I am not the biggest fan of Madonna's work. However, there are some tracks for which I have a great deal of love &/or respect.
For me, mainly due to memories from when I turned twenty, my first song has her playing a born-again virgin, "Like A Virgin" (1984). The video really takes me back to the hairstyles and fashions of the mid-1980s. Another reason for liking this song is that back in the late 1990s, it was one of my two staple karaoke tracks, which I sang in an acceptable (and oddly appreciated!) baritone:
My all-time favourite Madonna song with video is "Frozen" (1998):
I find the video intellectually, emotionally and spiritually stimulating: intellectually because my degree in Theology & Religious Studies comes to bear; emotionally as I recall an ex-lover who just would not let me in; spiritually in the numinous moments I experience whilst listening.
It is interesting that the Wikipedia article, which is really far better than I at discussing the track, in so doing fails to make any mention nor reference to the mythological Djinn let alone witches. Nor in their article on Djinn is there a cross-reference in the popular cultural references section.
There are a couple of paintings that I personally see as perhaps having a pictorial &/or symbolic connection with the video; thus adding a further emotional connection for myself.
The first is Malcolm T. Liepke's portrait of a shapeless woman swathed in all-encompassing black robes with flowing black hair.
The second is a painting by Giovanni Sagantini entitled "Le cattive madri" translated as "The bad/evil Mothers" (1894, purchased by the Austrian state in 1902) which usually hangs in Vienna's Belvedere Museum.
Above all, she is an erotic-orgiastic woman in whom Segantini conjoins the biological conflict between motherhood/sexuality, freedom/captivity.
These are themes upon which Madonna's œuvre has frequently touched.
Perhaps interestingly and co-incidently, Madonna begins the next video also attired in black with wind-blown, long black hair. I love the way the song commences as a plaintive cry of desperation and ultimately explodes in a gospel-choir hope-filled crescendo. It makes me horripilate every time!
Herewith, "Like A Prayer" (1989):
My next two favourites are related to films (movies). The first is from a film panned by critics, but which I oddly adored (despite being far from a fan of Warren Beatty). Madonna, as far as I am concerned, entertained best on celluloid in "Dick Tracy". Here you go with a bit of spanky (perhaps receiving six of the best*!) in "Hanky Panky" (1990):
And the other film-track is from a film in which, apart from singing the eponymous title song, she also played the rôle of a sword-wielding dominatrix named Verity. (Her second-best acting part to my mind.) Of course, it is the James Bond film "Die Another Day" (2002). It was refreshing to see the credits of a 007 picture used to further the tale rather than just being an excuse to showcase semi-clad &/or nude females.
Finally, a track I love to listen to due to the sample from "Gimme, Gimme, Gimme (A Man After Midnight)" by ABBA and due to it bringing to mind my best friend & ex-partner. This is a fantastic fusion of ABBA & Madonna which produced a revivifying dance anthem mixed with a nostalgic tang. Alas, Madge's choice of attire, makes the accompanying video hard to view without squirming! But perhaps that is just my hang-up? Herewith, "Hung Up" (2005):
Hope you like my selections. Do you agree with my top Madonna choices? If not, which tracks would make your list and why? To assist here is a link to her full singles discography.
* = "six of the best Brit., chiefly historical or humorous a caning as a punishment, traditionally with six strokes of the cane." (sic)