Madonna (and Depeche Mode) are two artists who i feel have 'been with me' every step of my adult life. I went to school in San Francisco from Los Angeles starting in 1982 and I so remember sitting on some bus bench in Redondo Beach CA , about 1983 or so, visiting my father and listening to Borderline on my Aiwa cassette/radio thingy on the radio. I think that was her first big hit. Interesting trivia on Borderline, there are two versions, one has a string of violins playing here and there and one does not have it. I prefer the former to be honest as I love the strings in that. Both were equally played, have no idea why they were different though.
But Madonna really has been a part of every part of my life, every place I've lived (even France in 1985/86 when I saw "Recherche Susan, Desesperement" at some theatre in Aix en Provence and when True Blue was out in America but not in Europe yet).
I would guess many of us old time fans can remember many of her singles and where we were living, or what we were going through in our lives at the time. I certainly do.
I've not followed her too much in the past few years however.. I think Celebration was the last 'hit' I remember. 30 years is a top milestone for any artist to strive for. She definitely is not all smoke and mirrors.