd events happen in the books, but I don’t see how they could be taken as generally implying anything about Baum’s sexual orientation, even if you insist on this Freudian business of taking things said about a character as applying to the author.
As far as I can tell, there was no connection made between male homosexuals and the 1939 movie (and Judy Garland) until the early 1950’s, and this connection began to be considered an older, fading image of male homosexuals by the late 1960’s. It’s likely that Garland first became a gay icon in the early 1950’s when she made her first return to fame after fading in popularity in the 1940’s. She certainly wasn’t thought of as a gay icon in 1939. She was the all-American girl back then who everyone thought would become a great actress and singer as an adult. By the early 1950’s, it was clear that she would have a turbulent life and career. She was already thought of as a tragic figure. This sort of tragic, drama-queen singing diva was exactly the sort of figure that became gay icons back then.
It was probably around that time that gay men began looking at the 1939 movie The Wizard of Oz, which after a period of neglect had begun to be shown every year on TV, and started seeing things in it which fit into their gay-icon worldview. They saw it as being about only being able to find happiness in a dream world. When they connected this with the tragic image of Garland, they decided that this all fit together and made the movie and Garland gay icons.
The interesting thing is that this is at wide variance with the books (and even with the movie). In the books, Oz is not a dream world. It’s a real world which is repeatedly visited in the Oz series. Dorothy Gale in the books is not a tragic figure. The filmmakers changed this to make Oz merely part of Dorothy’s dreams. I’m not sure why. Maybe they thought that straight fantasy wouldn’t be popular. They movie is much more sentimental than the books. In the books, Dorothy is not a poor lost girl who only thinks of home but an adventurer. Maybe it was just that movies with tragic women who long for home and can’t find happiness were popular that year. After all, Gone with the Wind also came out that year.
(Incidentally, the song “Somewhere over the Rainbow” encapsulates the search for happiness in some unattainable world. I think it’s a great song, but I also don’t think that Judy Garland did that great a version of it in the movie. The version by Israel Kamakawiwo’ole is distinctly better. The version by Eva Cassidy is better yet.)
Interestingly then, by the time that Judy Garland died in 1969, the whole business of gay men making tragic-diva figures into gay icons had faded. By the late 1970’s, it was clear that tragedy was out and gay men were into a hyper-masculinity thing. It appears to me that this was already true in 1969. In the movie Midnight Cowboy (that year’s Oscar winner), a young man from Texas goes to New York thinking he can hustle rich women with his cowboy stud image. People there tell him that rich woman don’t like that anymore, but if he wants to hustle gay men that they are into that sort of thing.