For essentially five years, as Madonna experienced Pluto transits to her Sun and to her natal Pluto, (see chart) Madonna explored the question "Why is it so good to be so bad?" and most of us publicly deplored and chastised Madonna for her adolescent self indulgence, while privately we were curious to see how low she could go. Arguably, no popular artist of Madonna's stature so obsessively "raised Cain" with such overt and explicit self-transparency. From roughly the period of her controversial, banned video, Justify my Love created in late 1990 until the release of Human Nature in 1995, Madonna explored—immersed herself in, rather—the sexual, the orgiastic, the pornographic, the explicit, the taboo. Throughout Madonna's long, dark period, Pluto was making a slow transiting square to both her natal Sun and Pluto.

Madonna didn't score points for subtlety or self-restraint during this phase of her career. Like a young child testing parental boundaries with incessant "poopey" jokes, Madonna assaulted her audience with the fact that for an extended period she was engrossed in the potency and primacy of the Id—and reveling in it. Biographer Mark Bego muses on the phase: "After a bestselling book about sex, a double-platinum album about sex, two disastrous films about sex, and her verbal-fuck fest on the Letterman show, she lost some of her appeal and her audience."(14)

How does one evaluate this period? Usually we give highest marks to those artists that are able to redeem, sublimate, or transform this particular dimension of human experience. It obviously takes a lot more effort, energy, and thought to take what's in the bowels and depths and converting it. Yet, there is something quite significant and powerful to what Madonna exposed during this period. She's doing our dirty work for us. The theory in astrology is that after a planet is discovered, we learn how to handle and best utilize its energies. After Pluto was discovered in 1930, we became much more in touch with the primal energies of the human unconscious. However, many of us would like to pretend that this didn't ever happen. Madonna was in all actuality doing something that most people are extraordinarily frightened of doing—integrating in a very obvious and apparent manner the primal power associated with Pluto. If indeed Madonna was posing the question for herself and for all of us, "Why is it so good to be bad" then the answer is: "that it is better to be whole than good."