This is the answer to an entirely different question, but I feel it answers the OP rather nicely.
From Yahoo | Mail, Weather, Search, Politics, News, Finance, Sports & Videos
"Dear Yahoo!:
Why is Judy Garland such a popular gay icon?
Auntie Em
Encino, California
Dear Em:
Somewhere over the rainbow, past searches on “Judy Garland gay icon” and related terms, we discovered a number of complicated reasons why this singer and movie star is so beloved by the gay community.
The gay and lesbian magazine The Advocate calls Judy Garland “an Elvis for homosexuals.” In more closeted times, gays used the term “friend of Dorothy” to refer to themselves in mixed company, in homage to Garland’s role as Dorothy in The Wizard of Oz. Today, Garland isn’t as well known among the younger gay generation, but she still holds a special place in the hearts of many.
Judy Garland was hugely popular among gays during her lifetime. Her concerts were major gay meeting places, and in her later years, she made money singing at gay piano bars. Garland’s father was gay, as were her studio-executive mentor and two of her five husbands. She had many gay friends and went to parties where she joked that she was the only woman present. But her appeal was based on more than her own acceptance of gays.
Both onscreen and off, Garland projected a unique combination of vulnerability and strength. She sang of intense loneliness, followed by songs describing delirious love. She had legendary stage fright but declared her greatest happiness came from performing. These conflicts mirrored the lives of oppressed, closeted gay men in the 1950s and 1960s. They identified with the paradox and duplicity in Garland’s life. Severe laws and prejudice against homosexuality forced gays to lead double lives and hide their true selves.
As Dorothy, Judy Garland portrayed a misunderstood kid from a small town who has an amazing adventure in a Technicolor world. The central message of The Wizard of Oz is that you will find what you’re looking for inside yourself. That message resonated with gays of the era who yearned to come out into a colorful world and live what was inside of them.
While prejudice against gays is still common, the public is generally more tolerant these days. Homosexuals aren’t as strictly closeted as in Garland’s day, and her image doesn’t strike such a deep chord. But her plucky strength and sweetness continue to win admirers among people of all orientations. "