I'm old enough to remember early Madonna, 1980s Madonna, the Madonna of 'Holiday', the Madonna of 'Desperately Seeking Susan'. She was fresh, with her own distinct style of dressing, catchy tunes and great performances. It was the early days of music videos too, and hers were brilliant.
It started to go a bit tits-up in the 90s with her dreadful coffee-table book called 'Sex' and the 'Erotica' album. She was busy chasing being taken seriously as an actress too, I do sometimes wonder if she found she'd painted herself into a corner, image-wise, with the soft porn look she was playing with at the time.
Like many big female singers, she always had a following of gay men - disco was heavily influenced by that scene back then, so it's no surprise that she'd have Pride. Unfortunately, her pampered lifestyle of the past few decades will have given her the ivory-tower viewpoint, where she cannot see the difference between LGB and T.
Happy to see her drape herself in the rainbow. Just wish she knew what she was endorsing if she chooses the execrable Progress (how deceiving a name is that) flag of the trans flag. I doubt she does.