The following is condensed from an article at the website of Facing The Challenge, a Christian ministry located in England.
By Jock McGregor
February 2001 – With a personal fortune of well over $70 million and sales of over 85 million albums worldwide, Madonna has become one of the most successful and notorious female singers the world has ever seen. In insightful ways she is a cultural icon of postmodernism.
Image is everything. Madonna's whole life revolves around the presentation of her image. She lives totally within the artificially constructed reality of the image. But she is not alone in that. This is central, not just to Madonna, but also to our culture. Increasingly we see the blurring of image and reality. In politics, style replaces substance; in commerce, packaging and promotion replace quality; in society, how you look replaces who you are; form replaces content; the outer presentation replaces the inner reality. So many people live out their lives vicariously, through the image world of media, TV, soap operas and armchair sports. Life has become virtual. Like Madonna, you just live in the image.
Image is constantly changing. She is always changing her image, whether it is from the good girl gone bad to the virgin in white; from Marilyn Monroe to the 1920s gangster moll, from androgynous, cold robot to naked sex symbol; from glamour queen to cosmic spirit and finally to doting mother. Again, this reflects our culture. We are always looking for the new, always moving from one image to the next, swapping one artificial world for another.
Madonna's use of image is complicated in a further way, because while she lives in her images, she refuses to fully identify with them. She says: "I do everything with a wink." Once again, this ambivalence--on the one hand living in an image world, but on the other hand never quite committing to it--is very reflective of our present culture.
So Madonna stands in one place, one image, and she cannot ever escape that image because there is no objective reality. But at the same time she can never commit to that image, since she realizes that with time she will take on another. So there is no commitment. And anyway, why commit to something you know is not real?
And so it is with our culture. We are adrift in a sea of sub-cultural alternatives with no fixed point to guide us, no solid ground to stand on, no firm foundation on which to build our lives. We are a generation of floaters, of drifters. We have the world at our feet, but no place to rest our head. 
