I'm not a fan though I admit to liking a couple of her old songs. What I admire is her guts and even more her open mind...
This pretty much sums what where I am with Madonna artistically. She had a nice run of catchy songs in the late 80's - early 90's:
- Like a Prayer
- This Used to Be My Playground
- Papa Don't Preach
- La Isla Bonita
- Express Yourself
- Cherish
- Oh Father
However, I don't think Madonna ever "courted" the gay audience - she didn't have to because they found her first (like Bette Midler, ten years before).
But for me, the Madonna - Gay alliance was cemented in 1985 when
Penthouse magazine published nude photographs that she had done years earlier when she needed the money. This had all the makings of the classic pop career killing scandal. But unlike anyone before her (that I can remember), Madonna didn't back down or show any kind of embarrassment or remorse. She owned it, and essentially shrugged "So what?". And her career chugged on as if nothing had happened. As a matter of fact, there is a reference to it in one of her movies:
Madonna: What if at a key moment in the game my, my uniform bursts open and, uh, oops!, my bosoms come flying out? That, that might draw a crowd, right?
Rosie O'Donnell: You think there are men in this country who ain't seen your bosoms?
- from the movie "A League of Their Own"
I think for a lot of gay men that illustrated the situation they found themselves in: If they come out (or are discovered) then they are ridiculed, embarrassed, or somehow marginalized. Madonna illustrated another way - hold your head up high and own who you are and fuck 'em if they can't deal with it.
Madonna drew many gay fans, and as others have mentioned, it was the way she acknowledged and even flaunted her gay status (again, like Bette before her), that made her different.