Amy Winehouse has been rebelling since an early age when she was expelled from school at the age of 12 for piercing her own nose. Her music career began with her own rap duo at age 10. She started playing guitar at 13 and at by the age of 20 her first album was released. She is an incredibly creative woman, with loads of talent and a provocative and unabashedly raw and honest display of herself that defies any effort to categorize or define her.

In 2006 Amy fired her management company for trying to “stick” her into rehab, and then wrote a song about the experience. Although for a long time she denied having a drug and alcohol problem, she appeared drunk and stoned on several television shows last year and has admitted to being troubled by bulimia and eating disorders as well as a temper and a tendency toward violent behavior.

This year Amy has won an astonishing number of musical awards but has also appeared frequently in the tabloids due to her bizarre behavior. In May she married her new husband after a month-long courtship, and several weeks ago the two of them entered rehab after a 3-day bender of multiple drugs and alcohol that left Amy in a coma. They walked out after five days. Subsequent to that she cancelled her summer concerts, and most recently cancelled September concerts as well.

Amy Winehouse is a Virgo (see chart), the sign known for its reticent and modest behavior which just shows how little validity Sun Sign astrology has. There is another brand of Virgo which some call the “Radical Virgo” in which the famous Virgo powers of analysis and perfectionism are combined with other elements in the chart to create a more reactionary personality. Amy’s chart shows six planets in fire signs which keep her locked forever in a battle between the conservative side of her Virgo nature and the urge that the fire element evokes for a freer life.

Her Sun is squared by Neptune, the planet that dissolves the boundaries of ordinary reality. While this combination stimulates tremendous creativity, there can also be difficulty establishing boundaries and confusion over one’s own identity as defined by the Sun. Neptune conjoins her Moon which is another significator for creative brilliance as well as musical ability, but again there is a struggle to keep one’s feet on the ground. This strong Neptunian signature often suggests an individual who is either a saint or a drunk as the desire to transcend reality can go in either direction.

Amy’s Venus and Mars are conjunct in Leo, illustrating her huge need for attention and admiration that is Leo’s birthright. She has a flair for the grand gesture and a tremendous appetite for experience. There is another conflict here as well, in that the Virgo nature prefers to shun the spotlight but Mars in Leo has a tremendous drive for fame.

The placement of Jupiter, planet of abundance and opportunity, in Sagittarius shows an underlying optimism and faith but also a tremendous need to escape from any confinement. The conjunction of Jupiter to the planet of rebellion, Uranus, indicates an extremely radical individual who is fiercely independent.

This conjunction of Jupiter and Uranus is opposed by Chiron, a small planet in the Kuyper belt that signifies the Wounded Healer. When in a difficult aspect to other planets, Chiron indicates a deep psycho-emotional wound that doesn’t heal, but which ultimately serves as the guide to the individual’s ability to heal themselves. In Amy’s chart, Chiron is in Gemini which shows that this deep wound for her is in her ability to express herself to others. We see another indicator of that in the fact that Mercury is retrograde in her chart (meaning it appeared to move backwards at the time she was born). Chiron is also retrograde, suggesting that this wound runs deep. The opposition of Chiron to Uranus, which is not uncommon in individuals born between 1955 and 1985, has a well-documented tendency to evoke addictive behaviors because of its intense effect on the nervous system.

This is a dramatic combination of diverse planetary influences that can be difficult to reconcile, and Amy’s strong Neptunian influence facilitates her amazing creative expression but also creates delusion and illusion in her life. This influence was heightened over the past year as transiting Neptune opposed Mars and Venus in her chart, weakening her resolve (Neptune/Mars) and creating confusion in relationships (Neptune/Venus). This is the beginning of a cycle that began last year and will continue over the next few years, bringing Amy to the brink of disaster in order to force her to make hard choices.

Next year won’t be any easier for Amy – transiting Saturn will be making a square to the painful Chiron in her chart, and squaring Jupiter and Uranus as well. Saturn cycles impose limitation and restriction and urge us to do the hard work of introspection and apply discipline in all aspects of our lives. When Saturn and its restrictions hits the rebellious urges of Jupiter and Uranus, life can be difficult unless we force ourselves to do the work that is required and delay our personal gratification for the time being. This cycle will continue through next summer for Amy and could mark either her greatest productive period yet, or her most painful.

Another intense planetary cycle for Amy is the passage of transiting Pluto over her Moon/Neptune conjunction. Pluto cycles bring dramatic change as we are forced to let go of things from the past that no longer serve us in our evolution forward. Pluto cycles are intense and can be difficult, but also bring about exhilarating change as we become more completely the person we are meant to be.

Life isn’t always easy, and it is more difficult for some than for others. But inherent in every challenging birthchart is the gift of transformation, and let us hope that Amy is able to balance her difficulties before she does serious damage to herself.