However, trouble began to manifest in Madonna's personal and professional career at about the time she married Sean Penn. Although both were similar in their fiery, rebellious personalities, Sean's love for privacy clashed drastically with Madonna's obsessive need for public adoration and attention. As paparazzi and the press increasingly entered the life of the famous couple, Sean's desire for remoteness was violated too many times. On several highly-publicized occasions during the marriage, Sean's unpredictable and volatile temper was unleashed on the press. Starting with the chaos of their helicopter-invaded wedding to the allegations of domestic violence perpetrated against Madonna, the Penn-Madonna marriage was fraught with controversy, altercation, and constant clash with the world-at-large.

As Madonna's private life was fraught with durm und strang, the smoothness that had blessed the beginning of her career was also beginning to show signs of turbulence and disruption. Sean and Madonna were involved in the much-ballyhooed bomb of a movie, Shanghai Surprise. So abysmal were all facets of the film that it nearly sunk George Harrison's production company HandMade films, the party responsible for the film. This was the first scar in Madonna's otherwise unblemished career.

This entire period of tempestuousness, unpredictable behavior, and career setbacks coincided with a once-in-a-lifetime transiting Uranus conjoining Madonna's Saturn. (see chart) This transit has the potential of being one of the most disruptive and psychologically stressful periods of one's life. It is the transit of crisis simply because the energies of Saturn and Uranus are so diametrically opposed. With Saturn and Uranus, one grounds an electrical storm; high voltage energy is forced to contend with structure and earthy reality. Of the transit, astrologer Rob Hand states, "It is often a time of great tension and sudden releases of tension."(10) Certainly Sean Penn's unpredictable outbursts and sudden acts of hostility would have fit this description for Madonna. When shooting on location for Shanghai Surprise, Madonna stated of the storminess and turbulence surrounding her and Sean, "When we got to England, it was like the Third World War."(11) The frenetic quality, controversy and darkly chaotic energy of the Saturn-Uranus arrangement certainly can be experienced as warlike in its high-pitched intensity and bombast. However, as with all tests involving Saturn, Madonna emerged stronger, more resilient, and more mature.