Madonna's Fashion Evolution: 50 Iconic Looks
Madonna's Fashion Evolution: 50 Iconic Looks

3. 'Frozen'

1998

The video for this Hot 100 No. 2 ballad conveys the song's bleak heartbreak perfectly with a gimlet-eyed Madonna shrouded in black on an ominously barren field, waving her hennaed hands as she falls backwards, turning into a flock of crows, before multiplying.

2. 'Like A Prayer'

1989

Chock-a-block with controversy-igniting religious imagery (crosses on fire, stigmata, Madonna making out with a saint), the unforgettable video for the gospel-inflected pop hit (complete with choir) ranked high among your votes earning the second slot on this list.

1. 'Vogue'

1990

It has style, it has grace, and yes, in it, Madonna "gives good face." Another fruit of Madge's perfect pairing with director David Fincher, this 1990 homage to the sirens of the silver screen, complete with gauzy black-and-white cinematography and an irresistible matching dance, took the No. 1 spot in your votes in a landslide.

Madonna's Fashion Evolution: 50 Iconic Looks | Madonna's 40 Biggest Billboard Hits

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